High Roller Celebrities that Love to Gamble

Gambling is a popular pastime enjoyed by many people from different walks of life, including celebrities. The glitz, glamour, and excitement of casinos have always been alluring for the big names, and many are often seen at the high-stakes tables in VIP rooms. Besides having a huge bankroll to play with, some celebrities are known to have excellent gambling skills that even rival professional players. 

That said, this article takes a look at some famous high-roller celebrities who enjoy high-stakes gambling and are pretty good at it. 

Ben Affleck

Ben Affleck is undeniably a man of many talents. He is known as an exceptional actor, writer, and director. He is also renowned for his love of gambling, with an impressive affinity for and skills in poker and blackjack.

Affleck has participated in many high-profile poker tournaments, where he showed his prowess at the table and won many events, including the California State Championship back in 2004. In fact, he was one of the celebrities implicated in Molly Bloom’s underground poker ring scandal.

Affleck also has a penchant for blackjack and has often been spotted raking in winnings at many casinos. In fact, he’s said to be quite good, so much so that he got banned by the Hard Rock Casino in Las Vegas for using card-counting strategies back in 2014. However, Ben Affleck’s journey into gambling has not been the smoothest, as he has admitted to periods of struggling with addiction.

Matt Damon

Successful actor, screenwriter, and film producer Matt Damon is another celebrity who is fond of casinos and gambling. Like his longtime close friend, Ben Affleck, this Hollywood A-lister is an avid poker player with a penchant for blackjack. He is often spotted at card tables on the floor of casinos in Las Vegas and is said to have also been involved in Affleck’s fiasco at Hard Rock Casino.

Damon’s interest in poker is said to have started when he was researching for his role in the 1998 movie, “Rounders,” which became one of the greatest poker movies ever. With undeniable skills in the classic game, Damon has participated in different poker tournaments, especially the World Series of Poker (WSOP) events.

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Tobey Maguire

Widely known for his role as Spiderman, Tobey Maguire is another famous and successful actor and film producer with a penchant for casinos and gambling. He is among the few celebrities who thrive in high-stakes poker, having faced many renowned and professional players in different tournaments.

In fact, he has even participated in several World Series of Poker (WSOP) main event championship games over the years, raking in significant winnings.

Along with Affleck, Damon, and other celebrities, Tobey Maguire’s fascination with the poker game led him to participate in Molly Bloom’s famously scandalous high-stakes underground poker ring.

Jennifer Tilly

A-list actress Jennifer Tilly is another accomplished celebrity who enjoys gambling. Her casino game of choice is poker, which she studied diligently over the years, starting from tutelage with her poker-playing father and then-boyfriend.

Unlike many celebrity gambling enthusiasts, Tilly approached poker more seriously and pushed her passion for it to a different level. As a result, she became renowned in the world of poker and soon became a professional player.

Tilly won a WSOP bracelet in 2005 during the Ladies’ No-Limit Texas Hold’em event after beating 600 other competitors and raking in a $158,625 payday. In the same year, she emerged victorious in the World Poker Tour (WPT) Ladies Invitational Tournament.

Tilly has also participated in several other high-profile poker tournaments and earned impressive accolades and recognitions.

Others

Besides the ones mentioned above, many other celebrities are known to enjoy high-stakes gambling. A few other notable mentions include:

  • Leonardo DiCaprio
  • Paris Hilton
  • Michael Jordan
  • Floyd Mayweather Jr.
  • Brad Garrett

Closing Thoughts

The world of gambling has always appealed to regular individuals and celebrities alike. Famous people in films, music, sports, and other industries also engage in casino games, sports betting, and other forms of gambling. However, they usually do so in VIP rooms and with a much bigger bankroll. While some of these A-listers gamble just for fun, others, like those on our list, are known for their outstanding skills and a record of huge wins.

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