High Rollers: Celebrities Who Love to Gamble

For many celebs, the spotlight doesn’t fade when the cameras stop rolling. In fact, some chase an entirely different kind of thrill: the heady adrenaline rush of gambling. Whether it’s poker tournaments or high-stakes casino games, gambling has become a known pastime for many of Hollywood’s rich and famous.

Some stars are discreet about their love for the casino floor, while others make it a central part of their public image. Before we take a closer look at the celebrities who have openly embraced gambling and made it part of their lifestyle, let’s examine why it’s so popular among the rich and famous.

What’s The Appeal For Celebrities?

You might think: “Don’t they have enough money?” Well, yes. But, gambling often becomes a form of entertainment that’s as much about the experience as it is about the outcome.

Celebrities, with their hectic schedules and crazy riders, are naturally drawn to activities that can provide excitement and distraction. On top of this, the sheer luxury and exclusivity of high-end casinos offer them a different level of comfort and privacy that few other places can match. The stakes are high (both literally and figuratively), and the culture of lavish gambling establishments aligns with the type of lifestyle many of these stars lead.

It isn’t just the great and good of Hollywood that enjoy the hobby of gambling; many of us mere mortals are jumping on the bandwagon too – and with good reason. Many online casinos, like the ones listed on cryptocasino.guru, have started accepting cryptocurrency as a payment method, allowing for smooth deposits and withdrawals.

But if you’d rather leave the thrill of a flutter to the A-listers, let’s take a look at those who have embraced the gambling world, bringing their high-stakes lifestyle into the public eye.

Ben Affleck’s Blackjack Expertise

Ben Affleck is not only a Hollywood heavyweight but also a respected name in gambling circles. He’s especially known for his skill at blackjack, where he’s been reported to use card-counting techniques. In 2014, a Las Vegas casino actually asked him to stop playing due to his winning streaks. Affleck later confirmed he had learned to count cards and took pride in playing smart.

In addition to blackjack, Affleck has participated in several poker tournaments and is known to have a competitive streak. His approach to gambling is calculated and focused rather than reckless. Friends and poker players have described him as someone who studies the game and brings real discipline to the table.

Tobey Maguire and the Private Poker World

Tobey Maguire, best remembered for his role as Spider-Man, became a household name not only in film but also in the underground poker world. He was a central figure in the private high-stakes games made famous by Molly’s Game, the memoir-turned-film about the secret poker circuit in Hollywood.

Maguire was known to be highly competitive at the table and reportedly won millions during those years. He played against other celebrities, hedge fund managers, and wealthy business people. While he keeps a low public profile today, his name is still mentioned with respect in poker circles.

Drake’s Casino Livestreams and Big Wins

While he might be keeping a low profile post-Super Bowl, Drake certainly has never been shy about his love for gambling. The rapper and global superstar frequently shares his betting activities with fans through social media and livestreams. He has placed bets worth hundreds of thousands of dollars on roulette and sports events, sometimes in real time with an audience watching.

What makes Drake unique is how he tied gambling into his public brand. He has collaborated with online casino platforms and often references luck, risk, and winning in his music and visuals.

Other Celebrities Who Love to Gamble

While the aforementioned celebs are among the more well-known gamblers in Tinseltown, they are by no means alone. There are many others who love to gamble in high-stakes settings, whether it’s poker tables, sports betting, or casual casino games.

One of these is the famous actor Matt Damon, who starred in the Ocean’s Eleven films, which centered around casinos and high-stakes gambling. Damon is an avid poker player and has been seen at some of the world’s most exclusive poker events. Then there’s actor and comedian Ray Romano, who has played poker for years, competing in several World Series of Poker events.

Additionally, model and actress Shannon Elizabeth is another star who has made a name for herself in the poker world. She regularly plays in poker tournaments and is known for her success at the table. Elizabeth has even appeared in poker-themed TV shows, showing off her skills and passion for the game.

The Influence of Celebrities on Gambling

Celebrity gambling has an undeniable impact on the world of casinos and poker. Their public personas add excitement to the games and contribute to the overall allure of gambling. Their participation also elevates the visibility of poker tournaments, casino events, and other betting activities.

As fans of these celebrities, many people are drawn to try gambling for themselves. Some are even willing to take on the same challenges and risks that their favorite stars take on.

While it is often the excitement and prestige of high-stakes games that attracts these celebrities, their visibility helps make gambling feel so much more glamorous and appealing to their followers.

And who doesn’t want to emulate their favorite stars?

Jesse Miller
Jesse Miller iGaming Writer
Last Updated: April 25, 2025