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7 Stars Who Love to Gamble

Movie stars, musicians, and athletes love to gamble just as much as the rest of us. They often have more money to throw around, but they also know how to have a good time. For some, gambling is a casual pastime. They might enjoy a friendly game of poker with friends or betting on the occasional horse race or football game. For others, gambling is a serious addiction that has caused them financial ruin.

Here are seven famous people who love to gamble.


Drake is one of the biggest names in music right now. The rapper has been known to drop serious cash at the casino. He has publically won and lost hundreds of thousands of dollars at a time, and most recently, he’s been in the spotlight for betting over a million dollars on UFC fights.

Drake loves to post his wins and losses publicly and is always sure to let the camera zoom in on the app he uses, ‘Stake,’ which he just so happens to be a partner in.

Talk about loving gambling! Drake loves it so much that he partnered with a popular sportsbook!

Tobey Maguire

Many people know Tobey Maguire from his role as Spiderman, but he’s also an avid gambler. He allegedly won over $10 million dollars playing high-stakes poker games with celebrities and Wall Street executives. That said, he’s rumored to have lost 300k in one sitting. He’s also been known to place big bets on sports games and was sued for his part in a massive, multi-million dollar illegal gambling syndicate.

Shannon Elizabeth

Shannon Elizabeth is a former model and actress who has starred in movies like American Pie and Scary Movie. These days, she’s better known for her skills at the poker table. Shannon Elizabeth is a legitimate threat at the poker tables. She’s won several major tournaments and has even written a book about poker.

Ray Romano

Ray Romano is best known for his role in the long-running sitcom Everybody Loves Raymond. But did you know that he’s also a fan of gambling? He’s been known to play poker and blackjack and admitted that he had a serious problem, losing thousands of dollars at a time betting on sports through backroom bookies and in Atlantic City. Thankfully, he was able to recover and address his gambling problem. Even his wife called him a maniac when he sits to play blackjack, speaking specifically of watching him play at the Riviera Hotel.

Matt Damon

Matt Damon is one of Hollywood’s biggest names and he’s also a big fan of gambling. He’s been known to play high-stakes poker games with Tobey Maguire, Shannon Elizabeth, and Ben Affleck. He even produced a movie about gambling called Rounders. In the movie, he plays a reformed gambler who has to return to the tables to get his father out of trouble. There were rumors that the movie was based on happenings in Norm McDonald’s life. The rumors were proven false; however, Norm McDonald lived through a similar experience of playing backroom poker games with shady folks.

Ben Affleck

Ben Affleck is another Hollywood A-lister who loves to gamble. He’s been known to play high-stakes poker games with Matt Damon and Shannon Elizabeth. He also produced a movie about gambling called Runner Runner. In the movie, he plays a businessman who cheats a player out of his life savings in an online poker game and then travels to Costa Rica to confront him. Affleck reportedly when into a gambling treatment program in 2001. So, not only does Ben Affleck love to gamble but similar to Ray Romano, he had a serious problem with it.

Adam Sandler

Adam Sandler is a famous comedian and actor who has starred in movies like The Waterboy, Billy Madison, and Uncut Gems, a story that takes a unique look at gambling addiction. But Instead of getting involved with shady NY bookies and loansharks, the protagonist should have just stuck to trustworthy New York sports betting apps.

Adam Sandler also has funny gambling stories, one in particular when he lived in the same building as Norm McDonald and went up to his apartment to hang out. He asks Norm for a soda and opens the fridge to find $25,000.00 in Atlantic City poker chips on the refrigerator shelf. Adam Sandler is blown away and asks why there is over 20K worth of chips in the fridge and why he did;t cash in the chips, to which Norm replies, “I won big on Friday! But I brought it home to ask Bernie Brillstein—a producer—how not to pay taxes on it.” A couple of days later, Adam asks Norm if he cashed in those chips, and Norm replies, “No! I lost it all!”






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