The first part of our Top 20 list highlighted a lot of minor celebrities that had no business being in a boxing ring. Paula Jones, William Perry, and Grant Bovey all appeared to spend little time training for their fights, making them among the five worst celebrity boxers of all-time. The rest of the list features more prepared fighters for one reason or another, but their performances still weren’t great.

 

  1. Jose Canseco

    Jose Canseco helped kickstart celebrity boxing once again in the United States. He has entered the ring several times since his first fight in the summer of 2008, but he hasn’t been too impressive despite his large frame. Canseco was knocked out in the first round by 5’9 Vai Sikahema in the first round despite bragging that he had multiple black belts, and he had to settle for a draw against the diminutive Danny Bonaduce several months later. The slugger finally scored a win with a victory over Todd Poulton, and he also beat Tareq Salahi in 2011. However, he tried to get his brother Ozzie Canseco to fight in his place that same year, and he lost a bout to a Barstool Sports employee in February 2021.

     

  2. Aaron Carter


    Former teen heartthrob Aaron Carter tried to lengthen his 15 minutes of fame in the summer of 2021 by taking on NBA veteran Lamar Odom. Carter was not expected to perform well by the fight odds ahead of the match, and he was knocked out in the second round by Odom.

  3. Hornswoggle

    One of the worst celebrity boxing matches in recent memory featured former WWE and TNA wrestler Hornswoggle. He took on Jeremy Smith in the spring of 2021 at Rough N’ Rowdy 14 on Barstool Sports, and he was defeated by second round TKO.

  4. Coolio

    Rapper Coolio was knocked down multiple times by former Baywatch television star Jeremy Jackson on his way to suffering a TKO loss in the third round. Both Coolio and Jackson kept their shirts on the whole bout, but it was clear that Jackson was in much better shape.

  5. Tonya Harding

    Disgraced figure skater Tonya Harding made easy work of Paula Jones in the very first Celebrity Boxing on FOX. That led to Harding launching a professional boxing career, and she lost her debut on the undercard of a Mike Tyson PPV in February 2003. Harding went on to win three straight bouts by unanimous decision, but she was pummeled in consecutive fights and called it quits afterwards.

  6. Devon Larratt

    World champion arm wrestler Devon Larratt bit off a little more than he could chew when he faced World’s Strongest Man Hafthor Bjornsson in September 2021. Bjornsson won by first-round TKO as the referee stepped in to make sure Larratt didn’t receive any more punishment.

  7. Ben Askren

    Former MMA star Ben Askren was trumpeted by some observers as a real fight for Jake Paul. Askren wasn’t much of an underdog by the boxing betting odds, as he was an MMA champion and one of the best grapplers in the world. He proved he was unable to stand and trade with Paul though, being knocked out within two minutes by the more physically imposing Paul.

  8. Nate Robinson

    Prior to beating Ben Askren, Jake Paul entered the ring with diminutive NBA veteran Nate Robinson as part of the undercard for the Mike Tyson and Roy Jones Jr. exhibition on Triller in November 2020. Robinson was at a significant size disadvantage, and he ended up being on the receiving end of a vicious knockout. Paul sent him to the canvas in the first round before landing a right that led to Robinson being knocked out cold in the second round.

  9. Ricky Gervais

    British comedian Ricky Gervais ended up beating Grant Bovey in The Fight in 2002. Neither celebrity acquitted themselves well though, and it was one of the sloppiest bouts we saw in the first era of celebrity boxing in the early 2000s.

  10. Dave Mirra

    Ellismania has featured a few different celebrity fights over the years, as some of Jason Ellis’ extreme sports friends entered the ring in order to test their mettle. Former BMX star Dave Mirra lost to two-time X-Games gold medalist Brian Deegan in September 2011, and Mirra lost in the eighth round to Deegan. It was a respectable effort by both parties though.