Every Single ‘Chappelle’s Show’ Sketch (Except One), Ranked
Photo sources: Comedy Central

Every Single ‘Chappelle’s Show’ Sketch (Except One), Ranked

Three seasons. Twenty-eight episodes…

By the time comedian Dave Chappelle was a 14-year-old prodigy turning heads in Washington, D.C.’s stand-up clubs, he was already building the foundation for what would become the most groundbreaking sketch show of the 21st century. The skinny minister’s kid was not yet ready to tackle adult-themed humor in 1987, but he wasn’t afraid to explore the dangerous minefield of race that would fuel much of the success of his genre-shifting series, Chappelle’s Show.

“Jesse Jackson was running for president, so I used to do jokes about that,” he told NPR’s Fresh Air back in 2005, alluding to the Black civil rights icon’s second run for the White House. “I’d talk about stuff I saw on TV, like Alf. But they all had race in them, one way or another. Alf, my whole thing, was like, an alien comes 3 billion miles from space and gets a home with a White family… which all sounds corny now, but remember, I was 14, so it was like, wow.”

When Chappelle’s Show premiered on Comedy Central on January 22, 2003, it didn’t just disrupt the predominantly vanilla basic cable television landscape—it became a pop culture phenomenon. Along with writing partner Neal Brennan and co-executive producer Michele Armour, Dave Chappelle unleashed a provocative, smart, and at times dangerous sketch comedy show that dissected stereotypes, slavery, reparations for Black Americans, politics, and gender wars — and that was all just in the first season.

By 2004, Chappelle’s Show had become one of the top-rated programs on cable in its time slot (and number one in the much coveted men ages 18 to 34 men demo), averaging 3.1 million viewers. Chappelle’s Show: Season One Uncensored now ranks as the bestselling TV-on-DVD title of all time, moving nearly 3 million copies. Not only did the show transform its laidback host into a comedy icon, but it also reintroduced the legendary likes of Paul Mooney to a younger audience, gave a platform to a who’s who of hip-hop innovators and headlining performers, made Charlie Murphy and Donnell Rawlings into legit stars, and introduced future stand-up rebel Bill Burr.

And then Chappelle waved the white flag.

After signing a $50 million deal with Comedy Central and starting production on the third season, Chapelle decided in 2006 that he wanted no part of the juggernaut he’d created. Citing an overwhelming fear that (White) people were laughing at his racially charged sketches for all the wrong reasons, Chappelle hightailed it to Africa to recharge.

In its brief yet indelible run, Chappelle’s Show gave a striking nod to the irreverent, unapologetically Black sketch comedy of Keenan Ivory Wayans’ In Living Color (1990–1994) and Eddie Murphy’s game-changing run on Saturday Night Live (1980–1984). Yet Dave Chappelle pushed the limits even further. In arguably the series’ most controversial skit, Clayton Bigsby, the world’s only Black White supremacist, the incendiary word “nigger” is dropped 17 times.

Today, stand-up specials like Killin’ Them Softly, For What It’s Worth, The Bird Revelation, Sticks & Stones, and 8:46 have solidified Chappelle’s status. (Not many would dare to do a “routine” on the global protest movement–igniting police murder of George Floyd without even attempting to induce a laugh.) But while the winner of the prestigious 2019 Mark Twain Prize for American Humor is often hailed as Richard Pryor’s worthy successor — a subversive, counterculture voice — he’s no longer untouchable.

Chappelle has been criticized for frequent jokes about the LGBTQ community, a firestorm that reignited following the premiere of his special Sticks & Stones. For many, his punchlines about the “alphabet people,” and more specifically transgender folk, have exposed an artist who is progressive on many issues, yet a relic on others.

That’s just one of many reasons why ranking all 112 sketches of Chappelle’s Show is such an arduous effort. Not only are we dealing with some of sketch comedy’s greatest works, but there are also artistic misses and cringeworthy embarrassments. (Indeed, one entry we excluded altogether is Chappelle’s R. Kelly parody video “Piss On You.” With the R&B singer behind bars in Illinois, facing charges including racketeering, child pornography, and violations of the Mann Act, the LEVEL team did not see the value of highlighting a sketch that specifically joked about underage sexual abuse.).

But there are classics as well — and plenty of ’em. From the aforementioned Clayton Bigsby to Tyrone Biggums, Ask a Black Dude to the Racial Draft, from True Hollywood Stories to the Niggar Family, breaking down every sketch from Chappelle’s Show’s 28 episodes is the closest we’ve ever come to understanding what makes the complex Dave Chappelle tick.

111. ‘Third World Girls Gone Wild’ (2003)

Aired: Season 1, Episode 6
Headliners: None Genre: Commercial parody Classic Quote: “No collection of videos showing girls lifting their shirts up is complete without National Geographic’s Third World Girls Gone Wild!”

Chappelle’s Show’s parody of convicted T&A mogul Joe Francis’ exploitative series Girls Gone Wild is dragged down by some pretty unimaginative mocking of African tribe culture. A stereotype-riddled misfire that thankfully doesn’t extend beyond 26 seconds.

110. ‘Frontline’: In a Gay World (2004)

Aired: Season 2, Episode 11
Headliner: Dave Chappelle Genre: Mockumentary Classic Quote: “Have you considered going back to Africa?”

The first appearance on our list of Chappelle’s Show’s frequent parodies of PBS series Frontline never reaches the brilliant heights of its franchise mates. Brought out only in an episode dedicated to unaired material, the sketch has enough dusty gay jokes (a queer boxing match is announced as “Friday Night Sissy Fights”) to give credence to why the Charlie Murphy co-penned satire had been previously left on the cutting room floor.

109. Diarrhea Choir (2003)

Aired: Season 1, Episode 12
Headliner: Dave Chappelle Genre: Musical spoof Classic Quote: “Diarrhea, diarrhea…”

In response to a People magazine reporter claiming that his show is sophomoric, Chappelle conducts a choir in a full-throated rendition of a classic childhood song.

108. Truf.com (2003)

Aired: Season 1, Episode 4
Headliner: Dave Chappelle Genre: Commercial parody Classic Quote: “And you know they’re not bad after unprotected sex with multiple partners, either.”

In this sardonic take on the memorable smoking PSA, Chappelle offers his anti-anti-cigarette philosophy.

107. New York Boobs (2003)

Aired: Season 1, Episode 4
Headliner: Dave Chappelle Genre: Man on the street Classic Quote: “They rest on my arm like an eagle on a perch. These are some of the best boobs you can see in the city.”

Future N-bomb-dropping podcast superstar Joe Rogan and a mustached Chappelle walking around Times Square awarding blue ribbons to women’s breasts? Yeah, it’s as cringeworthy as you can imagine.

106. What Men Want (2003)

Aired: Season 1, Episode 8
Headliners: Hannah Dalton, Michael Isaiah Johnson Genre: Movie spoof Classic Quote: “Damn!”

A flip of the 2000 romantic comedy What Women Want, viewers get a peek inside the dirty, foul minds of misogynistic, woman-harassing men (and one little boy who clearly needs a time-out). The premise has potential but misses the mark by not making the dudes the butt of the joke.

105. “Minorities” in the News (2006)

Aired: Season 3, Episode 3
Headliner: Russell Simmons Genre: Fake news Classic Quote: “You know, Lisa, for the past two years there’s been a spike in nigger entrepreneurship here in America…”

The problem isn’t in this initially unaired bit’s lampoon of how the media hides behind such euphemisms as “minorities” and “special interests.” It’s that it runs like an incomplete thought that’s made all the shakier by the appearance of preaccused sexual assaulter and disgraced hip-hop mogul Simmons.

104. Two-Minute Special (2003)

Aired: Season 1, Episode 9
Headliner: Dave Chappelle Genre: TV parody Classic Quote: “They did come up with enough money for me to do a two-minute special.”

So, what does a two-minute comedy special looks like? Ridiculously short.

103. Watching TV While Having Sex (2006)

Aired: Season 3, Episode 2
Headliners: Dave Chappelle, Alf, Charles Barkley, Marla Gibbs Genre: Situation comedy Classic Quote: “Watch me take it to the hole!”

Dave has sex with the TV on. Just… no. Bad idea.

102. Black Howard Dean (2006)

Aired: Season 3, Episode 2
Headliner: Dave Chappelle Genre: Political satire Classic Quote: “Byaaah!!!!”

There was a moment when the onetime presidential candidate’s nonsensical 2004 Iowa Democratic caucus battle cry became go-to material for damn near every talk show host, political pundit, and comedian. But what starts off as a fun political bit quickly turns redundant.

101. ‘Inside Chappelle’s Show Studio’ (2003)

Aired: Season 1, Episode 5
Headliners: Dave Chappelle, William Bogert Genre: TV parody Classic Quote: “May I have a cheeseburger, large fry, and something cold to drink!”

In this obvious mocking of the late James Lipton’s Inside the Actors Studio, Dave sits down for a pretentious interview with Frontline host Kent Wallace (Bogert) to discuss his celebrated 74-plus film career. Although it kicks off in the right direction by completely nailing an Oscar-bait war film — complete with a Black soldier’s overdramatic death and White savior trope — this inconsistent premise should have ended there.

100. Stereotype Pixies/Audience Feedback (2006)

Aired: Season 3, Episode 2
Headliners: Dave Chappelle, Guillermo Diaz, Charo, Yoshio Mita, La La Anthony, Dimitri Meskouris Genre: Situation comedy Classic Quote: “What happened to some good ol’ fashioned pancake butt? Now that’s what Mom used to make. Nice and flat.”

The sketch that essentially ended Chappelle’s Show. Indeed, this shelved series of vignettes — in which Dave plays a devilish pixie who offers the most racially stereotypical advice to Black, Latino, Asian and White men — was so provocative that producers had Charlie Murphy and Donnell Rawlings conduct a Q&A session to discuss the segment when it aired on “The Lost Episodes” (as the third season was branded).

In one scene, Dave — as a magical blackface creature — pushes his real self to eat fried chicken in front of White people on a flight. Chappelle was horrified by the reaction from a White spectator who was on the set. “When he laughed, it made me uncomfortable,” Chappelle told TIME back in 2005. “As a matter of fact, that was the last thing I shot before I told myself I gotta take fucking time out after this. Because my head almost exploded.”

The Latino version, featuring Guillermo Diaz and Charo, also touches the offensive third rail, but the Asian version is downright deplorable, with Dave sporting buck teeth, a Fu Manchu mustache, and speaking broken English. But as one audience member noted during the post-screening discussion, Dave’s White pixie jokes were downright innocuous (the old “White folks have no rhythm” gag, basically). Not one of his better moments.

99. Love Contract (2004)

Aired: Season 2, Episode 4
Headliners: Dave Chappelle, Rashida Jones Genre: Commercial parody Classic Quote: “Kobe!”

It’s interesting watching a sketch in which Chappelle’s character has Rashida Jones’ sign laughably intricate paperwork for consensual sex more than a decade before the #MeToo movement empowered women to speak out against sexual assault. That doesn’t mean “Love Contract” isn’t amusing — especially since it came out right as the real thing was gaining traction. It just doesn’t rank among the show’s wittiest ad parodies.

98. QVC Meltdown (2003)

Aired: Season 1, Episode 3
Headliners: Nick Wyman, Lynne Wintersteller, Angelique Doudnikova Genre: TV parody Classic Quote: “I think you have a booger on your hand.”

Everything that could go wrong on this QVC program does — and horribly.

97. Holler Dating Service (2004)

Aired: Season 2, Episode 11
Headliner: Anthony Berry Genre: Commercial parody Classic Quote: “Holla, holla, holla…”

As a standalone riff, Berry’s unhinged “Holla Man” works because it’s a quick hit that exists without any contrived pretense. But when you try to shoehorn it into a sketch in which an online service hires dudes to hit on women outside a bathroom, it loses much of its ridiculous charm.

96. Dudes’ Night Out (2004)

Aired: Season 2, Episode 10)
Headliners: Dave Chappelle, Bill Burr, Donnell Rawlings Genre: Commercial parody Classic Quote: “A mouth’s a mouth, man.”

Apparently, if you drink Schlipp’s Beer, you’ll instigate a bar fight, piss and shit on a restaurant sidewalk as diners look on with disgust, cry, and rip on your boys for getting with three trans sex workers. No chance this one would get a green light in 2020.

95. iMac Commercial (2003)

Aired: Season 1, Episode 4
Headliner: Dave Chappelle Genre: Commercial parody Classic Quote: “I’m a chronic masturbator.”

When Apple shipped more than 3 million Macs across the globe in 2003, the groundbreaking Technicolor desktop reportedly accounted for 72% of the company’s revenue. So of course Dave offers up a bawdy poke at the iconic computer — which, according to him, makes watching porn while listening to the Wu-Tang Clan a snap.

94. Real Movies: ‘The Matrix,’ ‘Pretty Woman’ (2003)

Aired: Season 1, Episode 7
Headliners: Dave Chappelle, Amanda Serkasevich, James Riener Genre: Movie spoof Classic Quote: “Okay… you gotta get the fuck out of here.”

While the sketch’s comical nod to The Matrix never goes anywhere, its hardcore take on Pretty Woman flourishes as Julia Roberts’ hooker with a heart of gold is kicked out of bed after making unsolicited small talk.

93. Hip-Hop News: Wu-Tang Torture (2006)

Aired: Season 3, Episode 1
Headliner: Dave Chappelle Genre: Fake news Classic Quote: “First he put my nuts on a dresser. It was crazy… just my nuts. Then he banged them shits with a spiked bat.”

Method Man and crew bring the ruckus — and a heated coat hanger — as their classic album skit comes to life.

92. ‘HBO: Real Sex Street’ Interview (2003)

Aired: Season 1, Episode 2
Headliners: Sophina Brown, Dave Chappelle Genre: TV parody Classic Quote: “The craziest thing I ever did sexually? It’d probably be having sex with ol’ Gang Bang here without a rubber.”

When Dave’s girlfriend admits to having a freaky threesome with two dudes during an on-the-street interview with the infamous HBO verité series, things go delightfully downhill.

91. Black Gallagher (2004)

Aired: Season 2, Episode 2
Headliner: Dave Chappelle Genre: Situation comedy Classic Quote: “Black Gallagher don’t go out like no punk bitch with a mallet!” (Runners-up include “I got warrants!” and Neal Brennan yelling, “Smash some fruit, you Black sonofabitch!”)

Telling jokes and smashing inanimate objects works for the real Gallagher — but that’s not good enough for Chappelle’s version, who takes out a gun and shoots a watermelon before accidentally killing an audience member. [Frankly, I can’t believe this one is ranked so low. — Ed.]

90. Dave on ‘Donahue’ (2003)

Aired: Season 1, Episode 4
Headliner: Dave Chappelle Genre: Situation comedy Classic Quote: “That’s a lot better than saying, ‘Hey, that nigga’s homeless.’”

Not so much a comedic statement, but a serious defense of affirmative action and a middle finger to angry, racist White men. A clip from Chappelle’s appearance on The Phil Donahue Show seamlessly works as a setup to one of the series’ most celebrated skits: “Reparations 2003.”

89. Def Poetry Jam (2004)

Aired: Season 2, Episode 11
Headliners: Mos Def, Dave Chappelle Genre: TV parody Classic Quote: “When White people’s power goes off, they panic. When Black people’s power goes off, they planned it.”

Dave imagines Def Poetry Jam as a showcase for excessively corny jokes in this mildly entertaining, previously scrapped sketch.

88. Campaign Advertisements (2004)

Aired: Season 2, Episode 1
Headliner: Dave Chappelle Genre: Political satire Classic Quote: “God damn, that’s gross.”

Chappelle wants your vote. And his platform is tackling teen pregnancy. “What we need is more programs in place that promote abstinence,” he says. His solution? Every high school principal has sex with the oldest teacher in front of the students… covered in mayonnaise. Yeah, that’ll do it.

87. Real Movies: ‘Half Baked’ (2003)

Aired: Season 1, Episode 8
Headliners: Dave Chappelle, Jim Breuer, Guillermo Diaz Genre: Movie spoof Classic Quote: “Yo, Fuck Kenny, B!”

“Real Movies” takes a more grounded approach to some Hollywood favorites as the 1998 cult classic film Half Baked gets new life, reuniting stoner heroes Thurgood (Chappelle), Scarface (Diaz), and Brian (Breuer). But this time around, instead of concocting a wild scheme to bail their roommate and friend Kenny out of jail, they decide to stay home and smoke weed. Nice.

86. Nat King Cole Christmas (2003)

Aired: Season 1, Episode 1
Headliner: Dave Chappelle Genre: Musical spoof Classic Quote: “King Cole Records coming at you. We sip only the best Dom P because I’m smooth like that.”

The legendary Nat King Cole is reenvisioned as a sexist hip-hop star hosting a 1956 Christmas special. There are a few chuckles here for sure, but the fact that it’s inspired by Dr. Dre spraying malt liquor on a woman in the 1992 “Nuthin’ But a ‘G’ Thang” music video offers a low-key critique.

85. Crazy Camera (2003)

Aired: Season 1, Episode 11
Headliners: Dave Chappelle, Carson Daly, Donnell Rawlings Genre: Situation comedy Classic Quote: “Will you little fuckers shut up?!!! How excited can you really be for a video you’ve seen 58 times in a row?”

Squeaky-clean MTV host Carson Daly letting off a series of F-bombs at precocious preteens is far and away the standout moment in an otherwise ordinary sketch in which Dave purchases a magic camera that gives him the ability to not only see a person’s future but also film their innermost thoughts and expose their true self. Clocking in at a little over seven minutes, “Crazy Camera” would have been even more satisfying if it were cut in half.

84. Wrap It Up Box (2003)

Aired: Season 1, Episode 2
Headliners: Dave Chappelle, Melle Powers, Guillermo Diaz Genre: Commercial parody Classic Quote: “Wrap that shit up, B.”

Awards shows are long enough without having to deal with laborious 10-minute acceptance speeches of actors thanking their agent, mom, first roommate, and therapist. If only we had the same cue music that rushes longwinded celebrities off the stage. Wish no more — in Chappelle’s vision, you can shut down just about any everyday nuisance, whether you’re on a bad date, you want a court judge to pipe down, or you want to put an abrupt end to horrible sex.

83. Great Moments in Hookup History (2003)

Aired: Season 1, Episode 8
Headliner: William Bogert Genre: TV parody Classic Quote: “When you’re that young and horny, you have nothing to lose.”

Danny Cory becomes the first pervert to use the infamous “penis in the popcorn” trick while on a movie date. But it’s shameless narrator James “Skank” Scanton (played with degenerate enthusiasm by the late William Bogert) that elevates this third installment of Chappelle’s exploration into douchebaggery.

82. Home Stenographer (2003)

Aired: Season 1, Episode 1
Headliners: Dave Chappelle, Sophina Brown, James Ludwig, Brett Tabisel Genre: Commercial parody Classic Quote: “I guess if it came down to it, I would bang Ben Affleck.”

Imagine if you had your own personal stenographer to transcribe everyday conversations. Chappelle delivers that absurd scenario with mixed results. And when we get to the moment where a bespectacled, elegantly dressed little person strapped to the back of a man reads back his friend’s drunken fantasy of hooking up with a Hollywood actor, the sketch reaches its full potential.

81. Negrodamus (2004)

Aired: Season 2, Episode 2
Headliner: Paul Mooney Genre: TV parody Classic Quote: “Star Jones will have two jobs. First she’ll do The View. Then she’ll take her wig off and do the weather.”

Legendary comedian and outspoken race man Paul Mooney as a truth-telling, no-nonsense Black prophet? Perfect.

80. A Moment in the Life of Lil Jon (2004)

Aired: Season 2, Episode 6
Headliner: Dave Chappelle Genre: Situation comedy Classic Quote: “Okaaay!”

Chappelle’s hearing-impaired super producer, Lil Jon, makes some much-needed flight reservations. Not the best version of Chappelle’s impression, but definitely one of the loudest.

79. Real Movies: ‘Ghost’ (2003)

Aired: Season 1, Episode 8
Headliner: Dave Chappelle Genre: Situation comedy Classic Quote: “Hey, Molly — your husband’s clothes fit funny, girl.”

The 1990 fantasy romance classic gets cold-blooded when Dave sleeps with Demi Moore’s Molly after Patrick Swayze’s Sam is murdered — and then taunts Sam’s brokenhearted spirit: “Oh nigga, you know I see you.”

78. A Moment in the Life of Lil Jon (2004)

Aired: Season 2, Episode 7
Headliner: Dave Chappelle Genre: Situation comedy Classic Quote: “Whaaat!”

Lil Jon goes to the doctor’s office after injuring his arm. The delirious exchange that ensues proves that a one-note punch line can sometimes go a long way.

77. Dave’s Educated Guess Line (2003)

Aired: Season 1, Episode 2
Headliner: Dave Chappelle Genre: Commercial parody Classic Quote: “It’s six weeks later. You’re going right back into jail for the same shit.”

It’s like the Psychic Readers Network, except Dave doesn’t even pretend to be clairvoyant like the late Miss Cleo. He’s “merely a racist who believes that stereotypes dictate our futures.” So when a woman confides that her boyfriend thinks her butt is too big and that her previous man loved her shape, Dave deduces that… her boyfriend is White and her former partner is Black. Shocker!

76. Great Moments in Hookup History: Bobby Hutchinson (2003)

Aired: Season 1, Episode 7
Headliner: Dave Chappelle Genre: TV parody Classic Quote: “You give me Pac-Man fever. Wakka wakka wakka…”

It’s the 1980s, and Bobby Hutchinson (Chappelle), looking like he just stepped out of Michael Jackson’s “Beat It” video, is on the hunt to get laid. The problem? His would-be conquest, Gina Morris, is protected by two friends who between them have racked up 14 “cock blocks.” Of course the thirsty bastard makes the winning play amid spot-on voice narration that could easily be mistaken for one of those old-school NFL Films features.

75. Roca Pads (2003)

Aired: Season 1, Episode 5
Headliners: Liz Beckam, Rashida Dash, Damon Dash Genre: Commercial parody Classic Quote: “I got something that will keep your motherfucking flow tizzight!”

If rap moguls can sell clothing, sneakers, and liquor, then why not menstrual pads? Former Roc-A-Fella CEO Dame Dash presents Roca Pads. Yes, it’s as bonkers as it sounds.

74. Ask a Black Dude: Size Matters (2003)

Aired: Season 1, Episode 10
Headliner: Paul Mooney Genre: Q&A Classic Quote: “You know they’re not going to let a nigga have nothing… they take everything. They took Tina Turner. They took Michael Jackson. They took James Brown and gave him back.”

Mooney has some thoughts on why there are so many mixed couples. “Brothers are packing,” he notes. “White girl ain’t that crazy.” Goodnight, folks!

73. The Three Daves (2004)

Aired: Season 2, Episode 3
Headliners: Dave Chappelle, Amir Ali Said Genre: Situation comedy Classic Quote: “I’m broke, nigga, I’m broke!”

Dave breaks down how his 18-, 24-, and 30-year-old selves handle various scenarios. It’s worth a glimpse just to see a 1982-era Chappelle rocking a Cross Colours–style outfit; telling his girlfriend, “I riggity-realize that I liggity-love you,” as if he was the third member of Das EFX; and reciting lyrics from Wreckx-n-Effect’s booty anthem “Rump Shaker.” Pay close attention to the bit in which Dave loses out on a film role to Nick Cannon and admonishes his son for being a fan of the Drumline star — the gag comes full circle in a future episode.

72. Ask a Gay Dude (2003)

Aired: Season 1, Episode 6
Headliner: Mario Cantone Genre: Q&A Classic Quote: “I’ll put a Band-Aid over your left cheek and make you my Nelly.”

Maybe “Ask a Gay Dude” was Chappelle’s way of acknowledging his own awkward, at times offensive views on gay culture. Years before he received pushback for what many perceived as transphobic jokes, Dave offered comedian and Sex in the City actor Mario Cantone the floor to respond to questions that at times tread into homophobia territory. The clapback is as hard as it is hysterical.

71. Great Moments in Hookup History: Martin Johnson (2003)

Aired: Season 1, Episode 5
Headliners: Dave Chappelle, Melle Powers, J. Emerson McGowan, Donnell Rawlings Genre: TV parody Classic Quote: “Can anybody take this drunk, horny, crazy woman home?”

More NFL Films lampoonery. This time, a stoic narrator gives viewers a play-by-play breakdown of Martin Johnson (Chappelle), a man so “desperate for ass” that he tries to take home a beyond-inebriated woman nicknamed Ashley “Smashly” Evans (Melle Powers). Despite league bad boy Jimmy Mackey (Rawlings) pulling off a clutch interception, Johnson prevails. As farcical as it is, it’s hard to look past the fact that the entire premise hinges on taking advantage of an incapacitated woman.

70. Mooney on Movies (2004)

Aired: Season 2, Episode 7
Headliners: Paul Mooney, Celina Lorenz, Allison Walton Genre: TV parody Classic Quote: “First they have The Mexican with Brad Pitt. And now they have The Last Samurai with Tom Cruise. Well, I’ve written a film: The Last Nigger on Earth, starring Tom Hanks.”

Mooney and two White women discuss the slavery-glorifying 1939 epic Gone With the Wind, among other flicks. Buckle up, folks.

69. When Keeping It Real Goes Wrong: Vernon Franklin (2004)

Aired: Season 2, Episode 7
Headliner: Dave Chappelle Genre: TV parody Classic Quote: “Allow me to reintroduce myself. My name is Hov!”

So, what do you do when your White boss congratulates you with some insulting, stereotypical Black jive talk? If you’re Vernon Franklin (Chappelle), the first in his family to graduate college and the youngest vice president at Viacorp Corporation, you hopefully keep cool and move on. But of course, this is Chappelle’s Show, which means Vernon curses out his superior, physically threatens co-workers, and is possessed by the very much alive spirit of DMX.

68. Life Like a Video Game (2003)

Aired: Season 1, Episode 9
Headliner: Dave Chappelle Genre: Situation comedy Classic Quote: None

You don’t have to be a hardcore gamer to be entertained by the unbridled wackiness of this one, wherein Dave goes through his daily life as if he were in the controversial video game series Grand Theft Auto. There’s a carjacking, plenty of senseless violence, and a Vice City HUD interface accurate enough to tell you that someone on the writing team was a serious GTA head.

67. Nelson Mandela’s Boot Camp (2004)

Aired: Season 2, Episode 11
Headliners: Dave Chappelle, Sally Jessy Raphael Genre: TV parody Classic Quote: “I would tell him that I would squeeze his breasts together and make love to his bosom.”

“This is where the sketch goes completely wrong,” muses Chappelle, while gleefully showing what was once relegated to the cutting room floor. That’s an understatement. Nelson Mandela’s Boot Camp is completely bananas even for a blissfully unmoored series like Chappelle’s Show. There’s Dave as the beloved freedom fighter, wearing a purposefully god-awful wig that would make Tyler Perry do a double take. There’s Mandela beating up juvenile delinquents. He later jacks a boot camp inmate’s stash of weed, smokes it, and joins the kids in a rendition of “The Lion Sleeps Tonight.” Someone was definitely high writing this one.

66. If the Internet Was a Real Place (2004)

Aired: Season 2, Episode 6
Headliners: Dave Chappelle, Anthony Berry, Ron Jeremy Genre: Situation comedy Classic Quote: “Spambusters, bitch!”

Dave enters a world transformed into the internet. There are some decent gags here as Chappelle beats down annoying pop-up windows (degenerates pushing penis enlargement, a debt consolidator, and gambling stalkers), views Paris Hilton’s infamous sex tape (hey, it’s 2004), and watches some head-shaking porn involving goats. Wild. But the cameo by adult film star Ron “The Hedgehog” Jeremy, who has recently been the subject of multiple sexual assault accusations, aged about as well as… well, Ron Jeremy.

65. Marijuana PSA (2004)

Aired: Season 2, Episode 7
Headliners: Dave Chappelle, Jim Breuer, Guillermo Diaz Genre: Commercial parody Classic Quote: “If you are a girl under the age of 12 and you’re high on marijuana, don’t ride your bike.”

The Half Baked crew turns a memorable marijuana PSA on its head. When the weeded-out trio accidentally drives over a child riding a bike in the drive-thru at WacArnold’s (a nod to Dave’s favorite fictional burger joint), things get dark. Diaz suggests they chop her up — only for the kid to pop back up, freaking out the mega-blowed crew. The best part? It’s aimed not at the dumbasses driving impaired, but at the high-ass 12-year-olds riding their bikes near traffic.

64. Diversity in First Class (2003)

Aired: Season 1, Episode 5
Headliner: Dave Chappelle Genre: Political satire Classic Quote: “What are those Negroes doing in first class?”

Nothing too heavy-handed here. Just a reminder that whether you are Middle Eastern, Black, White, Native American, or buffalo, we’re all united assholes.

63. O’Dweeds (2003)
Aired: Season 1, Episode 12 Headliners: Dave Chappelle, Sophina Brown, Irma St. Paule, Phyllis Somerville, Duane Littles, Barney Fitzpatrick Genre: Commercial parody Classic Quote: “So it’s like O’Douls, but for weed.”

When Dave delivers a shotgun blast of weed smoke to a baby’s face, you can hear the studio audience break out in a collective howl. But don’t worry, implores the commercial: O’Dweeds is the first brand of marijuana with no THC.

62. The Real Side of Gary Coleman (2006)

Aired: Season 3, Episode 2
Headliners: Dave Chappelle, Crystal Cotton, Isiah Whitlock Jr. Genre: Situation comedy Classic Quote: “What you talkin’ ’bout, bitch?”

There’s always a danger of satirizing a real-life insane incident like the late Gary Coleman’s 1998 attack on a fan asking for an autograph. How do you top the four-foot-seven former child star turned mall security guard punching a woman for allegedly mocking his flatlining career? You get Dave to play Coleman, turn the tussle into a howling store brawl, and flip one of television’s most recognizable catchphrases into an off-color punch line.

61. Dave Gets Revenge (2006)

Aired: Season 3, Episode 1
Headliners: Dave Chappelle, Spike Lee Genre: Situation comedy Classic Quote: “I don’t know about you, but I want some doughnuts!”

In this three-parter, Dave has a list of all the people who have done him wrong. He gets back at an old flame who cheated on him by tricking her into leaving her husband and starting a new life with him. He ruins the career of a casting agent who said he would never make it, recruiting Oscar-winning director Spike Lee to lie about the woman using the N-word while filming Jungle Fever. And when he finds the wheelchair-bound man who once banned him from a comedy club, he pushes the poor bastard down the stairs and then burns the spot down. Note to self: Don’t piss off Dave.

60. Dave Has $55 Million (2006)

Aired: Season 3, Episode 1
Headliners: Dave Chappelle, Vernon Campbell Genre: Situation comedy Classic Quote: “How you gonna get $25 million out of me if I got a nigga from Green Mile sitting on me in the middle of K Street?”

Mo’ money, mo’ problems. With his new $55 million deal from Comedy Central, Dave finds out what it means to be a wanted man. A St. Thomas barber charges him $11,000 for a haircut. The man at the car wash demands $900 for his services. Uncle Sam snatches up $25 million. Though no one knew at the time that Dave was going through a serious life crisis over the direction of the show, this sketch gives some crucial insight into his state of mind.

59. Ribs Sleep-Aid (2004)

Aired: Season 2, Episode 3
Headliner: Dave Chappelle Genre: Commercial parody Classic Quote: “Got that itis!”

Who needs sleeping pills when you have a bottle of barbecue ribs to knock you out?

58. Pretty White Girl Sings Dave’s Thoughts (2003)

Aired: Season 1, Episode 2
Headliners: Dave Chappelle, Erin Hill Genre: Musical spoof Classic Quote: “The police never looked for Tupac and Biggie’s murderers. Fuck the police.”

Dave has a few controversial things to get off his chest. So he decides to get a classically trained vocalist to sing some of his deepest, conspiratorial thoughts — like crack cocaine and AIDS being intentionally created to destroy the Black community. Watching a pristine White woman melodically belting out dead serious subject: That’s it, that’s the joke.

57. A Moment in the Life of Lil Jon: Oprah (2004)

Aired: Season 2, Episode 13
Headliners: Dave Chappelle, Lil Jon Genre: Situation comedy Classic Quote: “Ah skeet, skeet, skeet, skeet!!!”

Finally, Dave’s Lil Jon meets the real thing. It gets even more surreal when Oprah Winfrey calls in to tell the King of Crunk that she’s pregnant with his baby, a callback to a gag from a previous sketch.

56. Pitches, Man, Pitches (2004)

Aired: Season 2, Episode 9
Headliners: Dave Chappelle, Arsenio Hall Genre: Situation comedy Classic Quote: “Damn, this some good-ass cheese!”

Poor Dave. The man can’t even go out on a romantic dinner date without some a-hole pitching him a movie idea. But suddenly we’re transported inside Dave’s random thoughts, which sets up some hilarious scenarios: late-night talk show icon Arsenio Hall beating up White partygoers for not telling him how good the cheese is, and Dave as a rapping satyr. Yes, really.

55. Dave on ‘MTV Cribs’ (2006)

Aired: Season 3, Episode 3
Headliner: Dave Chappelle Genre: TV parody Classic Quote: “Come on in, you broke motherfuckers.”

In this “Lost Episodes” send-up of MTV Cribs, Dave flexes plenty of ludicrous immaculate consumption, including a marble foyer cut out from Space Mountain, a fur coat made from white pandas, his own sneaker-making sweatshop, and two tyrannosaurus eggs. There’s also some pointed shade at the Ying Yang Twins’ 2004 appearance on the balling-obsessed series.

54. ‘Roots’ Outtakes (2003)

Aired: Season 1, Episode 3
Headliner: Dave Chappelle Genre: TV spoof Classic Quote: “I told y’all not to give me a real baby. Pissing all over me.”

A blooper reel is the last thing you would expect from the 25th anniversary DVD commemorative edition of the groundbreaking ’70s miniseries Roots. But Chappelle pulls it off. Trust: You’ll never watch the “Kunta Kinte gets whipped” scene the same way again.

53. Blackzilla (2003)

Aired: Season 1, Episode 9
Headliner: Dave Chappelle Genre: Movie spoof Classic Quote: “That’s no snake, honey.”

There’s nothing particularly risk-taking or thought-provoking about an enormous Chappelle kicking Godzilla’s ass in Tokyo. In fact, Blackzilla can be viewed as culturally insensitive (cue Japanese townspeople scurrying about). And still the laughs can’t be denied. Dave makes a bong out of a smokestack and literally smokes some trees; pulls out his massive junk for a brief piss, much to the utter astonishment of onlookers; and has sex with a volcano. Sometimes abject silliness wins.

52. Dave Meets Show Business (2006)

Aired: Season 3, Episode 3
Headliners: Dave Chappelle, Lee R. Sellars Genre: Situation comedy Classic Quote: “Everyone gets nervous the first time they meet Show Business — except P. Diddy.”

Dave meets the grand and powerful avatar of show business (Sellars) who asks him what his career goals are. A kids’ cereal named after him, maybe? “I don’t know… thinking maybe I’d stay true to myself, you know, speak my mind,” Dave responds. Show Business lets out an ominous laugh. “TV Guide was right,” he says. “You are the funniest man on television!” Like many of the Season 3 sketches, “Dave Meets Show Business” acts as a window to his internal battle, struggling to keep his soul intact amid the whirlwind of his newfound celebrity. Deep.

51. The Time Haters (2004)

Aired: Season 2, Episode 11
Headliners: Dave Chappelle, Donnell Rawlings, Yoshio Mita, Charlie Murphy Genre: Situation comedy Classic Quote: “We’ve traveled all the way back from time to call you a cracker.”

The “Playa Haters’ Ball” crew uses a time machine to diss Hitler and kill a slave owner. When he finally showed the sketch on the “Greatest Misses” episode, Dave admitted that the fact that the sketch was kept under wraps for so long was baffling. “Apparently shooting a slave master isn’t funny to anybody but me and Neal,” he joked. “If I could, I’d do it every episode.”

50. Negrodamus (2004)

Aired: Season 2, Episode 5
Headliner: Paul Mooney Genre: TV parody Classic Quote: “White people love Wayne Brady because he makes Bryant Gumble look like Malcolm X.”

With any good Chappelle’s Show piece, there are layers to the jokes and narratives that stretch through multiple episodes. After Mooney was asked why White folks are such big fans of amiable TV host Brady, his mocking answer would later become the foundation for one of the series’ most celebrated sketches.

49. Giving Up the Show (2004)

Aired: Season 2, Episode 12
Headliners: Dave Chappelle, Big Boi, Nick Cannon Genre: Situation comedy Classic Quote: “Nothing makes me happier than to be able to take another Black actor’s job.”

After Dave complains to Comedy Central that he’s burnt out from the frantic pace and threatens to quit, network execs call Dave’s bluff: “At this point in the season, you’re replaceable.” All’s well and good, until Dave sees Wayne Brady hosting his show. Distraught, he calls OutKast’s Big Boi, who blows him off (“We playing [tennis] on the moon, bitch, peace!”). To add insult to injury, Dave later bumps into his own son hanging out with Nick Cannon — delivering on a premise teased nine episodes earlier.

48. Ask a Black Dude: Walking (2003)

Aired: Season 1, Episode 5
Headliner: Paul Mooney Genre: Q&A Classic Quote: “Yeah, Black people can jump high. You gotta jump. You gotta do something when you are running from the police.”

Mooney returns for more politically incorrect (and low-key racist) questions like: Can all Black dudes jump high? Why do they walk with a swag? And why do Black folks like to smoke weed? In usual fashion, the unfiltered funnyman’s answers anchor a skit that could have easily gone sideways. Keep your eyes peeled for a weird cameo from Twisted Sister’s Dee Snider.

47. Black Monsters (2006)

Aired: Season 3, Episode 3
Headliners: Charlie Murphy, Donnell Rawlings, Dave Chappelle Genre: TV parody Classic Quote: “Nigga, you a Frankenstein.”

With some more polishing, this eight-minute nod to ’60s sitcom The Munsters could have been a top 10 sketch. Horror icons Frankenstein (Murphy), Wolfman, and the Mummy (Rawlings) are living under the same roof as they go through life’s everyday struggles. When Frankenstein is fired by his boss for his “lack of conflict resolution,” he goes ballistic and smashes up the office. In his mind, he’s being discriminated against not because he’s Frankenstein—a raging, violent monster—because he’s Black. Unfulfilled comic brilliance.

46. Car Dancing Commercial (2003)

Aired: Season 1, Episode 1
Headliners: Dave Chappelle, Erin Stutland Genre: Commercial parody Classic Quote: “All that crazy dancing was making my penis go soft.”

Chappelle’s Show’s very first sketch to air sets the tone for all that would follow. The two-fisted spoof takes aim at a 2003 Mitsubishi 3G Eclipse ad, which featured a White woman spastically pop locking inside a car. In Dave’s version, he says what was all on our minds: What the hell is wrong with this chick? Chappelle promptly kicks her out of the whip and invites in an attractive Black woman to show off some more around-the-way moves. “That is what I call dancing,” Chappelle says. “You should have seen the girl who was sitting here before you!”

45. Ask a Black Dude: Dentists (2003)

Aired: Season 1, Episode 7
Headliner: Paul Mooney Genre: Q&A Classic Quote: “I have a Stephen King horror movie: Nigger With a Brain. We’ll see how that scares people.”

This was the moment “Ask a Black Dude” hit its stride. Watching Mooney take on the evergreen question of why Black movie characters are often the first to get killed is riveting stuff. But seeing the fearless comic take on a perplexing question by horror master Stephen King is especially delicious.

44. Wu-Tang Financial (2003)

Aired: Season 1, Episode 7
Headliners: RZA, GZA Genre: Commercial parody Classic Quote: “You need to diversify your bonds, nigga.”

Of course you want the hip-hop crew that once declared “Cash Rules Everything Around Me” to help you invest your money. The RZA and the GZA are having so much fun, you almost wish the whole squad came along. Bong bong!

43. Samuel L. Jackson Beer (2004)

Aired: Season 2, Episode 1
Headliner: Dave Chappelle Genre: Commercial parody Classic Quote:Deep Blue Sea… they ate me! A fucking shark ate me!”

Again, it’s all in the details. A gag like “Samuel Adams, but with Samuel L. Jackson” only works if you embrace the lunacy of the sketch. It’s not enough to just do a bombastic impersonation of the actor. You have to place Chappelle in Jackson’s Jheri curl wig from Pulp Fiction, dress him up as Founding Father Samuel Adams, let the man run wild, and get out of the way.

42. I Know Black People (2004)

Aired: Season 2, Episode 8
Headliner: Dave Chappelle Genre: Game show Classic Quote: “A badonkadonk is like an incredibly attractive ass.”

Listen up, White folks: if you know what loosies are, why Black folks love menthol cigarettes, and what Good Times’ Mr. Bookman did for a living, then you’re good with us.

41. Redman Potty Fresh (and Redman’s Potty Fresh Reprise) (2003)

Aired: Season 1, Episode 5
Headliner: Redman Genre: Commercial parody Classic Quote: “Flush the toilet with yo’ pancake ass, bitch!”

As fake television ads go, “Redman Potty Fresh” — a clear shout-out to those ridiculous Ty-D-Bol commercials that ran from the late 1960’s to the ’80s — sticks the landing. Watching Reggie Noble on a jet ski inside a toilet bowl cursing out a White woman as he explains the product’s cleaning benefits (“Enzymes and shit collaborate together…”) is the kind of off-centered hijinks that gave Chappelle’s Show immediate counterculture appeal. SNL wasn’t going in this direction.

40. Tyrone Biggums’ Fear Factor (2004)

Aired: Season 2, Episode 12
Headliners: Dave Chappelle, Joe Rogan Genre: TV parody Classic Quote: “I’m gonna tell you something about me, Joe Rogan, that you might not know: I smoke rocks.”

Our list’s first appearance of everyone’s favorite crackhead, Tyrone Biggums, proves why he’s one of Chappelle’s Show’s most durable characters: You can place him in nearly any scenario with the comedy rewards being endless. Of course a hardened survivor like Tyrone would win a grossfest competition like Fear Factor. We could’ve done without the elk penis in a “light cream testicle sauce,” though.

39. Real Movies: ‘Deep Impact’ (2003)

Aired: Season 1, Episode 10
Headliner: Dave Chappelle Genre: Movie spoof Classic Quote: “I urinate on people when I have sex with them. I’m a disgusting human being, and I apologize to the people I’ve hurt and peed on.”

Chappelle jumps into the stoic role of Morgan Freeman’s President Tom Beck in the 1998 sci-fi disaster film Deep Impact. Beyond that, everything else is unhinged. Beck pushes back on the news that a giant asteroid on a collision course to destroy Earth is somehow the Black guy’s fault. He then curses out the press, unveils a cure for AIDS, offers up who killed Kennedy, admits to a golden showers fetish (although, again, the R. Kelly joke doesn’t hit quite the same in 2020), and makes his escape from impending doom on an alien spaceship. Word to Bibble.

38. WacArnold’s (2004)

Aired: Season 2, Episode 2
Headliners: Dave Chappelle, Charlie Murphy, Donnell Rawlings, N’Bushe Wright Genre: Commercial parody Classic Quote: “Uh, nigga, you smell like french fries.”

“Remember that commercial where that guy Calvin would get a job at a fast food restaurant, and they’d act like that’s the best thing in the ghetto, like the whole neighborhood’s excited?” Chappelle asks the studio audience, teeing up the spoof. But instead of the hood cheering on Calvin as he earns a check flipping burgers, he’s dissed by girls, gets robbed and ridiculed by stickup kids, and finds out that his baby’s mother is cheating on him because of his greasy job. Go Calvin!

37. The Dave Chappelle Story (2003)

Aired: Season 1, Episode 6
Headliner: Dave Chappelle Genre: Movie spoof Classic Quote: “Spaghetti, spaghetti, spaghetti, spaghetti, spaghetti!”

Dave writes and directs his own biopic. Just try to keep a straight face as you witness his shocking, laughably graphic birth. (Apparently Chappelle had a massive penis as a baby and was already a comedic genius.) There’s also a wacky 8 Mile spoof in which Dave prepares to do battle as a stand-up comedian.

36. ‘Law & Order’: Tron Carter (2004)

Aired: Season 2, Episode 5
Headliners: Jonathan Walker, Dave Chappelle, Bill Burr Genre: TV parody Classic Quote: “There are! I say there are so many amendments in the Constitution of the United States of Americaaaa! I can only choose one! I can only choose ooooooone! I plead the fif! I plead the fif! FIVE! 1,2,3,4, fiiiif!”

When Tron Carter, one of Chappelle’s Show’s most popular recurring characters, testifies in front of the Senate Subcommittee Hearing on Narcotics, the fun begins. In this upside-down version of Law & Order, the lovable crack-dealing rogue gets treated like a pillar of the community, while his White counterpart is framed and thrown in prison as if it were an afterthought. Scathing critique of systemic racism aside, Tron also proves that there are myriad ways to protect against self-incrimination.

35. AND1 Mixtape: Uncensored (2003)

Aired: Season 1, Episode 12
Headliners: Dave Chappelle, Donnell Rawlings Genre: Sports madness Classic Quote: “Yo, he’s the sickest motherfucker I ever seen in an alley, son!”

From the late 1990s to the mid ’00s, the AND1 Mixtape was the hottest street basketball video series on the planet. Players like Anthony “Half Man, Half Amazing” Heyward, Larry “Bone Collector” Williams, Grayson “The Professor” Boucher, and Troy “Escalade” Jackson became mainstream stars.

This is exactly why Chappelle’s twist on the skillful, flashy, dancing, trick-shot flexing league is so damn funny. Baseball, tennis, bowling — no sport is safe from AND1’s theatrics. Add an appearance from Karl Lake, Chappelle’s Show Dancing Robot Guy, and you’ve got an unhinged comedy explosion.

34. NBA Players (2003)

Aired: Season 1, Episode 12
Headliner: Charlie Murphy Genre: Sports madness Classic Quote: “Rasheed Wallace!”

Dave flips the idea of everyday basketball fans yelling the names of their favorite NBA star after making a big shot (“Kobe!”) into something much more farcical. Murphy screams out “Rasheed Wallace!” when he is busted for smoking weed; a man strangles his boss and proclaims “Sprewell!”; a dude having sex with multiple partners shouts “Wilt Chamberlain!” while a man dressed in women’s clothing responds “Dennis Rodman!” By the time Paul Pierce’s 2000 stabbing comes into the mix, it’s clear that Chappelle and crew gave no fucks.

33. When Keeping It Real Goes Wrong: Darius James (2004)

Aired: Season 2, Episode 6
Headliners: Dave Chappelle, Toni Townsend, Donnell Rawlings, Martha Elliott Genre: TV parody Classic Quote: “Unlike you, I’m getting a little action tonight, you punk bitch.”

The very first installment of “When Keeping It Real Goes Wrong” starts things off with a proverbial bang. Chappelle’s Darius Jones is suckered into a fight by a man who happens to hold a 10th-degree black belt. Not only does dude kick his ass, but Darius’ woman joins in on the excessive pummeling of an obvious dummy dressed as Dave that’s so hysterical it will leave you gasping for air.

32. Celebrity Trial Jury Selection (2004)

Aired: Season 2, Episode 9
Headliners: Dave Chappelle, Neal Brennan, Charlie Murphy Genre: Situation comedy Classic Quote: “He made Thriller…”

Dave goes in for jury selection, where he is asked to weigh in on the cases of high-profile Black celebrities Michael Jackson, O.J. Simpson, and R. Kelly (more on dude later). His theories are illogical, to say the least (“Some people say that cucumbers taste better pickled…”). But it’s not like Dave wholeheartedly believes in their innocence; he just believes that the Black community has for decades been given a raw deal by a racist legal system. It’s a message made clear when he’s asked about actor turned murderer Robert Blake: “Oh, yeah, Beretta did that shit.”

31. Zapped (2003)

Aired: Season 1, Episode 3
Headliner: Dave Chappelle Genre: TV parody Classic Quote: “Y’all been Zapped!”

While Chappelle’s Show has achieved landmark status, it’s also a phenomenon of its time. So you should expect a few you-had-to-be-there references, like this satirical jab at prank shows like Ashton Kutcher’s Punk’d and Jamie Kennedy’s The Jamie Kennedy Experiment. Unlike the originals, the pranks here are downright menacing. The worst? Dave dresses up as a hospital surgeon and tricks children into believing that their parents have just died. It’s even funnier when the two kids’ smiling mom and dad appear from out of nowhere. Dave also ends the skit with a slam at the now-defunct WB Network and its minstrel-inspired cartoon mascot, Michigan J. Frog, who appears on Dave’s shoulder and belts out “Mammy!” Yikes.

30. It’s a Wonderful Chest (2003)

Aired: Season 1, Episode 3
Headliners: Dave Chappelle, Liz Beckham Genre: Situation comedy Classic Quote: “You know what you need? A new set of titties and a boyfriend.”

On paper, “It’s a Wonderful Chest” reads like lazy, unimaginative frat-boy humor. Thankfully, the sketch as realized goes way beyond stale boob jokes. The well-endowed Sheila (Beckman) soon finds out there’s another set of rules for the beautiful ones. With Dave as her It’s a Wonderful Life–ish guide, she discovers that without her prodigious breasts she’s treated like an afterthought — not just by men, but her girlfriends, too.

29. PopCopy (2003)

Aired: Season 1, Episode 1
Headliners: Dave Chappelle, Guillermo Diaz, Michael Rapaport, Dominique Witten Genre: Situation comedy Classic Quote: “Cuz fuck ’em, that’s why.”

It’s obvious from its employee training film that PopCopy offers the worst customer service in human existence. A way-too-upbeat manager (Chappelle) takes would-be workers through the ins and outs of how to frustrate, confuse, insult, and scare customers — all with a shit-eating smile. One of the earliest ideas Dave and Neil pitched to Comedy Central, this sketch delivers, all the way down to Diaz admitting his toe-sucking fetish in front of horrified patrons.

28. Tupac Is Still Alive (2006)

Aired: Season 3, Episode 1
Headliners: Dave Chappelle, Questlove Genre: Musical spoof Classic Quote: “I wrote this song a long time ago, feel me!”

The Roots bandleader Questlove plays the latest posthumous Tupac record. But when Makaveli starts rapping about events that took place after his 1996 death, describes partygoers inside the club (“There’s a pudding stain on the back. What the fuck is that? It might be doo-doo!”), and calls out Dave for dancing with a woman who’s not his wife, things take a laughably wild turn.

27. Better in Slow Motion (2004)

Aired: Season 2, Episode 1
Headliners: Dave Chappelle, Andrea Lin, Gloria Velez Genre: Situation comedy Classic Quote: None

According to Dave, everything is better in slow motion. That includes such mundane tasks as laundry, walking through a crowded club, and fighting as iconic music video model Gloria Velez indulges in some girl-on-girl action. (I’m sensing a theme from Chappelle.) What’s not cool in slow motion: Dave taking a shit.

26. Make-A-Wish (2003)

Aired: Season 1, Episode 11
Headliners: Dave Chappelle, Nancy Ringham, Nolan Tuffy Genre: Situation comedy Classic Quote: “Nurse… can you come in here quickly? Billy is getting his ass whooped on Street Hoops!”

So, how do you get away with having Dave Chappelle mock a terminally ill kid while beating him in a video game? You toss off a seemingly throwaway line about young Billy being a fan of Half Baked and then let the jokes fly. “Nigga, you play like a bitch!” he taunts Billy as he clings on for dear life. Dave loves the kids.

25. Trading Spouses (2003)

Aired: Season 1, Episode 12
Headliners: Karyn Quackenbush, Dave Chappelle, Tina Benko, Melle Powers, Jelani Jeffries Genre: TV parody Classic Quote: “I learned that White people don’t use washcloths.”

The no-nonsense, cigarette-dangling Leonard Washington and perpetually square (and White) Todd Jacobson (both played by Chappelle) wife-swap in this direct jack of the reality TV series Trading Spouses. What could go wrong? Plenty. Todd introduces the Washingtons to parsnips, Leonard disciplines the Jacobson’s durag-wearing G-Unit superfan son (“G G G G get yo ass in the car!”) by dropping him off in the hood, and jokes about “titty residue” abound. Perfect.

24. White People Can’t Dance (2004)

Aired: Season 2, Episode 3
Headliners: Dave Chappelle, Questlove, John Mayer, Karl Lake Genre: Situation comedy Classic Quote: “Oops pow surprise!”

Another simple sketch that finds Chappelle playing deftly with racial stereotypes. This time out, Dave wants to obliterate the notion that White people can’t dance. “It’s just that they like certain musical instruments,” he explains. To test his theory, he recruits guitar hero Jon Mayer. When the rock star plays some Grateful Dead–style licks and metal runs on electric guitar in a corporate office and an upscale restaurant, White folks lose their minds — yet when he does the same in a Harlem barbershop, he’s completely shut down. Thankfully, Questlove gets the party started, prompting a joyous, daft appearance by the Robot Guy and a head-scratching freestyle from an extra. An electric piano ignites Latinos to salsa dance. The kicker: Dave and Jon spot a Black police officer singing and dancing along to Poison’s arena ballad “Every Rose Has Its Thorn.” “I’m from the suburbs, man,” the cop says. “I can’t help it.”

23. Tyrone Biggums: Red Balls Energy Drink (2004)

Aired: Season 2, Episode 5
Headliner: Dave Chappelle Genre: TV parody Classic Quote: None

When Biggums ingests cocaine in a can, he becomes a superhuman crackhead — sprinting to smash a car window, lifting up a bus. But his heroic deeds are never quite what you expect. Who needs Red Bull?

22. Fisticuffs (2003)

Aired: Season 1, Episode 11
Headliners: Dave Chappelle, Funkmaster Flex, Donnell Rawlings, Big Tigger Genre: Musical spoof Classic Quote: “Turn my headphones up!”

Fisticuffs may just be the greatest rapper to ever hit the booth. Or he would be, if he could ever manage to get a pair of decent headphones and finish a track.

21. Jedi Sex Scandal (2003)

Aired: Season 1, Episode 7
Headliner: Dave Chappelle Genre: Fake news Classic Quote: “Yes, they deserve to die, and I hope they burn in hell!”

Over the last decade, a string of sex abuse scandals have rocked the worlds of politics, religious institutions, the news media, and music industry. But what if there were such career-ending scandals in the Star Wars universe? Chappelle’s lamest news anchor, Chuck Taylor, delivers an explosive exposé on the Jedi who have systematically molested young Jedi Knights.

The embattled head of the Jedi Council, Yoda (Dave), resigns during a press conference after a video surfaces of him touching Jedi Boys and snorting coke. It’s chuckle-worthy for sure, but again, Chappelle stumbles into old stereotypes of portraying gay characters as effeminate sexual predators. The premise gets back on track and goes meta when Mace Windu (another Dave sighting!) rebukes Yoda, looking and sounding conspicuously like the Samuel L. Jackson Beer pitchman.

20. Kneehigh Park (2004)

Aired: Season 2, Episode 10
Headliners: Dave Chappelle, Q-Tip, Charlie Murphy, Snoop Dogg, Randy Pearlstein Genre: TV parody Classic Quote: “You don’t understand/Cuz I make love to my hand/So I don’t need you honey/I beat my dick like it owes me money/Fuck it.”

If you’re looking for Sesame Street, this ain’t it. This is a twisted children’s show where foulmouthed puppets like Dangle (voiced hilariously by Snoop Dogg) sing profane songs about STDs and drugs. But the MVP here is Charlie Murphy as Stinky, an obvious nod to Oscar the Grouch who has no chill around children.

19. Black Bush (2004)

Aired: Season 2, Episode 13
Headliners: Dave Chappelle, Donnell Rawlings, Jamie Foxx, Mos Def, Anthony Berry Genre: Political satire Classic Quote: “The cradle of fucking civilization!”

What if President George W. Bush were Black? In this pre-Obama sketch, it’s a simple, unspectacular idea — but in the hands of Chappelle and crew, it soars. At the center is the Bush administration’s contentious run-up to the 2003 invasion of Iraq. And there’s not a weak link in this sketch. Chappelle as W. conveys just how shady the claims of Saddam Hussein having WMDs truly were. Rawlings and Holler Man both deliver killer ad libs. Guest star Jamie Foxx gamely sinks his teeth into U.K. Prime Minister Tony Blair. And Mos Def’s hooded-out head of the CIA claims that Iraq has yellow cake uranium but shows actual yellow cake as proof.

18. When Keeping It Real Goes Wrong (2004)

Aired: Season 2, Episode 8
Headliner: Quincy Tyler Bernstine Genre: TV parody Classic Quote: “I don’t like people playing on my phone.”

The only “When Keeping It Real Goes Wrong” not to feature Dave Chappelle, this installment still ranks as the best. Much of the credit goes to the talented Quincy Tyler Bernstine, who plays the beyond irrational Brenda Johnson. After a woman mistakenly calls her home, Brenda goes code red with suspicions that her boyfriend is cheating: “I’m finta ride on this bitch!” Brenda does just that and finds herself in a federal prison, where she catches a hilarious beatdown for — wait for it — keeping it real.

17. Profiles in Courage: Toilet Pioneer (2004)

Aired: Season 2, Episode 13
Headliners: Dave Chappelle, Charlie Murphy Genre: Mockumentary Classic Quote: “So, little did I know that roast beef sandwich would change my life forever.”

The 1950s’ Montgomery bus boycott and Brown v. Board of Education set the stage for the civil rights movement. But did you know about Cyrus Holloway’s courageous fight against segregation? We won’t ruin the bathroom humor, but suffice it to say it’s a careful tightrope act that keeps its balance between reverence and brazen silliness. Bravo.

16. Tyrone Biggums’ Classroom Visit (2003)

Aired: Season 1, Episode 2
Headliners: Dave Chappelle, Susan Greenhill Genre: TV parody Classic Quote: “That, children, was the first time I sucked a dick for crack.”

When Tyrone Biggums is invited to speak to schoolkids about the evils of drugs, it goes about as well as you’d imagine. Not only is it a violation of his parole to be around children, but Tyrone’s idea of a substance-prevention talk is glorifying the joys of laced weed and acid, giving directions to his go-to crack dealer, and taking a shit in a wastebasket in front of scarred-for-life students.

15. Oprah’s Baby Daddy (2004)

Aired: Season 2, Episode 9
Headliners: Dave Chappelle, Kadene Kerr, Yoshio Mita Genre: Situation comedy Classic Quote: “Gotcha, bitch!”

Dave thinks he’s hit the lottery when America’s beloved billionaire media mogul Oprah Winfrey tells him she’s pregnant with his child. He quits Chappelle’s Show, tells the staff to kiss his ass, and trashes the office. He even buys a king’s crown and takes martial arts lessons from Bruce Lee’s brother (Mita). It’s a maniacal romp steadied by the uncanny, matter-of-fact voice work of Kerr as Oprah.

14. The World Series of Dice (2004)

Aired: Season 2, Episode 7
Headliners: Dave Chappelle, Donnell Rawlings, Eddie Griffin, Charlie Murphy, Yoshio Mita, Bill Burr, Robert Petkoff Genre: Sports madness Classic Quote: “I’m Leonard Washington… I don’t get buck naked for nobody.”

Judging from the immense popularity of Rawlings’ Ashy Larry, you would have thought the lotion-averse hustler appeared in a plethora of Chappelle’s Show sketches. That speaks to not only the underrated talent of the Washington, D.C., native and the infectious draw of his breakout character, but also the in-the-zone excellence of the entire sketch.

Griffin’s Grits ’n Gravy effortlessly rolls scene-stealing one-liners, Burr and Petkoff make color commentary sound straight-up grimy, and Trading Spouses’ Leonard Washington getting shot in the kneecap by Marcy Projects stickup kid Quills (Murphy) while in the middle of a soaring speech never get old.

13. World’s Greatest Wars (2003)

Aired: Season 1, Episode 10
Headliners: Ed Fry, Dave Chappelle, Mos Def Genre: Mockumentary Classic Quote: “It’s called crack. It’s great. And it’s so simple to make. All you need is cocaine and some baking soda, and I think I tasted egg and cinnamon.”

War reenactments have long been a staple on the History Channel. Chappelle’s Show borrows from that documentary genre for another satirical dramatization—the evolution of the 1980s crack wars involving the Chicago’s faux 19th Street Gangsters and the River Terrace Crew—and the foolishness never lets up. There’s a ludicrous corner-store fight between rival gang leaders Earl “The Snake” White (Chappelle) and General Cornrow Wallace (Mos Def). And Tyrone Biggums pops up to put Cornrow on to a new drug called crack, prompting the most illiterate letter ever written (“Yall nigars kneed to Kook up kokane wif baking soda and sell it…”). Ppprrrrr.

12. Tyrone Biggums’ Crack Intervention (2003)

Aired: Season 1, Episode 8
Headliners: Dave Chappelle, Isiah Whitlock Jr., Patrick Collins, Cherene Snow, Remy K. Selma Genre: TV parody Classic Quote: “Is this the 5:00 free crack giveaway?”

Tyrone’s family and friends trick him into coming to an intervention by luring him with a flyer for a “Free Crack Giveaway.” They share stories about how he has deeply hurt them, running the gamut from stealing his sister’s car to selling the home of a couple who took him in after they gave him money to pursue his real estate agent’s license. Tyrone being Tyrone, his promise to get clean and go to rehab is a sham. He makes his escape by flushing himself down the toilet! Peak T.B. (“Tyrone Biggums,” not “toilet bowl.’)

11. ‘Frontline’: Racist Hollywood Animals (2003)

Aired: Season 1, Episode 8
Headliners: William Bogert, Dave Chappelle, Donnell Rawlings, Mos Def, Rita Frazier, Melle Powers Genre: Mockumentary Classic Quote: “It’s James… the nigger-hating dolphin!”

Frontline host Kent Wallace uncovers the long, dark, racist history of America’s most beloved celebrity animals. The writing here is particularly sharp. We hear firsthand testimony of supposedly Rin Tin Tin attacking African American protesters at civil rights marches. (“I saw the show… I saw the dog. I said, where do I know this dog from?” recalls security guard Justin Wilkes (Chappelle), who claims he was bitten by the hateful canine. “And it hit me. Selma, Alabama… 1957 riot in front of Woolworths!”) There’s even a fake outtake from Mr. Ed showing the talking horse using the N-word toward a black co-star. And Mos Def turns in a master class in deadpan delivery as a man victimized by bigoted bottlenose dolphin Flipper, aka James.

10. ‘Making the Band’ (2004)

Aired: Season 2, Episode 10
Headliners: Dave Chappelle, Da Band, Wyclef Jean Genre: TV parody Classic Quote: “All right, the only way I’ll open the studio up now… y’all gotta walk uptown to the Bronx and get breast milk from a Cambodian immigrant. I only drink the finest breast milks.”

We kick off the best of the best with Making the Band, a bonkers version of Sean “P. Diddy” Combs’ already over-the-top ’00s reality show competition. Sure, some of the dated jokes will undoubtedly go over younger heads who have never seen the MTV series. You won’t get the backstory behind Ness and Chopper’s incessant fights in the studio. Or Diddy making Babs, Sara Stokes, and the rest of his Da Band protégés walk all the way from Midtown Manhattan to northern New Jersey to buy a set of left-handed golf clubs (on an actual show, Combs instructs the group to walk to Brooklyn to buy a slice of Junior’s Cheesecake on a whim).

But you will get Chappelle in top form, portraying the hip-hop mogul as a laughably ostentatious taskmaster so overly indulged that he has to be carried around by his bodyguards. It’s a clever nonsensical touch made all the more impressive when juxtaposed with Chappelle’s imitation of the perpetually confused Dylan (“I spit hot fire!”).

9. Reparations 2003 (2003)

Aired: Season 1, Episode 4
Headliners: Dave Chappelle, Donnell Rawlings Genre: Fake news Classic Quote: “I’m rich, biaaatch!”

African Americans finally get their reparations for slavery. Chappelle pulls double duty as the whitefaced Chuck Taylor, who can’t hide his disdain for the new developments, and as Tron, everyone’s favorite street hustler turned richest person in the world. (Of course the Chappelle’s Show regular increases his reparations money in a dice game.)

Two million delinquent phone bills are paid off. Gold is way up on the commodity trading market. Chicken explodes to $600 a bucket. Eight thousand record labels are started within an hour as FUBU becomes the world’s largest corporation merging with Kentucky Fried Chicken, prompting the end to the recession.

But beyond the flying stereotypes is a serious message. When Taylor asks why there aren’t any banks in Black neighborhoods, the news reporter answers, “Well, Chuck, that’s because banks hate Black people. But I think that’s about to change.” And when Rawlings appears in a truck after buying a lifetime supply of cigarettes, delivering one of Chappelle’s Show’s most memorable lines — “I’m rich, biaaatch!” — the sketch attains mythical status.

8. The Mad Real World (2003)

Aired: Season 1, Episode 6
Headliners: Dave Chappelle, Charlie Murphy, Christian Finnegan, Tiffany Thompson, Jenn Perkins Stephens, Patrick Garner, Amy Garber, Craig “MuMs” Grant Genre: TV parody Classic Quote: “Be careful if you get a sleeper hold. Because the next day your anus will really hurt.”

In the DVD commentary for Chappelle’s Show Season 1, Chappelle recalls the time he helped friend and stand-up comedian David Edwards score a part on the influential reality series The Real World. Edwards’ headline-making 1993 eviction from the show and the marginalization of other Black cast members inspired Chappelle to come up with a parody of the MTV staple.

From the start, “The Mad Real World” makes its reverse-engineering agenda clear. Chad (Christian Finnegan), the conspicuous, bossy White guy, is placed in the same house with six rebellious Black folks. “He didn’t know what he was getting himself into,” says one of the roommates. That’s putting it mildly.

Chad ends up bunking in the same room with ex-con Tyree (Murphy at his best), who takes Polaroid pictures of himself and his boy Lysol (poet and Oz actor muMs) having a three-way with his perky girlfriend Katie. Chappelle’s Tron uses a wrestling hold and knocks Chad out, at which point he’s robbed and apparently sexually assaulted. And when Chad’s father comes by for a visit, Tyree stabs him. Fun times.

7. The Playa Hater’s Ball (2003)

Aired: Season 1, Episode 9
Headliners: Dave Chappelle, Ice-T, Donnell Rawlings, Charlie Murphy, Patrice O’Neal, Yoshio Mita, Troi “Starr” Torain Genre: Mockumentary Classic Quote: “Very insulting what you said about my coat. It’s made out of your mother’s pubic hair.”

A perfect satire is all in the details — and there’s no shortage of them in this unruly sendup of HBO’s 1998 documentary Pimps Up, Ho’s Down. But instead of a glimpse inside the dangerous pimping lifestyle and underground awards gala the Players’ Ball, we get a front-row seat to the 9th Annual Player Hater’s Ball. “Real hating, man, that’s like an art form,” says Ice-T, who plays the resentful emcee of the event (and who actually made an appearance in Pimps Up).

Chappelle’s Silky Johnson is easily in the running for one of the series’ most hysterical characters. Just watch him exchange glorious insults with Murphy (Buc Nasty), Rawlings (Beautiful), and the late Patrice O’Neal (Pit Bull). Among the best of the verbal takedowns: “Man, you outta take that cane and beat whoever made that suit to death.” The sketch even gives Yoshio Mita some shine in a sketch that boasts an embarrassment of comedic riches.

6. The Niggar Family (2004)

Aired: Season 2, Episode 2
Headliners: Dave Chappelle, Dan Ziskie, Margo Skinner, Johnny Pruitt, Sophina Brown Genre: TV parody Classic Quote: “Oh Lord, this racism is killing me inside.”

href="http://www.cc.com/video-clips/mlg0y7/chappelle-s-show-the-niggar-family---uncensored">A fearless sketch that likely wouldn’t make it past squeamish basic cable censors today. Sure, the idea of a White family being named after the N-word comes off as a play for shock value — but the black-and-white ’50s sitcom spoof goes much deeper. Here “er” is changed into “ar,” as if the writers are giving us a coy wink. But what we actually hear is a hard ER. When Mr. Frank Niggar shows off a picture of his sister’s newborn baby, his wife, Emily, observes, “She’s got those Niggar lips!”

It’s a powerful pretext that’s pushed even further when neighborhood milkman Clifton (Chappelle doing a killer Eddie “Rochester” Anderson impersonation) stops by to collect on a past delivery. “I know how forgetful you Niggars are when it comes to paying bills,” he says as a cheesy laugh track plays. The sketch turns dark, of course, from a restaurant reservation mix-up to a third-wall-breaking capper — but through it all, it’s as discomfiting as it is dynamite.

5. The Wayne Brady Show (2004)

Aired: Season 2, Episode 12
Headliners: Dave Chappelle, Wayne Brady, Donnell Rawlings, Deanna George Genre: Situation comedy Classic Quote: “Is Wayne Brady gonna have to choke a bitch?”

Brady’s saccharine family-friendly image serves as the foundation for a brilliant comedic pop culture experiment when Dave meets up with the omnipresent singer, actor, and game show host to hang out. All is well until Brady goes gangsta and commits a drive-by shooting, inexplicably killing a man (Rawlings). The pimping, murderous sociopath collects money from his stable of girls, threatens one of the women for coming up short (“Is Wayne Brady gonna have to choke a bitch?”), and forces Dave to smoke weed laced with PCP. Suddenly Brady’s attentions are clear: It’s all payback for a previous joke Paul Mooney made at his expense in a “Negrodamus” sketch.

4. The Racial Draft (2004)

Aired: Season 2, Episode 1
Headliners: Dave Chappelle, Mos Def, Angie Martinez, Henry Yuk, Ed Rubeo, RZA, Bill Burr, Randy Pearlstein Genre: Situation comedy Classic Quote: “He’s been discriminated against in his time, he’s had death threats, and he dates a White woman. Sounds like a Black guy to me.”

“The Racial Draft” excels because it never forgets that we’re all in on the joke. Its brilliant use of a mock draft allows viewers to ponder just what would happen if we had the power to pick and trade some of our favorite (and non-favorite) entertainers and professional athletes. The Black delegation’s first pick is Tiger Woods (a cheesing Chappelle), initiating a litany of racial land mines. The Jewish delegation drafts Lenny Kravitz. The leader of the Latino delegation (Martinez) picks Elian Gonzales, the young boy who was at the center of an international custody dispute between Cuba and the United States. (“We wanted to do that,” she says, “before the White people try to adopt him as one of their own… again.”) The Whites choose General Colin Powell, keep Eminem, and give O.J. Simpson back to the Black delegation. By the time the Wu-Tang Clan is drafted by the Asian delegation, a classic is born.

3. Charlie Murphy’s True Hollywood Stories: Prince (2004)

Aired: Season 2, Episode 5
Headliners: Charlie Murphy, Dave Chappelle, Donnell Rawlings Genre: Musical spoof Classic Quote: “Game, blouses.”

Following the riotous reaction to Murphy’s story about Rick James (more on that in a moment), Chappelle’s Show takes us back to the time he was beaten in a game of pickup basketball by the Purple One himself. At the time, most viewers had no idea that the diminutive, high-heel-wearing music deity played hoops at Minneapolis’ Bryant Junior High. And judging from Murphy’s telling, the late superstar had handles.

It’s all there: a Jheri-curled Charlie; his brother Eddie and the crew laughing uncontrollably at the thought of matching up against Chappelle’s impersonation of an off-the-wall Prince and his androgynous clique (“You know where you got that shirt from… and it damn sure wasn’t the man’s department”). Mr. Nelson responds by crossing over fools on the court and running plays with obvious names like “Computer Blue” and “Darling Picky.” Prince even serves pancakes after the game. (Again, a true story.) No one who wasn’t really there will ever know if he actually humped a basketball or made a spectacular dunk — but hey, this is Prince we’re talking about. Anything is possible.

2. Charlie Murphy’s True Hollywood Stories: Rick James (2004)

Aired: Season 2, Episode 4
Headliners: Charlie Murphy, Dave Chappelle Genre: Musical spoof Classic Quote: “I’m Rick James, bitch!”

Before Chappelle’s Show’s now-legendary Rick James skit, Charlie Murphy was known as Eddie Murphy’s big brother (and Gusto from CB4). But after this sketch premiered and hipped viewers to the debauched, habitually line-stepping exploits of the king of punk funk — portrayed in flashbacks by Chappelle — Charlie became a household name.

Murphy’s real-life tales of hanging out with James and seeing his orange aura, only to be smacked by the Superfreak seconds later, is just one of many hilarious gags that seem to never end. The real-life Rick James (“Cocaine is a hell of a drug”) offers his admittedly hazy memories of his run-ins with the Murphy brothers. When Charlie describes kicking the out-of-control music superstar into a wall mirror (kudos to the stunt coordinator), James’ reaction will reduce you to tears. “I’m Rick James, bitch” became Chappelle’s Show’s signature catchphrase, James himself enjoyed a revitalized career before his death later that year, and Murphy became an in-demand comedian in his own right. Thank you, Charlie.

1. ‘Frontline’: Clayton Bigsby (2003)

Aired: Season 1, Episode 1
Headliners: Dave Chappelle, William Bogert Genre: Situation comedy Classic Quote: “I’m going to make this clear. I am in no way, shape, or form involved in any niggerdom. You understand!?”

This is the sketch that solidified Dave Chappelle’s comedic genius. In fact, it’s not hyperbole to say that the premiere episode sketch became a watershed cultural moment that transcended standard television comedy. Frontline host Kent Wallace introduces us to Bigsby, the world’s first Black White supremacist. It’s soon explained that the hatemonger, who was born blind, has been told all his life that he is White. “Sir, my message is simple,” Bigsby explains. “Niggers, Jews, homosexuals, Mexicans, Arabs, and all kinds of different chinks stink, and I hate ’em!”

The jump from there is breathtaking. Bigsby’s seething, hilarious hatred for especially Blacks (“They eat up all the chicken and think they are the best dancers!”) and his status as a successful author has made him a hero of White supremacists. But when he takes off his white Ku Klux Klan hood after giving a speech, audience members are horrified beyond belief — and beyond their skulls’ ability to contain their brains.

Looking back, it’s unforgivable that “Frontline: Clayton Bigsby” didn’t win an Emmy or a Golden Globe. It’s the kind of art that not only makes us laugh, but also makes us question the unreasonable lunacy that White supremacy represents. Bigsby has become so ingrained in our cultural memory that when an Black Alabaman named Daniel Sims went viral last month for supporting the Confederacy, it was impossible not to make the connection. GOAT.