25 Celebrities Who Endured Embarrassing Sports Failures

24. Nate Robinson

Former NBA star Robinson’s career is most noteworthy for his success in the NBA Slam Dunk Contest. The former New York Knicks star was an explosive leaper and won the competition three times. However, he was under the mistaken belief that because he was an elite athlete, he was capable of being competitive in any sport. Unfortunately, this wasn’t true as he discovered in his professional boxing debut in 2020.

Robinson fought YouTube star Jake Paul on the undercard of Mike Tyson’s comeback exhibition match against Roy Jones Jr. The former NBA star suffered a brutal knockout as he failed to show his skills. After the fight, boxing fans, analysts, and combat sports athletes slammed the Californian State Athletic Commission for sanctioning the fight. Combat sports is not a game.

23. George Clooney

Everybody knows Clooney as one of the most famous actors of his generation. The star of the Oceans Eleven franchise as well as countless other movies, Clooney is also a proficient director. As a youngster, Clooney was a talented high school baseball player. His excellence resulted in the Cincinnati Reds offering him a trial. Clooney accepted and went to the Queen City in a bid to follow his MLB dream.

Unfortunately, he failed to impress and they didn’t offer him a contract. Of course, ‘unfortunately’ is used loosely in this context, because Clooney enjoyed far greater success than he could ever have dreamt of when he became an actor. His net worth is an estimated $500 million. It’s funny to imagine how different somebody’s life could have been if there was the slightest change in circumstances.

22. Kurt Russell

A star in films like The Hateful Eight, Once Upon a Time in Hollywood, Guardians of the Galaxy Vol. 2, and many others, Russell is one of the most popular actors of his generation. The Massachusetts-born actor constantly appears on the big screen but that wasn’t even his initial dream. Russell was a talented baseball player and came incredibly close to making it to the MLB. It wasn’t his ability but instead his body that caused him to miss out.

The California Angels signed him as a second baseman in 1971. He then played for four of their minor league affiliates and also won an All-Star award in his rookie year. In 1973, he led the Texas League with a .563 batting average in his first 16 at-bats. This was good enough for the Angels to call him up to play in the Major League. However, a torn rotator cuff ensured that he failed to fulfill his dream – at least in a sporting sense.

21. Brock Lesnar

Lesnar’s appearance on this list may seem strange because of his history as a UFC champion and one of the biggest names in professional wrestling. He also tried to pursue a career in football. However, he failed in this pursuit because the Minnesota Vikings didn’t want him. After WrestleMania XX in 2005, he impressed the Vikings at the NFL combine and signed a contract.

But he only spent a month with the team before they decided to cut ties with him. Lesnar clearly loves concussions because he seems to love sports where they frequently happen. In hindsight, he won’t care because he became one of the most marketable figures in sports entertainment and made millions of dollars throughout his career there. In the end, a groin injury, a result of a motorcycle accident, ended his dream of playing in the NFL.

20. Andrew Flintoff

‘Freddie,’ as British cricket fans affectionately know him, was one of the best cricketers on the planet up until his retirement in 2015. He was also one of England’s most important players and featured in events like the World Cup and the Ashes. But after retiring, he made the unexpected decision to transition to boxing. While they’re obviously both sports, cricket and boxing don’t have an obvious connection.

He fought Richard Dawson in a heavyweight boxing match at the Manchester Arena in front of thousands of fans. While he won his first professional bout, Dawson dropped him in the fourth round. Furthermore, the American boxer definitely wasn’t a household name. In the end, Flintoff admitted that he had failed to show he could make a substantial career as a pro boxer and quit after a single fight.

19. Gordon Ramsay

One of the most famous celebrity chefs on the planet, Ramsay is notorious for his foul language and harsh opinions. But that’s also why he’s so entertaining. Meanwhile, Ramsay also dreamed of pursuing a career in soccer when he was a youngster. The Glasgow-born chef went on trial at Rangers but failed to make the grade. However, he still loves the club until this day.

Furthermore, he did receive the chance to play against the pros in a Soccer Aid game back in 2012. Former England international Teddy Sheringham even gave him bruises to remember the game by. Sheringham smashed Ramsay with a crushing tackle and then patronizingly patted him on the cheek. In obvious discomfort, Ramsay maintained his smile to his credit, but he definitely felt that one.

18. Kevin Connolly

Russell Wilson is one of the best quarterbacks in the NFL. The Seattle Seahawks signal-caller inadvertently caused Connolly a lot of pain when the pair filmed alongside each other for HBO’s Entourage TV series. In the scene, Connolly caught one of Wilson’s passes. This is an important detail because there was no direct bodily contact between the two men, so there was no real excuse for what happened next.

Somehow, as Connolly caught the ball, he stumbled and awkwardly jarred his leg. It resulted in it actually breaking and doctors ended up putting him in a plaster cast. This definitely wasn’t the scene that the American star expected when he signed up. However, he continued filming like a trooper and earned Wilson’s respect. He failed to make an impression with his skills and his injury rated as a top sports failure.

17. Charles Barkley

A brilliant basketball power forward, Barkley was one of the most popular NBA players around during his heyday. However, as previously discussed, being a great athlete doesn’t automatically translate to excellence in other sports. An 11-time All-Star, Barkley was excellent on the basketball court but not as good on the golf course despite his determination and love for the gentleman’s game.

Barkley regularly competed in games and even featured in events like ‘The Match.’ But there was no disguising his awful swing, which was so bad it was brilliant. It’s just as well that he didn’t rely on golf for money, because he would have suffered bankruptcy quicker than an NBA star. Still, there is almost something to admire in his herky-jerky swinging style. He never failed to entertain nonetheless.

16. Tony Danza

The Emmy and Golden Globe-nominated TV personality and actor was a fixture on TV screens throughout the 2000s. From 2004 to 2006, he had his own talk show. On one segment he raced against former NASCAR driver Rusty Wallace. The pair drove go-karts around a track and things went badly wrong for the media personality because he almost died.

He was actually in the lead by a narrow margin before Wallace bumped him with his car. Then Danza spun out of control and his car flipped over. Spectators expected the worst, but luckily he was alright apart from a nasty concussion. Danza failed in his effort to beat a professional race car driver, but at least he crashed out in style. In the end, he was happy to survive what could have been a tragic accident.

15. CM Punk

Phil Brooks, better known by his former pro-wrestling nickname CM Punk, had a huge fanbase during his time with the WWE. Then he created waves by following in Brock Lesnar’s huge footsteps and joining the UFC. The MMA promotion thought that they had a potential pay-per-view star on their hands while fans were curious about Punk’s skills against real fighters. Ultimately, every aspect of this project failed.

Punk had two UFC fights. First of all, Mickey Gall battered him in his Octagon debut. Then, Mike Jackson repeated the same feat. The former wrestler had no obvious athletic advantages over either of his opponents and suffered a lot of damage. Furthermore, the UFC didn’t receive the wave of casual wrestling fans they had hoped for either. It was an unmitigated disaster.

14. Dwayne Johnson

It should come as no surprise, but ‘The Rock’ was an excellent NCAA football player. He was even a part of the Miami Hurricanes’ 1991 championship win. However, the defensive tackle suffered a bad knee injury at the worst possible time. The team then replaced him with future NFL star Warren Sapp. But this had serious consequences for his potential career as a professional football player.

NFL teams didn’t draft him because of injury doubts. After this, he signed a contract with the Calgary Stampeders in Canada, but they released him after two months. Of course, he emerged as one of the biggest stars in WWE before becoming the highest-paid actor on Forbes’ rich list in 2020. Things definitely didn’t end badly for Johnson, who must now count his blessings that his football career failed.

13. Garth Brooks

The Country Western star is a massive baseball fan. Furthermore, the Country and Western Hall of Famer even tried to make a career in the sport. Between 1999 and 2004, he signed several Minor League contracts and also attended MLB spring training sessions. The latter saw the Padres, Mets, and Royals invite him along in order to raise awareness for his charity, but he failed to make an actual impression on the field.

In three spring ventures, he achieved just three hits. Brooks adored baseball. Because he was a massive celebrity, he was able to secure annual invitations to these teams. One has to wonder what the professionals made of his vanity project because he wasn’t very good at the game. However, he has sold more albums than anybody else in the United States, so he can do what he wants.

12. Conor McGregor

The biggest star in MMA, McGregor was a two-weight UFC champion. Renowned for his brash trash talk, knockout power, and volatile personality, the Irishman is also one of the richest athletes in the world. However, as good as he is in the cage, he’s not as brilliant when it comes to other sports. In 2018, the Dallas Cowboys faced the Jacksonville Jaguars with McGregor present as the guest of honor.

Worse pass thrown in the state of Texas today…Nathan Peterman's pick six or this effort from Conor McGregor? 🤔 pic.twitter.com/Zcxz4132V3

— LastWordOnNFL (@LastWordOnNFL) October 14, 2018

He definitely enjoyed himself as he hyped the team up in the huddle and got into the football feeling. Unfortunately, it all went downhill from there because he totally failed in his attempt to throw a football. Social media is not a kind place and annihilated McGregor for his shoddy effort. He has a powerful left hand, but nobody will be calling him up at quarterback anytime in the near future.

11. Boris Johnson

The Prime Minister of the United Kingdom is no stranger to gaffes in daily life or on the sports field. In 2015, the then-Mayor of London visited Tokyo in an official capacity. Aware of his love for rugby, organizers invited Johnson to attend a street rugby practice. Johnson eagerly agreed to participate and demonstrated bullish enthusiasm. However, one child named Toki Sekiguchi, is probably still concussed as a result of Johnson’s involvement.

Johnson carried the ball like a rampaging rhinoceros. Japanese spectators roared with appreciation as the politician lumbered down the touchline. Then he literally bulldozed into poor little Sekiguchi, flattening the child. His coach also failed to show any sympathy to the boy as he dragged him away out of the spotlight to pretend it didn’t happen.

10. Mariah Carey

Carey joins the ranks of terrible celebrity first-pitchers with this attempt from 2011. She attended a game between the Yomiuri Giants and the Rakuten Eagles in the famous Tokyo Dome. As one of the greatest female artists of the 1990s, she was a global superstar. Japanese fans were very excited to watch her throw the first ball of the day in the Nippon Baseball showdown, yet it wasn’t worth the wait.

Ever the diva, Carey looked the part with her giant sunglasses, short skirt, and heels. None of these items were conducive to baseball because she created a failure with her pitching attempt. It was a feeble throw and she was happy to escape from the field. Nobody expected her to throw a 90 mph pitch, but if hers was any slower, it would have gone backward. Stick to the day job, she made untold millions at it.

9. Stephen A. Smith

With his loud, outspoken criticism, Smith has attracted a ton of attention during his time as a sports analyst. Since ESPN obtained the rights to UFC events, his breakdowns have become a regular feature. However, many UFC fighters dislike Smith for the way he speaks about them. This is because they think that he doesn’t understand the sport or appreciate the dangers and complexities of fighting.

Needless to say, they weren’t kind when Smith posted a video of himself hitting pads. Anybody who tries out combat sports deserves a certain level of respect, but after Smith’s comments, the schadenfreude was rife. His form was more reminiscent of an animated mannequin than an actual boxer. Combat sports athletes unanimously agreed that Smith failed to impress with his display. Sometimes it’s best to stay quiet.

8. Boris Johnson

The second installment of Johnson’s sports failures, this one looks even more painful than the first. Before his time as PM of the UK, ‘BoJo’ enjoyed a ton of public goodwill. Many people appreciated his blustering manner of speech, his unkempt appearance, and his capacity for a blunder always made him entertaining. It also meant that he attended many kinds of celebrity events including this charity soccer game.

England played Germany in a spoof recreation of the classic 1966 game. It featured a combination of retired professionals and celebrities. However, the highlight-reel moment was when Johnson ran head-first into Maurizio Gaudino’s groin. The former German international crashed to the ground in pain as Johnson attempted to jog away with an innocent expression on his face that failed to convince anybody.

7. Will Smith

We’re not entirely sure what happened here. Smith was in London with his son Jaden to promote his new movie After Earth. While in the UK capital, the Smiths had the opportunity to hang out with some massive soccer names like Luis Figo and Edwin Van der Saar. They even took penalty kicks against the famous Dutch goalkeeper but the elder Smith’s was so bad that it’s unbelievable.

He failed to get any power on his first shot. Sure, he was having fun and it wasn’t serious at all, but it’s still remarkable that a man with his physique couldn’t kick a ball at all. Then Jaden took a shot and scored, although his father lifted the goalkeeper out of the way. The only thing worse than that penalty kick was the movie because at least the former made people laugh.

6. P. Diddy

Jamie Foxx was iconic as quarterback Willie Beaman in the Oliver Stone movie ‘Any Given Sunday.’ It should come as no surprise that Foxx was so good in the role because he was a genuinely talented ballplayer. He became the first QB in his high school to rush for over 1,000 yards and also dreamed of playing for the Dallas Cowboys. But he wasn’t even Stone’s first pick for the role. That was P. Diddy.

The rapper claimed that scheduling conflicts forced him to leave the film at the last minute. However, rumors quickly circulated that he couldn’t throw a ball to save his life. Allegedly, Diddy’s throwing mechanics were shockingly poor, and no amount of coaching could help him. Stone and the casting director had a tough decision to make, but in the end, they chose the right man for the job.

5. Carly Rae Jepsen

The Canadian popstar rose to prominence in 2012 for her single ‘Call Me Maybe.’ However, Jepsen’s manager won’t expect any phone calls from MLB franchises after one of the worst celebrity first pitches in the history of humankind. Jepsen has many talents, but baseball definitely isn’t one of them. Tampa invited her to throw the first pitch at Tropicana Stadium before their game against the Houston Astros.

Jepsen stood there in her short shorts with her Rays’ jersey knotted above them. She wound up but held onto the ball for too long and ended up just dropping it in front of her as she failed. To be fair, she was a good sport about it. Jepsen might throw wishes in wells but she wouldn’t hit the ground if she fell out of a plane. It could have been worse but we’re not exactly sure how.

4. Logan Paul

Paul is a leading YouTube star with millions of social media followers. He also has a reputation for being a moron with one video in Japan attracting massive controversy because he filmed a dead person in a forest. Meanwhile, Paul and his younger brother Jake have recently stepped into the world of professional boxing. He fought fellow YouTuber KSI in an amateur match that went to a draw. Then they agreed to rematch as professionals.

However, this didn’t go as well as Paul expected because he lost the match. It was controversial because the referee deducted two points from him in the final round. But it was still embarrassing for the Internet star because he talked himself up so big. He wanted to win so that he could continue to run his big mouth and annoy the entire world. Now his brother is the one doing that instead.

3. 50 Cent

50 Cent has sold over 30 million albums throughout his career but don’t ask him to pitch a baseball. This might seem like a strange connection but the rap icon joined the ranks of terrible celebrity pitchers in 2014. This infamous moment took place before the Mets-Pirates game at Citi Field. No doubt the hip hop legend had visions of going full Babe Ruth in front of the watching fans.

To make matters worse, his practice throws weren’t bad at all. Unfortunately, he clearly isn’t reliable in clutch situations because when the time came, he totally failed. The run-up looked good and he winded up his arm, but then he blasted the ball so far wide-left that it probably came back to hit him. As one YouTube fan commented, “his aim is so bad, he probably shot himself those nine times.”

2. Jose Canseco

Canseco is a colorful character who made his name as an MLB star. A two-time World Series winner, he was also the AL MVP in 1988. But Canseco totally tarnished his record when he openly admitted to using performance-enhancing drugs throughout his career. After retiring from baseball, he decided to transition to MMA. However, that didn’t work out very well for him.

He competed against giant cult hero Hong-Man Choi during the Super Hulk Grand Prix at DREAM 9. The event took place in Japan where they love a freak fight. It went about as well for Canseco as he could have expected because Choi demolished him in under one round. Freakishly tall and strong, Choi used his reach and power to bully the former baseball star and forced him to tap out.

1. Diana Ross

The World Cup is the most-watched sports tournament on the planet. Every four years, soccer teams from every continent battle it out to prove that they’re the best. The USA hosted the tournament in 1994 because the geniuses at FIFA thought that would make Americans care about that sport. However, that worked as well as Icarus’s wings because it totally failed. But one moment is emblematic of the US’s relationship with soccer more than any other.

Oprah Winfrey fell off the stage after introducing Ross at the opening ceremony. Then the Supremes’ star performed before one of the most cringe-inducing moments in sports history. Next, she took a penalty to symbolically open the tournament. Ross ran up in her dress and heels before smacking the ball wide of the goal. But the organizers rigged the net to split apart regardless. It was hilariously bad.