10 Celebrities Who Love Gambling

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Gambling is not uncommon among celebrities, be they actors, musicians, or business figures. But while some of them enjoy casino games now and then, others seem to dive deeper into this hobby. Here are top celebrities who love gambling that will most likely surprise you! 

1. Matt Damon 

Celebrities Who Love Gambling

The protagonist of "The Martian," Matt Damon, is famous not only among Hollywood celebrities but poker enthusiasts too. He is more than an amateur at this game, and he even made it to the finals of the World Series of Poker in 2019. The actor also played the role of a gambler who tries his luck at poker to help a friend in the movie "Rounders." 

Even if Damon didn't take part in poker shows with other celebrities, along with his fellow poker player Ben Affleck, they were seen at various luxury hotels enjoying private poker games. The actor's favorite poker game is Texas Hold 'em. 

2. Tobey Mcquire 

Tobey Mcquire, known chiefly for his role as a protagonist in "Spider-Man," also chooses to try his luck at poker every time he hits the casino. The actor plays poker against professionals in this industry and has a lot of good hands, according to his winnings. 

Mcquire won over $40 million from gambling in about four years. Even more than that, there are rumors that his talent at casino games served as inspiration for his role in "Molly's Game" as Player X. The actor loves poker so much that he chose to put his passion for this game over his acting career on several occasions. 

3. Ben Affleck 

Ben Affleck is right there with Matt Damon and Tobey Mcquire when it comes to his poker affinity. The protagonist of "Batman" enjoys casino games of all kinds, but if he had to choose a favorite, it would be by far poker. He even reached a top level in 2004 when he won the California State Poker Championship. 

The actor can be seen at top casinos, enjoying intense poker games against some of the most notable players. His favorite casino is the Las Vegas Strip. His gambling path was not always smooth. For instance, in 2014, Ben received a ban at Hard Rock for allegedly counting cards during a Blackjack game. 

4. Jennifer Tilly

Hollywood actress Jennifer Tilly received plenty of recognition in her movies but also at the poker table. The actress in "Bullets over Broadway" and "The Doors" took her acting career in parallel with her poker career, and she managed to shine in both. 

Tilly won the bracelet for the World Series of Poker in 2005, and in the same year, she had a resounding victory at the World Poker Tour (WPT) Ladies Invitational Tournament. According to the actress, she won over $1 million in earnings from poker tournaments. She got on the 29th spot in Aussie Millions 2019 and got up to four WSOP cashes. 

5. Drake 

The famous Canadian rapper Aubrey Drake Graham, known as Drake, is spotted frequently in famous Las Vegas casinos. The singer enjoys all kinds of gambling games, but his favorites seem to be Blackjack and poker. He enjoys exciting slot machines, too, and does not refrain from mentioning his gambling passion in his songs. 

However, if the rapper seems to be lucky when it comes to casino games, his luck only translates when he is trying it at sports betting. He lost over $2.5 million in 2022 in this industry, but that was not enough to make him quit. 

6. Charlie Sheen 

Charlie Sheen is not just a very beloved actor due to his roles in "Two And A Half Man" or "Major League", but also an avid gambler. The actor took the first page of major publications with both his acting career and his adventurous private life hobbies. He lost more than he won during some years and got luckier in others, but one thing is for sure: Sheen didn't give up his gambling aspirations. 

For Charlie Sheen, it seems to be more about the gambling experience than the winnings. When his $1 million player won the match, Charlie Sheen revealed to the New York Times that he felt nothing and he actually quit betting. 

7. Pamela Anderson

Pamela Anderson has quite an interesting bond with the gambling industry. While she didn't make an actual career in poker as she succeeded in Hollywood, the actress made an intimate confession on Wednesday's Ellen DeGeneres Show. She mentioned that she was $250,000 in debt as a result of a lost poker game, and she paid it with sexual favors. That is how she met her lover, the magician Antonio Esfandiari. 

The sexy actress became the image of a poker game online in 2012, 'BamPoker'. She doesn't seem to be as attached to other gambling games as she is to poker, but she definitely enjoys this industry as a source of entertainment. 

8. Tiger Woods

The man that comes to mind when we think about golf, Tiger Woods, is just as lucky when it comes to gambling as he is on the field. He has a betting limit at MGM Grand that reached $1 million and is known for winning with the same talent that he is losing. 

Woods prefers Blackjack with $25 thousand hands but also poker and other table games. Rumors are that Tiger Woods lost around $50 million to his gambling passion. But his net worth is less than it might seem. 

9. Aaron Paul

"Breaking Bad" actor Aaron Paul is no stranger to the gambling world. His game of choice is poker most of the time. The actor was part of the World Series of Poker in 2015. He also participated in Global Poker League's Summer Series Kickoff. Still, he never got the chance to test his gambling passion toward professional limits due to his acting career, which kept him fairly busy. 

The actor appeared in a commercial for Bet365 as part of the "Never Ordinary" campaign. His image was, therefore, associated with gambling all over the world as the ad went viral. 

10. 50 Cent

Curtis James Jackson, known as 50 Cent, is famous not only for his songs but also for his bets. The rapper enjoys sports betting quite often, and she is very proud of it. 50 Cent bets on all major sports, from boxing to football, and his investments get into the millions.

You can keep up with both his winnings and losses on his social media platforms, as he is very open about his gambling passion.


With impressive net worth, it’s not a shock that many celebrities choose to hit the fanciest casinos or try their luck at sports bets. And some of them even converted their gambling into a second career. It is all about the excitement and the entertainment vibe of this industry that keeps growing from one year to another. 

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