Kim Kardashian vs. Tamara Frapasella
If you know anything about Kim Kardashian, she's probably not the first person to come to mind when you think of celebrity boxing. But she did it back in 2009. The reality star, business mogul, and mom of four took part in the match on screen for her reality show "Keeping Up with the Kardashians." Her goal was to raise money for a charity, the Dream Foundation, which helps terminally ill adults.
Kardashian watched as other members of her family boxed, including her stepfather, Bruce Jenner, and her brother, Rob Kardashian. While Jenner, an athlete, won the match, Rob wasn't so lucky and ended up in the hospital. Kim was hesitant to step into the ring, but she wanted to be strong for a terminally ill fan. She admitted she'd only begun training the week before the event. Kardashian lost her match to actress and athlete Tamara Frapasella, and she claims it's the most pain she's ever been in in her life.
Idris Elba vs. Lionel Graves
As a child, actor Idris Elba joined a boxing club, and he says it taught him discipline and changed his life. So, that may be why he came up with an idea for a TV show called "Idris Elba's Fight School," a show designed to help troubled youth change their ways through learning to box. But the movie star's association with boxing doesn't end there.
In 2016, Elba decided to train in kickboxing and mixed martial arts and make an attempt at boxing professionally. The Discovery Channel even turned his training into a documentary. The actor went on to participate in a single match with a more experienced boxer Lionel Graves in London and won. However, these days, he's sitting on the sidelines. He claims his mother and his wife both forbade him from returning to the ring.
(Image via Harald Krichel, CC BY-SA 4.0, via Wikimedia Commons; Instagram)
Chad Ochocinco Johnson vs. Brian Maxwell
Former NFL wide receiver Chad Ochocinco, aka Chad Johnson, is one of the best athletes to ever play professional football, so it may not seem so far-fetched for him to try his hand at boxing as well. The former Pro Bowler's life is anything but boring, and he claims that his goal in life is to take chances and mark as much off his bucket list as he can.
In 2021, he did just that. Johnson stepped into the ring with professional boxer and mixed martial artist Brian Maxwell, and he held his own for a while. No winner was declared, but fans came away from the match impressed with the football star's skills, even if he did get knocked down in the fourth round.
Donny Osmond vs. Danny Bonaduce
Donny Osmond has always had a bit of a squeaky clean image, so it's hard to imagine him throwing punches at another human being, but he did in 1994. That other human being happened to be former child actor Danny Bonaduce. Some say it's the greatest matchup in the history of celebrity boxing. It's certainly one that has been talked about in the decades that have passed since the two stars stepped into the ring.
So, who won? Bonaduce was officially declared the winner, but some say it was a close call. Osmond did his fair share of trash talk afterward, but what's important is that both men's charities of choice — the Tom and Roseanne Arnold Foundation and the Children's Miracle Network — both received generous donations.
(Image via Michael Schamis from New York, NY, USA, CC BY 2.0, via Wikimedia Commons; Rob DiCaterino, CC BY 2.0, via Wikimedia Commons)
Ruby Rose vs. Yi Sia
Most people know Ruby Rose as an actress, model, and TV host, but you can add celebrity boxer to her resume. Back in 2012, she stepped into the ring with boxer Yi Sia in an effort to raise money for charity. Sia had years of experience while Rose only trained for a few months.
Rose said she loved the experience, and that probably had something to do with the fact that she was the clear winner, winning every single round. The match happened to coincide with her first anniversary of being sober too, and she claimed she couldn't have done it if she were still drinking alcohol. Rose won money for the charity headspace, which is aimed at helping children with mental health issues.
Vanilla Ice vs. Todd Bridges
In 2002, the FOX network show "Celebrity Boxing" was pretty popular, and one of the biggest matches was between rapper Vanilla Ice, aka Rob Van Winkle, and actor Todd Bridges. Bridges, of course, played Willis Jackson on "Different Strokes." Both men had been quite popular in their day, but they'd since fallen away from the public eye. So, why not box each other to reinvent their careers?
In the end, Bridges won, though it was a close decision (30-27). Vanilla Ice had been the fan favorite, given that he'd trained with an MMA legend. But Bridges managed to knock him down a few times before they both disappeared back into obscurity. Ironically, as part of the same show, Danny Bonaduce returned to the ring, and this time, he took out former "Brady Bunch" star Barry Williams.
(Image via Rick Marshall, CC BY 2.0, via Wikimedia Commons; Rob DiCaterino, CC BY 2.0, via Wikimedia Commons)
Ricky Gervais vs. Grant Bovey
Ricky Gervais doesn't hold back with the celebrity jokes when he hosts awards shows like the Golden Globes and, as it turns out, verbal punches aren't the only type he throws. The comedian and actor has also tried his hand at boxing. In 2002, he stepped into the ring with businessman and TV personality Grant Bovey. The matchup was broadcast on BBC, and millions of people tuned in to watch.
After three rounds, Gervais was declared the winner, and money was donated to his charity of choice. The show was so popular that the BBC wanted to pair other celebrities for several other boxing matches, but there was also a bit of backlash from the professional boxing world. Professionals claimed that the match was dangerous and unlicensed, and if something had gone wrong, it could paint the entire sport in a negative light.
(Image via Thomas Atilla Lewis, CC BY-SA 2.0, via Wikimedia Commons; Danny Martindale/Getty Images Entertainment/Getty Images)
Jose Canseco vs. Danny Bonaduce
Obviously, Danny Bonaduce is something of a serial celebrity boxer, but he's not the only one. Former baseball great Jose Canseco, who is as known for his colorful personality as he is his ability to hit a home run, is also a serial celebrity boxer. So, it only makes sense that the two decided to duke it out in 2009. Up until then, Bonaduce had only boxed against other former child stars and won each match. Canseco had boxed against former football player Vai Sikahema and lost.
So, what happened when these two got together? The result was a draw. However, Canseco went on to keep boxing, winning matches against boxing pro Todd Poulton in 2009 and TV personality Tareq Salahi in 2011. A decade later, in 2021, he went up against Billy Football from Barstool Sports, but the former slugger lost that match.
(Image via Glenn Francis, CC BY-SA 4.0, via Wikimedia Commons; Rob DiCaterino, CC BY 2.0, via Wikimedia Commons)
Tonya Harding vs. Paula Jones
Tonya Harding is as famous for attempting to take out Nancy Kerrigan as she is for being a figure skater, so it may not be a stretch to imagine her boxing. She started out in 2002, training for the FOX network show "Celebrity Boxing" — the one that featured Vanilla Ice and Todd Bridges — and she boxed against former civil servant Paula Jones, or, as she's more famously known, the woman who sued Bill Clinton for sexual harassment.
Harding won the match and, in 2003, she decided to pursue boxing as a professional. No one knows exactly why she decided to take up the sport, although rumor has it that she was having money problems and needed the cash. Either way, she managed to win three matches and lose three before quitting completely due to problems with asthma.
Shaquille O'Neal vs. Shane Mosley
Shaquille O'Neal is one of the most famous basketball players to ever take to the court, and he's tried his hand at many careers and hobbies since retiring from the NBA. One of those just happens to be boxing. Well, let's back up. First, Shaq starred in his own show, "Shaq Vs," which, over the course of 10 episodes, showed the superstar going up against numerous challenges. One of those challenges happened to be professional boxer Shane "Sugar" Mosley.
The boxing match was more comedy than sport, according to most spectators. That may have had something to do with the fact that Shaq is 7 feet, 1 inch tall and Mosley is only 5 feet, 9 inches. Despite his height advantage, the former basketball champion lost the match.
Blac Chyna vs. Alysia Magen
Socialite and model Blac Chyna is one of the more recent celebrities to make her attempt at boxing. She stepped into the ring with fitness model Alysia Magen in June 2022, and both women managed to get in plenty of punches and trash talk before the pay-per-view match began.
In the end, Magen managed to knock Blac Chyna to the ground, and fans just knew she'd won. But the judges said otherwise. The match was officially considered a draw, but fans still believe otherwise. I think we need to see a rematch.
Dustin Diamond vs. Ron Palillo
Actor Dustin Diamond was best known for playing Screech on the hit show "Saved By the Bell." Unfortunately, his acting career seemed to end there, and he spent his years after the show attempting a standup career and appearing on multiple reality shows, including the FOX network's "Celebrity Boxing." Diamond went up against the actor Ron Palillo, known for portraying Horshack on "Welcome Back, Kotter."
Diamond won the match, but fans say it wasn't even a contest. Diamond was bigger, younger, and had more training. Sadly, both men have since passed away, but when their names come up, that boxing match is one memory fans haven't forgotten.
Chyna vs. Joey Buttafuoco
Most celebrity boxing matches pit a female against a female and a male against a male, but Chyna vs. Joey Buttafuoco is the exception to that rule. The pro wrestler went up against the body shop owner and tabloid mainstay as a part of the FOX network's "Celebrity Boxing" in 2002. Buttafuoco was originally supposed to go up against John Wayne Bobbitt, but Bobbitt had been arrested and couldn't take part in the match, so Chyna, aka Joanie Laurer, stepped in.
With her size and wrestling experience, you might assume that Chyna won the match, but judges declared Buttafuoco the winner. Scores were close, and fans were largely pulling for Chyna. So while the official record shows Buttafuoco as the winner, fans have Chyna as the winner in their hearts.
Aaron Carter vs. Lamar Odom
In 2021, former NBA player and reality star Lamar Odom and singer Aaron Carter stepped into the ring in New Jersey for their own version of celebrity boxing. Both men were coming off troubled pasts, so it seemed like a good idea to give them something else to work towards.
Odom is nearly a foot taller than Carter and about 65 pounds heavier than the singer, so right away, it didn't seem like a fair match. Once it began, it became quite obvious that Odom had the advantage. Carter could barely get in a punch. Things got so ugly that they didn't even make it to the third round.
Mitt Romney vs. Evander Holyfield
Finally, file this one under what the heck were they thinking? Former presidential candidate, governor, and senator Mitt Romeny was nearly 70 years old when he stepped into the ring with Evander Holyfield, one of the most notable professional boxers of all time.
If you watch the match, you'll notice right away that Holyfield didn't necessarily give it his all. Even so, he won the match. But the real winner was CharityVision, an organization that helps people who are visually impaired. It earned more than a million dollars.