6 Most Embarrassing Celebrity Boxing Matches, Ranked
Photo: Joe Scarnici / Getty Images; Design: Qadir El

6 Most Embarrassing Celebrity Boxing Matches, Ranked

Blac Chyna vs. Alysia Magen got nothing on these famous-folk fights

6. Coolio vs. Jeremy Jackson (2011)
Coolio was damn near 50 years old when he declared it was “more than likely” he would beat the star of Baywatch in the squared circle. Yet after two rounds of the 31-year-old Jackson treating the rapper’s head like a game of whack-a-mole, Coolio took a fantastic voyage to the mat—and an eventual loss. That ain’t gangsta.

5. Floyd Mayweather vs. Logan Paul (2021)
Dawg. If we wanted to see two grown-ass men hug it out on television, we’d just watch Uncle Phil consoling Will Smith on The Fresh Prince of Bel-Air.

4. Bigfoot vs. Loch Ness Monster (1998)
Shorter than a Tyson fight in the '90s, this showdown on MTV’s Celebrity Deathmatch saw Sasquash chopped in half by Nessie's tail in just six seconds. Godzilla vs. Kong could never.

3. Jake Paul vs. Tyron Woodley (The Rematch) (2021)
In his professional boxing debut, an MMA fighter was destroyed by a YouTube personality. Hard to believe, eh? Yet that was the fate of Tyron Woodley, who, word to James Todd Smith, took two L’s in less than four months’ time. After losing via split decision to rising boxer/Trump-supporting vlogger Jake Paul, terms for a rematch included Woodley getting inked with I LOVE JAKE PAUL anywhere on his body. The middle finger tat eventually faded, but the memory of Woodley getting knocked the fuck out will live on forever.

2. Sticky Fingaz vs. Simon Woodstock (1998)
In “How to Rob,” 50 Cent gave the perfect post-fight breakdown for this squabble between a skateboarder and dude who raps the last verse of “Slam”: “I’ll beat your ass like that White boy on MTV.”

1. Nate Robinson vs. Jake Paul (2020)
Imagine talking shit for months about how you’re going to demolish your opponent in a fight before doing the exact opposite. OK, now imagine Snoop Dogg commentating said knockout, attempting to bring you back to life with hymnal singing and invoking the holy spirit. And then, imagine footage of your knockout becoming the subject of countless memes poking fun at your unconscious body. Once upon a time, we promised to never speak of this again. We lied.