Celebrities Who Admit To Being Big Sports Gamblers

While there are obvious ways celebrities live differently than the rest of us, their interests — or in some circumstances, addictions — can inform us as to how we are similar. According to a September 2022 Pew Research Center survey, 19% of American adults wagered on sports bets that year. Fast forward to 2024 and Super Bowl LVIII, and you'll find that a record 67.8 million Americans bet on the big game, representing 26% of adults, as reported by the American Gaming Association. This should give you some idea of how sports betting impacts the U.S. economy today, and there's no reason to believe celebrities aren't getting in on some of that action.

The reasons celebrities gamble are similar to why regular people place bets as well. They can be opportunities to socialize with other people who share their interests, to manage their stress by taking their minds off personal or professional matters, or just for fun and entertainment. That being said, there is also a dark side to sports betting, specifically, problem gambling, which at least one of the following celebrities admits to.

Charlie Sheen is known for his roles in '80s films like "Wall Street" and most recently, the co-star of the successful but long canceled "Two and a Half Men" TV series. He survived a rough patch of sex, drug, and alcohol addiction back in 2011 that included incoherent rantings, his eventual termination from "Two and a Half Men" for insults hurled at the co-creator, and his general erratic behavior. He's since apparently become apologetic for his past behaviors under the influence, blaming the pressures of co-starring in the successful show and navigating the dissolution of two marriages as catalysts for his addictions.

Yet, even before that period, his ex-wife Denise Richards noted Sheen's sports gambling as a factor in her seeking divorce. The actor was reportedly betting $200,000 per week, and it was said to result in unhinged outbursts whenever he lost. In a 2012 interview with The New York Times, Sheen said he bet $1 million on a boxing match between Manny Pacquiao and Oscar De La Hoya, and he won. However, after winning, he said he failed to get the rush he expected. As Sheen said, "I felt nothing. And I went, O.K., there's nothing left for me here. Unless my children are involved in the wager, no sense in making it, you know?"

While Ashton Kutcher's film catalog may be a roller coaster of wins and losses, he appears to excel in the world of sports betting — mainly on college football. Kutcher has spun his career as an actor into a side career as a venture capitalist with his investment arm Sound Ventures LLC, which raised $243 million in five weeks to fund investments in tech companies. He brings this scientific thinking to his betting strategy, which involves a lot of math used to discover numerical anomalies.

Kutcher's betting skills were so good, he was allegedly sought after by professional sports bettor Billy Walters, who claimed one of the biggest sports betting wins of all time and also began his own illegal sports betting syndicate (ACME Group Trading) in Las Vegas. Walters used a system of algorithms and probabilities to place bets through intermediaries with code names like "the Reader" and "The Wolfman," the latter of whom Kutcher and two other high-profile celebrities are suspected of being. By Ashton Kutcher's own admission in an interview with Esquire, he did place bets for a national sports betting syndicate, for which he won $750,000 in four weeks for wagers placed on college football. The bookmakers believed they had a patsy celebrity and paid for it in the end.

Rapper, producer, and Cash Money records founder Bryan "Birdman" Williams has made a lot of cash money — an estimated $150 million — over his career. And he doesn't seem to have a problem losing some of it to his sports bets. While by no means one of the biggest losses in gambling history, Birdman did watch $2 million of his net worth fly away after a bet on the Miami Heat to win the NBA championship in 2011, which didn't pan out.

Unlike Ashton Kutcher, Birdman seems to prefer a less mathematical approach to placing his bets. He instead relies on his gut, which he did in 2012 before bragging on the social platform X (via CBS News) about taking a $5 million stake on the New England Patriots to beat the New York Giants in Super Bowl XLVI. As football fans would know, the Giants won, and while there's no confirmation if Birdman made good on his proclaimed wager or not, we do know he would've lost $5 million in the process if he did.

Birdman has had some big wins, however, including $1 million from a $4 million bet on Floyd Mayweather to beat Shane Mosley in 2010. (Birdman then followed this up by vowing he'd bet $10 million on Mayweather to beat Manny Pacquiao whenever the two next met in the ring.) He also scooped up another million when Green Bay beat Pittsburgh in Super Bowl XLV.

Rapper and mogul Curtis "50 Cent" Jackson has been candid, both in interviews and in his music, about betting on sports. As reported by The Bleacher Report in 2012, 50 Cent once posted on X, in a now-deleted post, that he listens to the voices in his head on what to bet and on which team. In the case of the NFC Championship game that year between the San Francisco 49ers and the New York Giants, he won $500,000 by betting on the underdog Giants — because the voices told him to bet "GIANTS."

The rapper also wagers on boxing. As with the aforementioned Birdman, 50 Cent also bet on Floyd Mayweather to beat Manny Pacquiao back in 2015, placing a $1.6 million wager on Mayweather and telling a radio station at the time that Mayweather couldn't lose, per Sports Illustrated. Said 50 Cent, "He can't lose," as was posted on X at the time in May. Sports Illustrated also pointed out that for the match, 50 Cent switched to Mayweather after saying just three months earlier that Mayweather was "scared to death" to fight Pacquiao.

Ben Affleck is no doubt the highest-profile celebrity on our list, and his dedication to gambling in general can be seen in his "all in" attempt to learn to count cards in blackjack, which ultimately got him banned from the Hard Rock Casino in Las Vegas back in 2014, according to the Los Angeles Times. (And on that note, here's how casinos actually catch card counters.)

In a 2021 interview with Complex, Affleck talked about how his father introduced him to sports betting with a book of sports bets on teams he put together in his bar. For Affleck, betting made the games more interesting, saying, "So sports betting has always, to me, been part of the fabric and culture around my life. It's always kind of been an aspect of watching sports that frankly makes it more fun. If you have $50 on the game and you're watching, like me growing up when the Patriots were terrible and the Red Sox were terrible, the Celtics were good for a minute, watching those teams it made it more interesting if you had $50 on the game."

The actor's love of sports betting turned into a collaboration with WynnBET in 2021, where he showed his support for the online sports betting and iGaming app by directing three ads, starring himself, Shaquille O'Neal, and comedian Melvin Gregg.