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Ben Affleck -

Ben Affleck is a man of many talents. The actor, director, and writer also has a reputation for playing poker at amateur and professional level. 

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Ben Affleck - Of all the A-list poker players in Hollywood, Affleck is one of the best. He took home US$356,000 after winning a title at the California State Poker Championship in 2004. However, he has also been banned from several casinos for counting cards at the blackjack table!

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Matt Damon -

Matt Damon and Ben Affleck have been close friends and collaborators for decades. Another thing they share is their interest in gambling. Damon had always enjoyed visiting casinos and playing poker, but his game got a serious boost when he starred in the 1998 movie 'Rounders.' 

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Matt Damon -

Damon plays an expert gambler in the movie, and he was trained by legendary poker player Johnny Cahn to prepare for the role. He continued to use his new skills long after filming ended! 

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Edward Norton -

Edward Norton also starred in the movie 'Rounders' alongside Matt Damon, and he also developed his poker skills around that time. He's earned quite a name for himself in the celebrity poker world. Leonardo DiCaprio once auctioned off a poker game with Edward Norton as part of a charity fundraiser, and it sold for US$130,000.

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Brad Pitt -

Brad Pitt wasn't particularly interested in gambling until he scored a role in the 2001 movie 'Ocean's Eleven.' The plot centers around a casino heist and Pitt got into blackjack, poker, and slot machines to prepare for the role. 

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George Clooney - His 'Ocean's Eleven' co-star George Clooney has a totally different story. He has been playing poker since he was a teenager. Clooney went on to become a key figure in the private high stakes poker games that happen in the underbelly of Hollywood!

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George Clooney -

Clooney once even tried to invest in building his own casino. It was set to be built in Las Vegas and was going to be called Las Ramblas, but the plans fell through and he lost millions. That particular gamble didn't pay off. 

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Paris Hilton -

Socialite and heiress Paris Hilton is a Las Vegas regular, and reportedly loves to play casino games. It's said that she won US$30,000 on one particular trip.

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Paris Hilton -

It's rumored that Hilton also enjoys playing casino games online and on apps, but she does so anonymously. 

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Toby Maguire -

'Spider-Man' star Toby Maguire has been an avid poker player since he was a teenager. It's rumored that he lost a substantial amount of money to Ben Affleck in 2004, but that hasn't stopped him from playing. 

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Toby Maguire -

Maguire has taken part in several of Hollywood's elite private games, which were the inspiration for the 2017 movie 'Molly’s Game.' It tells the true story of a young female poker player who finds herself in trouble with the FBI. 

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Charlie Sheen - Charlie Sheen was a famous addict up until quite recently, and his extreme behaviors made headlines for decades. Gambling was another vice of his, and he used to love betting on sports. It's reported that at one point he was spending US$200,000 a week on gambling.

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Pamela Anderson -

Pamela Anderson is a fan of a little game of poker game every now and then. She's not at the professional level, however, quite the contrary. She's been known to lose US$250,000 in one night! 

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Floyd Mayweather - World champion boxer Floyd Mayweather has a history of making some outrageous sporting bets. He frequently bets hundreds of thousands of dollars on sporting events, and once even bet US$770,000 on himself!

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Michael Jordan - Michael Jordan is not quite as skilled at gambling as he is at basketball. He spends US$1 million on gambling each year. However, he can afford to lose it! 

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Gladys Knight -

The Empress of Soul used to hit the casinos in between performances in Las Vegas and Atlantic City, favoring blackjack or baccarat. Knight revealed in her autobiography that she struggled with a gambling addiction for years.  

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James Woods -

James Woods is said to be a cool customer at the poker table. The actor went to MIT with the intention of becoming an eye surgeon before pursuing a more creative career path, so there's no doubt he's got the brains. 

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James Woods -

Those who play with Woods say he has an uncanny ability to maintain a conversation during the game, distracting others but continuing to make calculated moves himself. 

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Michael Phelps - Olympic swimmer Michael Phelps used to have professional poker player Jeff Gross as his roommate, and he managed to pick up a trick or two! He's not a very active player but apparently he has the skills to go big.

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Tiger Woods -

Tiger Woods is extremely wealthy as one of the world's top professional golfers, but he also has a reputation for bad behavior. He's been known to lose US$25,000 in a single blackjack bet, and has been given a betting limit in certain casinos. 

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Brad Garrett -

Comedian and actor Brad Garrett is also a semi-active professional poker player. He was skilled enough to earn a seat on the show 'Poker Night in America,' and held his own pretty well. 

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50 Cent -

Rapper 50 Cent enjoys a game of poker or blackjack, but he's also made some impressive bets. He put US$2 million on Floyd Mayweather Jr. to win his fight against Manny Pacquiao, earning him a fortune! 

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Derren Brown -

Derren Brown is a famous magician, or mentalist as he prefers to be called, who has worked some of his magic in casinos. He was a professional blackjack and poker player and reportedly used his skills to guess his opponents' moves. 

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Gerard Piqué - Star footballer Gerard Piqué learned to play poker while he was with Manchester United. Since then, he has entered the World Series of Poker and the European Poker Tour, taking home around a quarter of a million US dollars.

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Jennifer Tilly -

Not only is Jennifer Tilly a legend of stage and screen, she's also a semi-professional poker player. She has taken part in the World Series of Poker and won the Ladies No-Limit Hold’em competition. She has earned around US$1 million in poker wins. 

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Shannon Elizabeth -

Shannon Elizabeth is another actress turned poker master. While she isn't a hardcore player, she has entered some major competitions and earned around a quarter of a million US dollars. 

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Charles Barkley -

NBA legend Charles Barkley amassed a large fortune during his career as a basketball player, and since his retirement he's been putting that money to work. Barkley is a regular poker player and is said to have earned huge sums at the card table since retiring. However, he also says he's lost around US$10 million at casinos! 

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Todd Philips -

Acclaimed director Todd Philips, know for his films 'Joker' (2019) and 'The Hangover' (2009), is another big Hollywood roller. He won US$250,000 in cash at the Legends of Poker event in 2005. 

Sources: (Celeb Mix) (The Logo Creative) (Card Player) (Best US Casino) (The Frisky)

See also: The most extravagant celebrity purchases

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