Before Jake and Logan Paul: The curious history of celebrity boxing

Karim Zidan delves into the strange and unusual history of celebrity boxing, including early adopters like Vanilla Ice and Kim Kardashian.

Aaron Carter’s boxing debut did not go as planned.

The American singer, who rose to fame as a pre-teen popstar in the late 1990s, was defeated by former NBA star Lamar Odom at a celebrity boxing match held at the Showboat in Atlantic City, New Jersey on June 11, 2021. Odom was declared the winner after he knocked out Carter in the opening round of their anticipated bout.

Despite the 10-inch difference in height between Odom and Carter, the latter was graceful in defeat. He congratulated Odom on Twitter, praised him for being “so strong,” and revealed that the fight was “so much fun!!!!”

“I actually had a blast so y’all can say what you want. But I don’t see you at 6’ fighting a giant. Takes a bow*,” Carter wrote on Twitter.

The Odom vs Carter celebrity bout took place a week after YouTube sensation Logan Paul faced off against boxing great Floyd Mayweather. Former NFL wide receiver Chad Johnson also took part in an exhibition bout against MMA veteran Brian Maxwell on the Mayweather-Paul undercard.

While Mayweather and Paul went the full eight-round distance with no winner announced, it reportedly sold more than one million pay-per-view buys, emphasizing the growing demand for celebrity boxing bouts between larger-than-life personalities. From growing calls for exhibition bouts that shed quality in exchange for absurdity and celebrity status, to emerging fight organizations dedicated to hosting sensationalist bouts, there is no shortage of interest in the bizarre world of celebrity boxing.

The history of modern celebrity boxing can be traced back to 1994, when American actor and comedian Danny Bonaduce stepped into the ring against former Teen Idol Donny Osmond in a charity exhibition match.

The rivalry began on Chicago radio personality Jonathon Brandmeier’s WLUP-FM afternoon radio program, where Brandmeier goaded the two into a fight after Osmond had teased Bonaduce for his workout routine. Both in their mid-30s, Osmond and Bonaduce entered Chicago’s China Club for a three-round bout with limited training and preparation. The fight produced little excitement and eventually ended with Bonaduce being awarded a split decision victory. The result led to a post-fight confrontation where Bonaduce insulted Osmond’s sister, fellow singer Marie Osmond.

“I kick your (butt) and then am nice to you, and then you complain? What a woman!” Bonaduce reportedly said during the exchange.

In 2002, FOX announced a new television show called Celebrity Boxing, in which celebrities with diminished stardom were pitted against each other in exhibition bouts. Two hour-long specials were aired in total, featuring acclaimed ring announcer Michael Buffer and a national anthem sung by the Backstreet Boys vocalist Howie Dorough. The first episode featured the return of Bonaduce, who defeated fellow actor Barry Williams, who is best known for his role as Greg Brady on The Brady Bunch. The episode also featured a bout between Diff’rent Strokes actor Todd Bridges and rapper Vanilla Ice, who had UFC veteran Tank Abbott in his corner.

The second episode, which aired on May 22, 2002, was headlined by an intergender bout between former WWE superstar Joanie “Chyna” Laurer and rapist Joey Buttafuoco. Chyna lost by majority decision. Other notable fights included Saved by the Bell star Dustin Diamond against 70s sitcom star Ron Palillo. Overall, the show was considered a failure and was ranked as number 6 on TV Guide’s “50 Worst TV Shows of All Time.”

Despite FOX”s failed attempt to bring celebrity boxing to a mainstream audience, it did not discourage others from trying. Comedian Ricky Gervais faced television personality Grant Bovey in a celebrity bout that was watched by five million people in 2002. However, the British Boxing Board of Control denounced the charity event as “dangerous and irresponsible,” pressuring the BBC to scrap its celebrity boxing specials.

“It is with regret that without the backing of the boxing authorities we have asked our celebrities to stop training, and put plans for the remaining bouts on hold,” a BBC spokeswoman said at the time. “Our record for safety and working with the best in business has been paramount throughout production of BBC2’s The Fight. We are extremely proud of the programmes and our celebrity boxers’ contributions to charity.”

While only a handful of celebrity fights would be approved in the UK in the future, the phenomenon continued to spread around the world. In 2007, former UFC tournament winner Oleg Taktarov stepped into the ring against Swedish actor Dolph Lundgren, better known as Ivan Drago from Rocky IV, as a “King of the Ring” event in Russia. Taktarov won by unanimous decision.

In 2009, ABC produced a reality show starring Lakers legend Shaquille O’Neal. The show, entitled Shaq vs., saw O’Neal challenge top athletes in their own sports. During the first season, O’Neal challenged Oscar De La Hoya to a five-round sparring match-up De La Hoya won by unanimous decision. The following year, O’Neal challenged Shane Mosley, who also defeated the basketball legend by unanimous decision.

Celebrity boxing continued to permeate reality television shows at the time. During an episode of Keeping up with the Kardashians in 2009, the Kardashians hosted the Kardashian Charity Knock-Out, where budding boxers faced members of the Kardashian family in a charity exhibition bouts. This included Kim Kardashian herself, who stepped into the ring clad in pink boxing gear but was unable to withstand the beating dealt by her opponent, Tamara.

“It was absolutely insane [but] at the end of the day, we did this for charity and that’s what counts,” Kim reflected in her blog. “You can try to bring the Kardashians down…but we’re a strong family.”

While celebrity boxing mainly served as a sideshow or circus act adjacent to actual sports events, it also managed to raise funds and awareness for a variety of important causes. In October 2012, Actor Ruby Rose defeated boxer Yi Sia in a charity boxing match that raised money for headspace, a youth mental health foundation based in Australia. The BBC returned to celebrity boxing in 2018, hosting a series of Celebrity Boxing for Sport Relief events which raised money to help vulnerable people in both the UK and the world’s poorest countries.

While benefiting charities and important causes is one of the positive aspects of some celebrity boxing events, the latest trend of exhibition bouts have been nothing short of commercial enterprises that result in millions of dollars in profits for the celebrities involved.

On Feb. 3, 2018, British YouTuber KSI defeated fellow YouTuber Joe Weller in a fight that drew 21 million views within 24 hours. KSI, who was awarded the YouTube Boxing Championship Belt, quickly called out the Paul brothers, which led to an agreement that Logan Paul would fight KSI, while their younger brothers Deji Olatunji and Jake Paul would fight each other in the co-main event. The event took place on Aug. 25, 2018; Paul vs KSI was deemed a majority draw while Jake Paul defeated Deji Olatunji by TKO in the fifth round. Although official details were not released, one estimate of the total revenue is believed to be £150 million, including ticket sales, PPV revenue and merchandise sales.

KSI and Paul took part in a rematch the following year, this time in a professional boxing bout which KSI won by split decision. The fight series cemented Paul as a mainstay in the combat sports world, and he has since called out several notable fighters and celebrities for future fights. His brother Jake also made a name for himself with wins against the likes of former NBA player Nate Robinson and, most recently, a win against former Bellator and ONE champion Ben Askren. Jake Paul is now expected to face former UFC champion Tyron Woodley in the squared circle.

While celebrity boxing emerged in the 1990s as a medium for has-been celebrities to settle scores, it has since gone through various iterations: first as a reality show’s circus act, then as a platform for social causes and to raise funds for charity, and, most recently, as a bizarre niche within combat sports, fully equipped with its own fan base and cast of characters such as the Paul brothers.

Part 2 of BloodyElbow’s series on the history of celebrity boxing will look at the politicians who stepped into the squared circle as part of their political campaigns.