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Who Are Hollywood’s Biggest Gamblers? The Stars That Love the Vegas Strip


Hollywood is risky business, so it only makes sense that a lot of actors dabble in gambling.From movie stars and musicians to athletes and businesspeople, celebrities from all walks of life love games of chance. Some play socially or for sport, while others are downright addicted. And with so much money to burn, the stakes are pretty high.

There are some unexpected success stories and big losses alike going well into the millions. Even so, everybody comes back to the tables for the thrill. Here’s a rundown of some of the top celebrity gamblers and the stories which surround their games.

50 Cent

The first of our famous high rollers is hip hop megastar 50 Cent. 50 Cent was one of the biggest rap stars produced in the 2000s, gaining true exposure with hits like Candy Shop and In Da Club. Among his hidden talents is gambling. In 2011, 50 Cent won a whopping $500K through betting that the New York Giants would beat the San Fransisco 49ers in the2011 NFC Championship game.

They won 20-17, and 50 took to social media to flaunt the victory, posting photos of himself wearing cash like a scarf. He later tweeted out, ‘’I’m giving this money to my nana’’, predicting that she would likely faint. We love a family man! Still, if you thought he’d stop there, you’d be wrong. The following year, 50 bet that the Giants would take the New England Patriots in Super Bowl XLVI. The team pulled off a 21-17 victory, and 50 won a cool million.

Charlie Sheen

The entertainment industry has evolved a lot over the years. Still, Charlie Sheen stands as the most authentic picture of Hollywood hedonism. Amongst his notorious vices: gambling.

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In fact, during his 2006 divorce from Denise Richards, documents revealed that Sheen had spent about $200,000 per week on his daily sports gambling.

Six years later, in an interview with the New York Times, Sheen revealed that his biggest bet was on a boxing match between Manny Pacquiao and Oscar De La Hoya, after he had a dream predicting the results. Though Sheen took home a million dollars, he stated that he ‘’felt nothing.

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’’ Thankfully, he and now considers himself a retired gambler.

Ben Affleck

For anybody who’s ever seen the movie Molly’s Game, Ben Affleck’s appearance on this list should be no surprise. For those who are unfamiliar, the film is based off the true story of a celebrity underground poker empire – which Affleck was known to frequent. According to those who have seen him in action, he could have been a successful poker player – and if you’d like to follow his footsteps, you can dive into online poker games and advance your skills.

Ben has been tutored by two professional poker players – Annie Duke and Amir Vahedi, and played at both amateur and professional levels. The biggest hand he’s ever won in one single session was 800k. The actor has also been known for his penchant for Texas Hold’em, Omaha, and Blackjack – though unfortunately, he was banned from a lot of casinos for counting cards in the past.

Matt Damon

So, as it turns out, birds of a feather flock together. Over the years, Matt Damon has worked on nine movies with Ben Affleck – and shares the same love for high stakes gambling. Though he always liked gambling, this interest really took off when he was cast for a leading role in the 1998 poker-inspired movie Rounders.

To prepare for the gig, Damon was trained by world-renowned professional poker player Johnny Chan. He still likes to play whenever he has the time, and is known to have participated in a variety of tournaments. The actor has played the World Series of Poker a few times, as well as the Ante Up for Africa, where all the proceeds go to charity.

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Still, if you’re looking to lay a bet, Damon can be spotted at some of the world’s finest casinos. He, Affleck, and George Clooney even have an annual tradition:that is, one week of gambling in Vegas.

Paris Hilton

Cast your mind back to a different time. The year is 2003, and Paris Hilton’s homemade sex tape just broke. One small detail many may not recall is that Paris’ then-boyfriend and infamous sex tape counterpart Rick Salomon was actually a successful professional poker player. Oh, the things we could have picked up on if we’d just paid attention more. Needless to say, we’re learning more and more about Paris Hilton each day.

Allegedly, the heiress has been playing poker since her teenage years, and has developed quite the skill for it. At age nineteen, she made headlines after being clocked with Leonardo DiCaprio at the tables. Since then, she’s had many big wins, including one blackjack victory of $50,000, and another of $30,000 at her 31st birthday party. We like to imagine that the carefully cultivated Simple Life persona only helped her to trick opponents. Hey, it worked on us!


We hope you enjoyed our rundown of some of Hollywood’s biggest gamblers. Still, gambling is not exclusively for the masses. Whether you’re looking to improve your strategy, or make a big win, you can enjoy all the games that celebrities play online.

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