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Famous Celebrities That Have Had Bad Gambling Habits


Celebrities are often spotted in the big casinos of Las Vegas or Atlantic City spending hundreds of thousands of dollars without batting an eyelash. They are used to being the center of attention, they like to take risks and they are used to success. So why not, right? As long as they don’t go overboard and get into huge debts there is no harm done in a little bit of gameplay here and there.

In this article, we are going to tell you about top athletes and Hollywood stars who play casino games and are the most likely to be spotted at the poker, blackjack or roulette tables.

Ben Affleck


Ben Affleck who starred alongside Justin Timberlake in the movie Runner, Runner which is about the underworld of online gambling in Costa Rica, is in real life a big-time gambler. Affleck’s passion is blackjack and poker and he is known for huge bets on these card games. In 2001 he lost $400,000 on a hand of poker and as far as we know this has been his biggest one-time loss. In 2004 the movie star won $350,000 in a poker tournament. He spends a lot of time in different Las Vegas casinos and he is actually banned from the Hard Rock casino because he has been caught once counting cards.

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Charlie Sheen


Most people have heard of Charlie Sheen’s cocaine addiction but many are not aware that the movie star is also a compulsive gambler. He plays poker and bets on different sports and he is said to spend hundreds of thousands of dollars every month in casinos. His biggest loss was $1 million.

Michael Jordan


Michael Jordan is the fourth richest African American and the only billionaire in NBA history. The ex-basketball star might be able to afford his losses but it is rumoured that his retirement was because of suspension by the basketball league for gambling. He has lost hundreds of thousands of dollars in casinos, but he also takes betting to the golf course where he plays against other celebrities and athletes and bets on beating them. Jordan lost $1.25 million against Richard Esquinas one time on the course.

Ashton Kutcher


Kutcher’s passion is sports betting and in particular college football. Ashton used to be the face of the USA’s biggest sports betting syndicate who are essentially professional sports bettors. The actor placed huge bets on their behalf on college football and managed to cash in $750,000 in a four-week period. The unsuspecting casinos didn’t take Ashton for a professional – and those kinds of bettors are not welcome in Las Vegas casinos.

Tiger Woods


Tiger Woods is considered the best golf player of all times and with his net worth of around $900 million he can afford to lose some money here and there. Woods’ favourite game is high-stakes blackjack and he is known to have placed $250,000 bets per hand. He is often seen in Las Vegas casinos with one lady companion or another and allegedly a certain Las Vegas casino has even set a $1 million betting limit for him.

Tobey Maguire


You might only think of Spiderman as a hero but unfortunately, he has a number of bad habits. He is said to have a drinking problem and he is a compulsive poker player. He once participated in an illegal poker party at a Beverly Hills mansion and faced a lawsuit for it later. It is rumoured that at the poker party the buy-in was $100,000. We don’t know how much he was suid for so we are not sure if the party was worth it.

Matt Damon


Matt Damon is one of those movie stars who play poker. He regularly visits casinos and he is actually quite good at the game. He usually doesn’t place high stake bets so he seems to be in control of his gambling habit; moreover, he very often wins. He is a regular at Las Vegas casinos just like his gambling and actor friend Ben Affleck.

Jenifer Tilly


You might have seen Jennifer in The Fabulous Baker Boys or the Bride of Chucky. The Academy Award nominee actress is a successful poker player. She participated in the World Series of Poker in 2005 and went home $160,000 richer. She is considered a professional poker player and also appeared on the cover of the Card Player Magazine.

50 Cent


The famous rapper knows his business around sports betting. He won $1 million on a well-placed bet on a fight between Floyd Mayweather and Oscar de la Hoya. His other most significant win was $500,000. 50 Cent then bet on an NFC Championship Game between the Giants and the 49ers in 2012.

Michael Phelps


The former competitive swimmer spends lots of time on casinos’ floors. He is said to have lost a great amount of money in poker games. The former athlete also has a problem with alcohol and has been arrested more than once for driving under influence.

Tomas Brolin


Tomas Brolin might not be so well known outside of Sweden, but the former Swedish football star is a very successful poker player. He came 38th in Monte Carlo at the EPT Grand Final. He also participated in several European Poker Tours.


If you want to spot Hollywood stars, hanging out at Las Vegas casinos is not such a bad idea. As the list about shows, there are plenty of actors, sportsmen and musicians who love to gamble and they usually do it for high stakes!

Written by Marinelle Adams