Most Notorious Gamblers in Hollywood

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Posted: February 27, 2022

Updated: February 27, 2022

  • Lots of Hollywood star enjoy gambling and visit casinos regularly
  • Charlie Sheen has been one of the most notorious gambler
  • Ben Affleck was banned from casinos due to card counting

Gambling is a popular activity in the film industry as well, with several famous actors and actresses taking part in it. Most of them love poker and even take part in special competitions. While others spend huge amounts of money on sports betting. From Tobey Maguire to Charlie Sheen, let’s see the most notorious gamblers in Hollywood. 

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Hollywood is the home of all kinds of stars from the entertainment industry, who are all very famous and rich. It’s not surprising that many of them spend lots of money on gambling, and visit casinos regularly. They are often invited by casinos as well for new openings or special events to increase their popularity. With some of them enjoying these appearances a lot more than others. While other Hollywood stars prefer private poker rooms where they can hide from the world. The following celebrities are all known about their gambling addiction, with some of them being bad losers as well. 

Charlie Sheen Is One of the Most Notorious Gamblers in Hollywood

Charlie Sheen, the actor of Two and a Half Men, Major League, and several other comedies has a bad reputation in Hollywood. He is said to be an alcoholic, drug user, and gambling addict. He used to spend hundreds of thousands of dollars on sports betting in a single week according to his ex-wife, Denise Richards. The actor is also known as a bad loser who often lost his temper after losing a bet. But even a huge win following a successful boxing bet didn’t lift his mood. Sheen also started his own gambling site but he stopped betting himself. Well, it’s hard to believe it from one of the most notorious gamblers in Hollywood. But who knows, maybe he really quit gambling and just does it in his films now. 

Tobey Maguire, the Bad Loser

Tobey Maguire usually plays nice characters in his films, but in real life, the actor can behave quite badly. Especially during gambling.  Maguire took part in high-stake private poker games, as we mentioned here before. But he couldn’t handle losing and was rude most of the time.

most notorious gamblers in Hollywood
Picture Source: Wikimedia Commons

At the same time, he was also taking part in professional poker tournaments and won over $10 million in them. It looks like his teacher, Canadian top player, Daniel Negreanu did a good job. In 2011 though Maguire had to settle a lawsuit following his involvement in illegal high-poker games. Since then we haven’t heard much about his gambling habits. But If you’d like to play poker, you can do it legally on online poker sites in the US. 

Walther Matthau Was a Huge Fan of Sports Betting 

Casinos have attracted film stars in earlier decades as well. One of these actors was Walter Matthau who couldn’t resist throwing the dice at the craps table. While he also loved sports betting and spend big amounts on various events. Betting on basketball and horse racing were his favorites, but one time he spent $183,000 on a spring training baseball game.

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The Odd Couple and Grumpy Old Men actor was said to spend more than  $50 million on gambling. Even the back of his funeral list contained horse betting tips. Despite cutting down on gambling after a heart attack in the 1970s, looked like he couldn’t resist sports betting entirely. 

Famous Gambling Actresses: Pamela Anderson and Jennifer Tilly

Of course, gambling is not limited to men, famous actresses can also become addicted to it. Like Baywatch star Pamela Anderson, who has been playing poker regularly and losing significant money with it. In one game she ended up $250,000 down and ended up marrying the guy she owned the money.

most notorious gamblers in Hollywood
Picture Source: Wikimedia Commons

Well, it might be even true as Anderson married poker player Rick Salomon in 2007 but they divorced after 8 years of marriage. Another Hollywood actress, Jennifer Tilly has been much more successful at the poker table. She even won the Ladies No-Limit Texas Hold’em event at the World Series of Poker tournament in 2005. If you want to follow her steps, get some practice and play poker on one of the online gambling sites in the US. 

Ben Affleck Was Banned From Casinos

Another famous gambler from Hollywood is Ben Affleck who has been even banned from Hard Rock Casino premises in 2014. Apparently he counted the cards at the blackjack table which is not welcomed in casinos though it’s technically not illegal. The actor said that he didn’t use any electric service, just has a good memory and great skills.

His confession didn’t impress casinos though. Affleck also loves baccarat and poker, he has even won the California State Poker Championship in 2004. The Oscar-winning actor took part in private poker-games too along with Maguire and DiCaprio. While last year he organized a celebrity poker tournament and raised over 1.7 million dollars for a charity. His best friend, Matt Damon also took part in it who is a big poker fan himself. But he is known as a nice guy in the poker circle unlike some of his colleagues.  

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