Every Episode of ‘The Boondocks,’ Ranked
Credit: Sony Pictures Television

Every Episode of ‘The Boondocks,’ Ranked

Twenty-five years ago, Aaron McGruder introduced the world to the Freemans, and nothing would ever be the same

The Boondocks started out as a fallback plan.

Before creating the comic strip, Aaron McGruder was an aimless University of Maryland student who didn’t expect to graduate; instead, he wanted to be a comic book artist for Marvel. After realizing that his drawing skills weren’t up to par and that he’d lose his scholarship if he didn’t return to school, he’d loaded up on so many Afro American Studies courses that it was an obvious discipline to declare as his major. From there, he began to cultivate his defining work, one guided in part by his curriculum.

The Boondocks debuted on Hitlist.com on Feb. 8, 1996 before appearing in McGruder’s college newspaper, The Diamondback, later that same year. It eventually ran in The Source, too. The strip focused on the exploits of two elementary schoolers — a Black militant named Huey and his gangsta rap automaton little brother, Riley — and their grandfather, former Civil Rights era activist Robert Jebediah Freeman (affectionately known as Granddad). The three moved from the South Side of Chicago to the white-fenced fictional Woodcrest neighborhood after Robert decided he wanted to retire in peace, away from the dangers of the Chi. The only problem is that peace can be subjective, and assimilation, especially for Huey and Riley, can be even harder than it sounds.

When they first arrive in Woodcrest, Huey thinks he’s spotted late racist politician Bull Connor; it’s actually just a White guy washing his car. Riley is disgusted by the smell of the new town, but Huey tells him it’s just clean air. Their struggle to mesh with their new locale establishes the comedic fulcrum of the strip, one derived in part from the experiences of people like McGruder himself, who knew all too well “the intimidation of being one of two or three Black faces in a sea of faces that don’t look like you.”

With quippy one-liners and unfiltered commentary on race, rap, and American politics, The Boondocks was a comic strip grafted onto a transitional period when hip-hop became pop culture and Black art was more dominant than ever. By 1999, McGruder, still living at his parent’s house, had secured a six-figure contract with Universal Press and gotten the strip syndicated by 195 newspapers across the country.

Around the same time he became famous for the strip, McGruder worked to bring it to TV. While the comic had plenty of memorable moments, there’s only so much story to be told within the confines of just a few panels. The Boondocks was made for longer adventures, and, after struggling to find a platform that would allow him to tell the story the way he wanted, he was finally able to prove that when he struck up a deal with Sony Pictures Television to produce an animated series. From there, he partnered with Adult Swim, which gave him creative free rein.

“I’m glad we got on after Dave Chappelle[’s Chappelle’s Show],” McGruder said in 2005. “Chappelle was one of those shows that kind of set the bar. Like, oh right. This is really what you can do with creative freedom. You can really go there.”

The Boondocks animated series, which debuted in November 2005, is a nihilistic cocktail of over-the-top violence, comedic social commentary, and gratuitous N-word usage. The cartoon combines Chappelle-esque surrealism and warped social experiments for sharp satire that expands the bounds of the original comic strip (which McGruder stepped away from in 2006). Here, Huey’s a full-blown domestic terrorist, and Riley dabbles in potentially lethal mischief — both are voiced brilliantly by Regina King, while the late John Witherspoon gave Granddad the classic patriarch touch.

At its best, the series blends heart, message, and hilarity with some surprisingly nuanced characterization and sharp observations about Blackness and its place in the American continuum. As progressive as The Boondocks was considered at the time, though, it wasn’t immune to sexism, homophobia, and an undeniable elitism. Still, when the show was good, it was great, and there was no shortage of genius moments that made the show an Adult Swim standout.

In 2019, Sony Pictures Animation announced that a reimagined version of the series was in development; it’s expected to make its return this year on HBO Max. Today, the original Boondocks cartoon strip turns 25. With a new iteration of the show presumably still on the way, we had no choice but to rank every single episode in the original animated series.

55. “Freedomland” (2014)

Aired: Season 4, Episode 7

Guest Voices: N/A

Original Music: N/A

Classic Quote: “Come on, Huey, not just Black people. I’m progressive enough to force all races to reenact your painful history.” — Ed Wuncler II

For all of the shock of a slavery-themed amusement park — complete with lynching re-enactments and cotton picking — this episode is neither whip-smart nor whimsical. It’s not the only time The Boondocks whiffs on the subject.

54. “Stinkmeaner: Begun the Clone War Has” (2014)

Aired: Season 4, Episode 9

Guest Voice: Edward Asner

Original Music: N/A

Classic Quote: “Fine, I’ll find someone else to make me a master swordsman!” — Granddad

The beginning of this episode finds a clone of Granddad’s nemesis, Stinkmeaner, telling viewers “We’re gonna do some shit we already did and just pretend you didn’t see that shit the first time. That’s right nigga, we don’t respect your intelligence.” What follows is a remix of a season one scuffle between Stinkmeaner and Granddad, this time blown up to pay-per-view proportions. While McGruder wrote and produced the first three seasons, he didn’t participate in the fourth — and this recycled plot helped fuel criticisms that the show had outlasted its own imagination.

53. “The New Black” (2014)

Aired: Season 4, Episode 10

Guest Voice: Tommy “Tiny” Lister

Original Music:Stomp Em in the Nuts

Classic Quote: “We’re doomed. We’ll be blacklisted in Hollywood. Now I’ll never host the Oscars.” — Granddad

After Riley makes the national news for directing a homophobic comment toward a fellow student, he’s extorted by activists fighting for various causes. But this episode’s misguided advocacy is disappointing. Even Huey, usually a voice of reason, downplays Riley’s initial offense. It all feels like a bad-faith dismissal of social issues beyond racism.

52. “Good Times” (2014)

Aired: Season 4, Episode 2

Guest Voices: Eddie Griffin and Phil Morris

Original Music: N/A

Classic Quote: “Oh, we’re too good to be slaves? Our ancestors were slaves.” — Granddad

There’s really only one rule of engagement when it comes to depicting slavery in Black comedy culture: It’s gotta be funny. This Good Times-channelling episode, which finds Granddad agreeing to indentured servitude to repay a debt, misses the mark.

51. “Mr. Medicinal” (2010)

Aired: Season 3, Episode 12

Guest Voice: Mark Hamill

Original Music: N/A

Classic Quote: “I don’t even like the regular me, no one does.” — Granddad

A health scare inadvertently converts Granddad into a fun-loving pothead. But unlike marijuana, this episode won’t have you laughing your ass off.

50. “Early Bird Special” (2014)

Aired: Season 4, Episode 4

Guest Voices: Cree Summer and Jenifer Lewis

Original Music: N/A

Classic Quote: “Trick-ass new grandma told me to. She said reading is how she got rich enough to buy Granddad.” — Riley

Saddled with debt, Granddad becomes a male escort to raise money — a fertile concept that unfortunately feels like a rehash of funnier-the-first-time gags about his love life from previous episodes.

49. “Granddad Dates a Kardashian” (2014)

Aired: Season 4, Episode 6

Guest Voices: N/A

Original Music: N/A

Classic Quote: “People don’t want to watch an old broke dude on TV.” — Granddad

One scene in this Keeping Up With the Kardashians spoof depicts “Kardashia Kardashian” getting black-market butt implants before her ass literally explodes. Seriously.

48. “The Fried Chicken Flu” (2010)

Aired: Season 3, Episode 13

Guest Voice: DeRay Davis

Original Music: N/A

Classic Quote: “Shockingly, people are still eating chicken — willing to risk life and limb for a leg and a thigh.” — News reporter

A mysterious virus takes hold of America just as a new fried chicken combo is announced at a popular fast food joint — an eerie prediction of Covid-era anti-maskers that doesn’t make much of a statement.

47. “Home Alone” (2007)

Aired: Season 2, Episode 10

Guest Voices: N/A

Original Music: N/A

Classic Quote: “Hey, Robert, I’d offer to get your bag, but you a coon.” — Uncle Ruckus

After Granddad takes a Costa Rica vacay to get some peace and damn quiet for once, Huey goes full correctional officer while babysitting a raucous Riley. It’s aimless and light on imagination — an album filler track in an otherwise solid season.

46. “Breaking Granddad” (2014)

Aired: Season 4, Episode 3

Guest Voices: Dawnn Lewis and Jenifer Lewis

Original Music: N/A

Classic Quote: “Truth is, your Granddaddy has always had a hard time with women. I’m not very fit, not very funny, not particularly good at conversations, lord knows I’m not good in bed, but I had money. And as long as I had money, I could have a moderately satisfying sex life.” — Granddad

This nod to Breaking Bad finds Huey making bombs with a mysterious gunk that Granddad bottles and repurposes as a hair relaxer. There’s some social commentary about Eurocentricity and straight hair, you’ve gotta sift through the clumsiness to appreciate it.

45. “I Dream of Siri” (2014)

Aired: Season 4, Episode 8

Guest Voices: N/A

Original Music: N/A

Classic Quote: “Nigga, it’s free money. How can you hate on free money?” — Riley

Granddad lives out the plot of Her, the 2013 film in which Joaquin Phoenix falls in love with an artificially intelligent device. In this entertaining spoof, however, the A.I. in Granddad’s new iPhone wreaks havoc on his life after he rebuffs its advances.

44. “Pretty Boy Flizzy” (2010)

Aired: Season 4, Episode 1

Guest Voice: Michael B. Jordan

Original Music:I Wanna Do Your Wife” and “Getting Drunk Fuckin’ Strippers

Classic Quote: “I let my fans down. Without you, I wouldn’t even have an R&B girlfriend to beat.” — Pretty Boy Flizzy

Tom Dubois gets a lesson in masculinity from Pretty Boy Flizzy, Boondocks’ Chris Brown stand-in who stages crimes to maintain pop culture relevance. While there are some undeniably funny moments — the news clips of unconvincing public apologies for his wrongdoings are quippy critiques of a culture that forgives too often — the general premise underwhelms.

43. “It’s Goin’ Down” (2010)

Aired: Season 3, Episode 15

Guest Voices: Charlie Murphy, Edward Asner, Kym Whitley, and Samuel L. Jackson

Original Music:Stomp Em in the Nuts

Classic Quote: “Allah, make my testicles strong against the boot of the infidel.” — Terrorist

This 24 spoof finds Huey and Special Agent Jack Flowers trying to prevent the bombing of a local building. The over-the-top action scenes — Flowers conducts interrogations by kicking his detainees with a metal boot — and Flowers’ flashbacks about his loved ones dying in extravagantly violent ways make this one solid.

42. “Ballin’’’ (2007)

Aired: Season 2, Episode 8

Guest Voices: N/A

Original Music: N/A

Classic Quote: “This kid sure can dribble, but he shoots like shit” — Commentator

Riley has all the sauce but nothing to put it on in this straightforward episode about the pitfalls of streetball culture. The Shaq impersonation that appears in the opening segment is hilariously spot-on.

41. “Attack of the Killer Kung-Fu Wolf Bitch” (2007)

Aired: Season 2, Episode 6

Guest Voice: Aisha Tyler, DeRay Davis, Kym Whitley, and Tichina Arnold

Original Music: N/A

Classic Quote: “Bitch, this chicken is cold.” — Two of Luna’s ex-boyfriends

After dipping into the world of online dating, Granddad meets a twentysomething stunner named Luna, who turns out to be a murderous kung-fu master that doesn’t take rejection too well. Her showdown with Huey is a highlight.

40. “Invasion of the Katrinians” (2007)

Aired: Season 2, Episode 9

Guest Voices: Cedric The Entertainer, DeRay Davis, Jamai Fisher, and Lil Wayne

Original Music: N/A

Classic Quote: “Tell them we’re not here!” — Granddad

The Freemans house their hilariously ungrateful Hurricane Katrina-surviving relatives, who generate LOL moments by spending their time making Granddad regret that decision. Led by the folksy but manipulative Jericho Freeman (voiced by Cedric The Entertainer), the evacuees complain that the house is messy, while their kids jump on furniture before Granddad taps into Sage Mode pettiness, cutting off the power and relegating his extended fam to cheap lunch meat. It’s funny stuff, but the depiction of Katrina evacuees feels tasteless, especially considering that this episode aired just two years after the natural disaster. (Even worse, Curb Your Enthusiasm beat them to a similar concept by three months!)

39. “The Real” (2006)

Aired: Season 1, Episode 8

Guest Voice: Xzibit

Original Music: N/A

Classic Quote: “As you can see, Dorothy is past her prime. I mean, look at the paint job. This car looks like it needs some lotion.” — Xzibit

Granddad pretends to be blind and sheltering the homeless to land placement on Pimp My Ride and Extreme Makeover Home Edition, respectively. It’s a solid plot and execution — plus, seeing Granddad get called “Bitches” as a nickname never gets old.

38. “Pause” (2010)

Aired: Season 3, Episode 8

Guest Voices: Affion Crockett and Kadeem Hardison

Original Music: N/A

Classic Quote: “I know you think I’m just a light-skinded gardener so poor that I can’t even afford a shirt, but I love me some Jesus — and I love me some you.” — Unnamed actor

What, you thought The Boondocks wouldn’t take on Madea? A filmmaker named Winston Jerome creates a cross-dressing matriarch, citing Jesus as his inspiration. Granddad jumps at the chance to be a leading man in his film, but it turns out Jerome’s cast is actually a cult. The parodying of Tyler Perry’s heavy-handed dialogue and premises are on point, but the episode is tainted by a tinge of homophobia.

37. “Wingmen” (2006)

Aired: Season 1, Episode 13

Guest Voices: Affion Crockett, DJ Pooh, Kym Whitley, Mike Epps, and Niecy Nash

Original Music: N/A

Classic Quote: “I got something to give you, and it’s very near and dear to me, player, pimp… these nuts, nigga!” — Mo

After being asked to deliver a eulogy for an estranged friend, Granddad proves he’s barely able to do that before his old pal trolls him from beyond the grave. Between the quips, Huey also learns how the passage of time can fray friendships.

36. “Smokin With Cigarettes” (2010)

Aired: Season 3, Episode 6

Guest Voices: N/A

Original Music: N/A

Classic Quote: “I do bad things. I hurt people. And I smoke with cigawettes.” — Lamilton Taeshawn

When 7-year-old Florida boy Latarian Milton went viral for stealing his grandmother’s car with no remorse and no chill, you just knew the bizarre story was perfect fodder for The Boondocks. Here, he’s re-created as Lamilton Taeshawn, an imposing child who coerces Riley to raise hell around the city — with nods to films like The Ring, Halloween, and Juice as they do.

35. “Freedom Ride or Die” (2014)

Aired: Season 4, Episode 5

Guest Voices: Dawnn Lewis, Dennis Haysbert, and Phil Morris

Original Music: N/A

Classic Quote: “Oh what a stunning victory, brothers and sisters. You not-fought bravely.” — Sturdy Harris

A young Robert Freeman inadvertently joins the Freedom Riders on their way to 1960s Birmingham, Ala., where a one-sided battle ensues between the Riders, led by the superhuman Sturdy Harris (voiced by Dennis Haysbert, b.k.a. the Allstate guy), and local White supremacists. While satirizing the Civil Rights era is tricky grounds, this episode works because it interacts with the most fundamental issue of non-violent protest: You could very well get your ass beat, and many Freedom Riders did. But that didn’t stop Granddad from wielding his belt as a weapon of mass destruction.

34. “The S-Word” (2007)

Aired: Season 2, Episode 11

Guest Voice: CeeLo Green

Original Music: N/A

Classic Quote: “Extort? Is that what you call the freedom struggle, brother? I supposed you think affirmative action is extortion, too, huh?” — Rollo Goodlove

After a White teacher calls Riley the N-word, he and his shameless patriarch believe they’ve secured the lawsuit bag. They team up with janky activist Rollo Goodlove (CeeLo Green), a play on the likes of Jesse Jackson and Al Sharpton. Things crescendo when Goodlove debates conservative pundit Ann Coulter on TV, only to later reveal they were in cahoots to profit off America’s racism-industrial complex.

33. “Lovely Ebony Brown” (2010)

Aired: Season 3, Episode 11

Guest Voices: N/A

Original Music: N/A

Classic Quote: “I love it that you fight people with a belt. I love it that you’re friends with a pimp named A Pimp Named Slickback. I love it that Riley thinks everything is gay.” — Ebony Brown

Granddad becomes insecure about his age after bagging a younger woman named Ebony Brown. There’s a thinly veiled message about self-love in here lurking behind the meta-humor of Ebony recognizing and appreciating the ridiculousness of Granddad’s life, from his eccentric friends to his insistence on corporal punishment.

32. “The Block Is Hot” (2006)

Aired: Season 1, Episode 14

Guest Voice: Edward Asner

Original Music: N/A

Classic Quote: “No actually, this neighborhood is handling the shooting of an unarmed Black man pretty well.” — Tom Dubois

Tom’s daughter, Jazmine, learns a hard lesson about capitalism after Mr. Wuncler scams her out of her lemonade stand. What begins as an innocent child’s enterprise turns into a collection of human rights violations. Elsewhere, Uncle Ruckus becomes a victim of police brutality. Yet rather than sue the city, he asks for the chance to become a cop — and he gets his wish.

31. “The Uncle Ruckus Reality Show” (2008)

Aired: Season 2, Episode 15

Guest Voices: Affion Crockett, Debra Wilson, DeRay Davis, Donald Faison, and Kym Whitley

Original Music: N/A

Classic Quote: “I got a fraternity for you; it’s called prison. Jail-Phi-Jail.” — Uncle Ruckus

BET concocts its most diabolical scheme yet: giving Uncle Ruckus his own reality show. Shit hits the fan after a genetic scientist tells him he’s 102% African (with a 2% margin of error) and in a morbid moment of self-hatred, he attempts to hang himself while the cameras are rolling. Ruckus’ genuine grief is hilarious; the relief he feels after a BET exec instructs the genealogist to alter the DNA test results to indicate that he’s half-White is just as funny.

30. “Let’s Nab Oprah” (2005)

Aired: Season 1, Episode 11

Guest Voices: Charlie Murphy and Samuel L. Jackson

Original Music: N/A

Classic Quote: “Man, you come straight out of a comic strip.” — Bushido Brown

Growing increasingly aware that Woodcrest authorities will let them get away with anything, Ed Wuncler III and Gin Rummy try to level up their criminal clout by kidnapping Oprah. Predictably, that doesn’t go well, but the episode succeeds due to its randomness (and an epic fight sequence).

29. “The Story of Lando Freeman” (2010)

Aired: Season 3, Episode 10

Guest Voices: Billy Dee Williams, Gerald ‘Slink’ Johnson, and Samuel L. Jackson

Original Music: N/A

Classic Quote: “You are the sack from which I come!” — Lando Freeman

After taking a paternity test, Granddad is forced to bond with a man who calls himself his son, and the results are as funny as they are heartwarming. Lando Freeman tries to relive a whole childhood in just a few days — at least until Granddad discovers the test results were falsified.

28. “Riley Wuz Here” (2006)

Aired: Season 1, Episode 12

Guest Voices: N/A

Original Music: N/A

Classic Quote: “OK… Niggerize Me.” — Huey

Riley dives into the world of graffiti, learning about how to make your mark on the world through art. After tagging up various locations around the neighborhood, he creates a mural that brings Granddad to tears in one of the show’s most affecting moments (soundtracked by Tom Scott and The California Dreamers’s “Today” and Pete Rock and CL Smooth’s “They Reminisce Over You (T.R.O.Y.)”).

27. “The Hunger Strike” (2008)

Aired: Season 2, Episode 14

Guest Voices: CeeLo Green, Debra Wilson, Donald Faison, and Tavis Smiley

Original Music: N/A

Classic Quote: “Now, is Tigga short for Tiger and nigga, or are you just a big ol’ fan of Winnie The Pooh?” — Rollo Goodlove

The Boondocks had no shortage of elitist takes, but this takedown of BET — depicting the network as an evil empire dead-set on the destruction of Black people — is as funny as an episode of ComicView. Cartoon Network originally shelved this episode, which depicts BET execs Debra Lee and Reginald Hudlin as Debra Leevil and Wedgie Rudlin, respectively.

26. “The Red Ball” (2010)

Aired: Season 3, Episode 3

Guest Voices: Charlie Murphy, Edward Asner, and Lauren Tom

Original Music: N/A

Classic Quote: “But were Americans. We don’t quit just because we’re wrong. We just keep doing the wrong thing until it turns out right.” — Mr. Wuncler

The nefarious Mr. Wuncler bets the future of Woodcrest on an international kickball game, and it’s up to Huey to save the day in this spot-on parody of a Samurai Champloo episode (“Baseball Blues”). This one flips anime tropes for some funny moments while adding commentary on reckless American business and shady sports dealings. Light on laughs but high on anime-influenced action scenes, this episode is a standout.

25. “It’s a Black President, Huey Freeman” (2010)

Aired: Season 3, Episode 1

Guest Voices: Bill Maher, Kym Whitley, and Werner Herzog

Original Music: Dickriding Obama

Classic Quote: “I don’t know who this Huey Freeman is, but he doesn’t stand for what I stand for, and I denounce and repudiate and condemn him… Basically, fuck him.” — Barack Obama

This clever mockumentary acts as a time capsule of the moment Barack Obama took office, rounding up commentary from the youth who supports him because he’s Black (Riley), the clout-chasing celeb who is clueless on politics (Thugnificent), the civil rights activist who feels Obama is a reward for their hard work (Granddad), and the skeptics who are unclear how Obama will change America (Huey). Some clever jokes about Ruckus’ misery help tie together an inventive season three premiere.

24. “Thank You for Not Snitching” (2007)

Aired: Season 2, Episode 3

Guest Voices: Affion Crockett, Bill Duke, Charlie Murphy, DeRay Davis, Mos Def, and Samuel L. Jackson

Original Music: N/A

Classic Quote: “I’m watching, alright — I’m watching this whole neighborhood become a bunch of tattletales.” — Granddad

Granddad doesn’t believe in snitching, but changes his mind once his whip gets stolen. Riley knows Gin Rummy and Ed Wuncler III were behind the carjacking, but clings steadfast to the code of the streets, defying the police, an over-the-top neighborhood watch group, and his own grandfather. It’s a classic case of The Boondocks hilariously bending a hip-hop concept as far as possible before it snaps.

23. “The Story of Gangstalicious Part 2” (2008)

Aired: Season 2, Episode 13

Guest Voices: Busta Rhymes, Chris Williams, DeRay Davis, Fatman Scoop, Katt Williams, Mos Def, and Snoop Dogg

Original Music: Homies Over Hoes

Classic Quote: “I don’t think ‘Homies over Hos’ is a sentiment that A Pimp Named Slickback can cosign, Riley. Don’t get me wrong, A Pimp Named Slickback will put a lot of things over a ho. Money over a ho, always. Brand new gators over a ho, absolutely. A turkey sandwich with just tomato, guaranteed. But homies? Oh no.” — A Pimp Named Slickback

Riley has an identity crisis upon learning that his favorite rapper, Gangstalicious, may be a homosexual man. The episode challenges homophobia, but not without falling into its traps.

22. “The Fund-Raiser” (2010)

Aired: Season 3, Episode 7

Guest Voice: Charlie Murphy

Original Music: N/A

Classic Quote: “The first rule of fundraising is: Don’t give nothin’ to nobody, period. No charities, homeless people, Salvation Army, Red Cross, starvin’ Africans — nothin’! You can’t be raising funds and giving funds away at the same time.” — Riley

Riley Escobar lives up to his moniker when he finds a loophole in the candy fundraising game and goes full Tony Montana. Shady school principals willing to look the other way, unexpected Girl Scout cookie turf wars, and a massive shootout blend brilliantly. The image of Riley decked out in an icy-white mink is one of the series’ most enduring screengrabs.

21. “A Huey Freeman Christmas” (2005)

Aired: Season 1, Episode 7

Guest Voice: Quincy Jones

Original Music: N/A

Classic Quote: “I heard they hired extra security to protect you. That’s a bitch move, Santa. I’m coming for that ass again. Until you pay what you owe.” — Riley

Huey turns his school theater department upside down when he fires his schoolmates and inexplicably enlists Quincy Jones, Denzel Washington, and Angela Bassett for his ambitious, samurai-incorporating Christmas play, The Adventures of Black Jesus. Meanwhile, Riley seeks revenge on Santa Claus due to unanswered wishes from years past. (“Dear Santa,” he writes in a letter to the North Pole, “you are a bitch-ass nigga.”) Packing a BB gun, he spends the whole episode plotting to light up St. Nick like a Christmas tree.

20. “Bitches to Rags” (2010)

Aired: Season 3, Episode 2

Guest Voices: Charlie Murphy, Denzel Whitaker, DeRay Davis, and DJ Vlad

Original Music: Booty Butt Cheeks,” “I Got Way Too Many Cars in My Driveway,” and “Terrible in Terrabelle

Classic Quote: “‘Hey Thugnificent, is it ‘Booty Butt Cheeks’ or ‘Move Them Butt Cheeks’?’ Nigga, who gives a fuck? It’s a song about butt cheeks!” — Thugnificent

Years before rappers were being shamed for working for Lyft, The Boondocks dropped this tragically accurate period piece about rappers adjusting to life after stardom. The subject is Thugnificent, a gangsta rapper who is losing attention to younger rappers making more dance-friendly bops. His attempts to reclaim his stardom play out like a compilation of failed rapper comeback tactics from the 2010s: He drops an Auto-Tune album, is interviewed by DJ Vlad, and starts a beef with a teenage rapper — only to be clowned for being old, washed, and desperate. The game is the game.

19. “A Date With the Health Inspector” (2005)

Aired: Season 1, Episode 5

Guest Voices: Charlie Murphy, Samuel L. Jackson, and Terry Crews

Original Music: N/A

Classic Quote: “File sharing is illegal, and I’m not gonna be anally raped so you can listen to Usher.” — Tom Dubois

At the beginning of this Tom Dubois origin story, we learn that it’s a fear of being sodomized in jail that led him to being the law-abiding square he is today. After he’s arrested for a murder he didn’t commit, he enlists Huey to prove his innocence. There are some laughs, but the central joke — prison rape — is a bad look.

18. “The Story of Catcher Freeman” (2008)

Aired: Season 2, Episode 12

Guest Voices: DeRay Davis and Donald Faison

Original Music: Take Our Black Asses Outta Here

Classic Quote: “Hey, master? Won’t you do me a favor and master these nuts in your mouth, nigga!” — Unnamed slave

Before Django Unchained, there was the legend of a man named Catcher Freeman, who, depending on the storyteller, was either a Malcolm X–Zorro hybrid, a slave catcher, or an opportunistic house negro. With on-point action flick parodies and some funny commentary, the three Rashomon-style recountings, delivered by Granddad, Uncle Ruckus, and Huey, respectively, are rendered in some laugh-out-loud details.

17. “A Date With the Booty Warrior” (2010)

Aired: Season 3, Episode 9

Guest Voices: Clifton Powell, Lawrence Gilliard Jr., Kevontay Jackson, and John Landis

Original Music: N/A

Classic Quote: “My booty is mine/it belongs to me/you cannot take/my boo-ty” — Tom Dubois

Tom confronts his greatest fear in the worst possible setting: a prison. There, he finds himself the prey of a convicted rapist known as the Booty Warrior in an episode that satirizes Scared Straight. Eleven years after the episode first aired, the premise is cringier than ever, yet Tom’s mortal fear of sodomy remains hilarious.

16. “…Or Die Trying”

Aired: Season 2, Episode 1

Guest Voices: Affion Crocket, Mo’nique, and Snoop Dogg

Original Music: N/A

Classic Quote: “See! Shows what you know. I’ve seen funny lynchings.” — Granddad

Everyone knows movie theaters are too damn expensive, but this episode is worth the cost of admission. Granddad refuses to break the bank to go see a fictional Soul Plane sequel, so he cuts corners at all costs — sneaking himself, his grandchildren, and Jazmine in without paying for admission, not to mention stashing neckbones and meatloaf to eat while the film plays. It’s exaggerated, yet relatable. That is, until Uncle Ruckus, who is working as an usher, catches on, eventually engaging in a nunchuck battle with Huey.

15. “Stinkmeaner Strikes Back” (2007)

Aired: Season 2, Episode 4

Guest Voices: Ghostface Killah and Terry Crews

Original Music: N/A

Classic Quote: “There is powerful niggatry at work.” — Uncle Ruckus

Stinkmeaner returns from the dead by possessing Tom Dubois’ body. Only a riddle from the ghost of Ghostface Killah (who’s still alive) and a mutual hatred of Black people can set things right. Uncle Ruckus’ exorcism — one that uses nooses, whips, a job application, and the chant “Nigga, get yo Black ass outta here” — is the best part of a sequel episode that lives up to its predecessor.

14. “Shinin’” (2007)

Aired: Season 2, Episode 7

Guest Voices: Busta Rhymes, Charlie Murphy, DeRay Davis, and Snoop Dogg

Original Music: N/A

Classic Quote: “Riley, that’s the whole part of a crew, nigga. So you ain’t never got to worry about handling shit like a man.” — Flonominal

After Thugnificent inducts him into his Lethal Interjection Crew, Riley learns the downside of being lit when he gets strongarmed for his LIC chain by a powerful middle schooler named Butch Magnus. Attempts to retrieve the necklace only lead to subsequent beatdowns, including one where Butch drops Flow, Riley’s grown-ass rapper homie, before claiming the chain was fake and returning it.

13. “The Color Ruckus” (2010)

Aired: Season 3, Episode 14

Guest Voices: Don ‘D.C.’ Curry, Luenell, and Star Jones

Original Music: N/A

Classic Quote: “Baby, why don’t we read about Eli Whitney instead? He invented the cotton gin. He was a great White man, just like you.” — Bunny Ruckus

This Uncle Ruckus origin story manages to be as funny as it is tragic. We learn that Ruckus’ self-hate originates from his mother, who would rather credit George Washington Carver with the rise in peanut allergy deaths than give him props for revolutionizing the peanut. We also learn that his physically deformed face comes from injuries inflicted on him by his abusive father, Mister, a parody of Danny Glover’s The Color Purple character of the same name. When his grandmother travels to see him in her literal dying days, Ruckus comes face-to-face with his family again and stands up to his father one last time. By the end of the episode, Ruckus finds a level of catharsis no one expected, once again showcasing McGruder’s talent for finding poignancy in the absurd.

12. “The Garden Party” (2005)

Aired: Season 1, Episode 1

Guest Voices: Billy West, Charlie Murphy, Dawnn Lewis, and Edward Asner

Original Music:Don’t Trust Them New Niggas

Classic Quote: “In 30 years, that boy will be the president of the United States, and he’ll still be a fucking idiot.” — Mr. Wuncler

The series’ opening episode, in which the Freemans acclimate to their new suburban neighborhood, sets the tone for the whole show. Huey fires off anti-government conspiracy theories at a crowd of unsuspecting White people, all of whom are too impressed with his vocabulary to do anything but applaud. Later, Riley blasts rich, unstable Iraq war veteran Ed Wuncler III through a window with a shotgun. Violence, racial commentary, a dig at then-U.S. president George W. Bush — the formula works because it works.

11. “Stinkmeaner 3: The Hateocracy” (2010)

Aired: Season 3, Episode 5

Guest Voices: Aries Spears, Charlie Murphy, and Michael Jai White

Original Music: N/A

Classic Quote: “Fascinating creature, the crab. Got that hard exterior. But he ain’t all that dangerous, except to another crab. Dumb as all hell. Can’t even walk straight. Matter of fact, the only thing a crab is good for is holdin’ back other crabs. A crab don’t wanna see another crab make it. Crab is like, ‘If I’m gonna die, we all gonna die.’ I admire that. We all gotta die sometime, might as well help each other get there.” — Rufus Crabmiser

General Stinkmeaner’s family (a.k.a. The Hateocracy) hunts down the Freemans, looking to avenge his death. The result is a fighting sequence so violent that it was the first Boondocks episode to earn a TV-MA-V rating. The episode blends kung fu and Black culture as only The Boondocks can. Bushido Brown, a play on 1970s film stars like Jim Kelly, mimics a Bruce Lee move from Enter the Dragon, and Huey fights a dude who looks like an older version of JJ from Good Times. Ultimately, the Hateocracy is brought down by a force that not even their time-tested hatred and superhuman martial arts techniques can circumvent: the police.

10. “The Itis” (2005)

Aired: Season 1, Episode 10

Guest Voices: Edward Asner and Kym Whitley

Original Music: N/A

Classic Quote: “Bitches love free food, Robert.” — Mr. Wuncler

What’s good for the soul ain’t always good for the heart. When it comes to Granddad and his fatty soul food, it’s damn near lethal. Here, Granddad teams up with Mr. Wuncler to open a restaurant that serves gluttonous dishes like sausage and waffle fried chicken lasagna (!) or mayonnaise-drizzled chitlins. The restaurant’s a hit (there are even beds for post-meal naps), but its existence gradually destroys the neighborhood, turning suburbanites into zombified fried chicken fiends. It’s an imaginative look at the intersection of culture and cuisine, and a deft metaphor for the dangers of unhealthy eating.

9. “Guess Hoe’s Coming to Dinner”

Aired: Season 1, Episode 3

Guest Voice: Katt Williams

Original Music: N/A

Classic Quote: “No, it’s a Pimp Named Slickback, like A Tribe Called Quest. You say the whole thing.” — A Pimp Named Slickback

Granddad unwittingly begins dating a twentysomething sex worker — a “fake-ass Mariah Carey,” according to Riley — who’s all too happy to spend his money. The respectability politics and misogyny are laid on thick, but the hilarious series introduction of the Katt Williams-voiced character A Pimp Named Slickback is unforgettable.

8. “The Story of Gangstalicious” (2005)

Aired: Season 1, Episode 6

Guest Voices: DJ Pooh, Kym Whitley, Mos Def, and Sway Calloway

Original Music:Play It for the Jury

Classic Quote: “Gangstalicious Resurrection? The nigga ain’t dead!” — Huey

The Boondocks takes on gangsta rap, twisting every trope to its absurd limits. The title character, voiced by Mos Def, has become hip-hop’s hottest artist after surviving a savage shootout. His thugged-out image is such a shtick, after he’s been struck by bullets mid-concert, fans think it’s part of the performance.

7. “Tom, Sarah and Usher” (2007)

Aired: Season 2, Episode 2

Guest Voices: Affion Crockett and Katt Williams

Original Music: N/A

Classic Quote: “Me not calling her a bitch would be disrespectful to you.” — A Pimp Named Slickback

Date night turns into a playground for Tom’s insecurities when Usher pulls up and sweeps his wife, Sarah, off her feet. The only logical thing to do next: consult A Pimp Named Slickback on how to get out of the doghouse and get his lover back. Come to see Tom sing “Burn”; stay to watch him get his ass beat by an R&B superstar.

6. “The Story of Jimmy Rebel” (2010)

Aired: Season 3, Episode 4

Guest Voices: N/A

Original Music: N/A

Classic Quote: “Well, we are called Racist Records. I think people expect a certain amount of racism from us.” — Racist Records employee

Racist country music star Jimmy Rebel learns a hard truth about prejudice after engaging in an epic bromance with Uncle Ruckus, who shares his talent for meshing inventive racial insults with backroads country tunes. This one succeeds because McGruder brings sincerity to the characters’ interactions, simultaneously highlighting the stupidity of racism while creating a wholesome character arc for someone you should hate. Whether they’re laughing at a slave getting whipped in Amistad or playing Twister, Ruckus and Rebel engage each other with convincing warmth and sincerity that almost makes you forget they’re two bigots. After Jimmy unsuccessfully tries to get White audience members to embrace Uncle Ruckus, he realizes that racism has nothing to do with attitude or integrity. His fans simply don’t like Black people because they’re Black.

While Adult Swim has removed the episode from its website and HBO Max has made it unavailable to stream due to its controversial nature, “The Story of Jimmy Rebel” is as effective as any episode in the Boondocks catalog.

5. “The Story of Thugnificent” (2007)

Aired: Season 2, Episode 5

Guest Voices: Busta Rhymes, DeRay Davis, Nate Dogg, Snoop Dogg, Sway Calloway, and Xzibit

Original Music:Booty Butt Cheeks,” “Eff Granddad,” “Untitled Thugnificent Diss From Granddad

Classic Quote: “Did you just congratulate me for reading?” — Huey

Coming straight outta Terrible Terrabelle, Ga., rapper Thugnificent moves to Woodcrest — much to the chagrin of his new neighbor, Granddad. The two get into a beef that leads to a classic Boondocks rap song featuring a fire Nate Dogg hook, scathing verses from Snoop Dogg and Busta Rhymes, and a “Dre Day”-esque video complete with a Granddad imposter.

4. “The Passion of Ruckus” (2006)

Aired: Season 1, Episode 15

Guest Voices: N/A

Original Music: N/A

Classic Quote: “Black people are cursed…That’s why we in the ghetto, that’s why we in jail, that’s why we on UPN… He turned water to wine, he could’ve turned UPN to CBS!” — Uncle Ruckus

“The Passion of Reverend Ruckus” blends all of The Boondocks’ best traits for an episode that’s as funny as it is inventive and touching. After meeting Ronald Reagan in White Heaven, Uncle Ruckus discovers that he’s got terminal cancer, so he founds a church on anti-Blackness, and Black people present themselves so they can save their mortal souls by being smacked by Ruckus at the altar. Meanwhile, Huey’s on a mission to save an ex-Black Panther who’s facing execution after being wrongly convicted of murder.

Ruckus’ church of redemptive racism is the peak of Boondocks’ creativity: appalling, hilarious, and too strange to be replicated. That’s all enough for it to be a great episode. But the way the conclusion ties into Huey’s faith, the possibility of a higher power, and our inability to understand it — while offering a neat resolution to Ruckus’ cancer, Huey’s incarcerated friend, and Huey’s belief in anything — makes this one of The Boondocks’ very best episodes.

3. “Granddad’s Fight” (2005)

Aired: Season 1, Episode 4

Guest Voice: Terry Crews

Original Music: N/A

Classic Quote: “Granddad, Rodney King just called and said, ‘Damn, I thought I got my ass whooped.’” — Riley

In a case of putting pride above all else (etched into the culture as a “nigga moment”), Granddad gets into a street fight with a person he should’ve been able to ignore — in front of people who shouldn’t have let it happen. The result, a humiliating loss to a blind man named Colonel H. Stinkmeaner, exemplifies The Boondocks’ offbeat, satirical genius. Believing his opponent to have heightened senses, Granddad mercilessly beats him to death in their rematch, a classic example of when keepin’ it real goes wrong.

2. “Return of the King” (2006)

Aired: Season 1, Episode 9

Guest Voices: DJ Pooh and Kym Whitley

Original Music: N/A

Classic Quote: “Will you ignorant niggas please shut the hell up!” — Martin Luther King Jr.

In one of The Boondocks’ most controversial episodes (and that’s saying a lot!), Martin Luther King Jr. is dropped in modern times only to find that the world has moved on without him. And quite frankly, he’s shocked by what he encounters: The Man bastardizing his image and message; hip-hop culture exhibiting stereotypical behavior; the damn McRib. While his speech wades deep into respectability politics — including calling a Black crowd some “shiftless niggas” — this fan fiction (which won a Peabody Award) is one of the series’ most creative premises.

1. “The Trial of Robert Kelly” (2005)

Aired: Season 1, Episode 2

Guest Voice: Adam West

Original Music: N/A

Classic Quote: “Every famous nigga that gets arrested is not Nelson Mandela.” — Huey

Fifteen years ago, R. Kelly was still a superstar who could serve up Billboard Hot 100 singles thanks to fans who were willing to ignore one thing: He’d been credibly accused of sexually assaulting teenage girls. Here, The Boondocks unpacks that cognitive dissonance, making a trenchant statement on the consequences of celebrity worship. The plot peaks during a criminal trial in which a lawyer panders to the court with wild red herrings that paint Kelly as a freedom-fighter standing against racism. Kelly breaks out into song, and despite Huey’s calling out the charade, he wins over the jury and spectators. Until late 2018, that’s pretty much how it went in real life, too.