It’s no secret that being wealthy and famous is a stressful lifestyle, but celebrities can relieve the stress of their demanding jobs by letting their hair down and throwing lavish parties. The general public’s fascination with the activities that occur when A-list celebrities are isolated from the rest of the world is as strong as it has ever been.

Other than boozy parties at the Playboy Mansion and Oscar after-parties at the homes of Hollywood’s most powerful people, there’s a lot going on in Hollywood. In fact, many celebrities prefer to unwind by gambling away their weekends at casinos or hosting their own high-stakes casino games in their homes.

Here is a list of some of the world’s most famous people who enjoy getting their party on by playing live casino games.

George Clooney is an actor.

When you think of famous people who enjoy gambling in casinos, George Clooney is likely to be the first name that comes to mind. After all, his most famous film role was as Danny Ocean in the Ocean’s Trilogy, despite the fact that he prefers to gamble in casinos rather than plotting to steal money from them in real life.

The actor has spent a significant portion of his life pursuing his interest in casino games, even before he became a household name in the 1990s. However, this does not imply that he is particularly skilled at them; according to urban legend, his Ocean’s co-star Matt Damon once had to save him from financial ruin after he lost 25 consecutive hands of blackjack.

George Clooney, on the other hand, had the last laugh when he finally paid back his friend who had won an Academy Award by handing him a check marked “for lap dances.” Clooney was the last man standing. We’ll never know what the bank teller thought when Matt Damon walked in with that check.

Both George Clooney and Matt Damon are avid gamblers, and at one point, the two actors discussed the possibility of opening a casino on the Las Vegas strip in collaboration. That didn’t work out, but it’s clear that their enthusiasm for acting inspired the rest of the cast of the 2001 blockbuster film.

Brad Pitt began playing slot machines and card games during breaks while filming that movie in Las Vegas, and it appears that he is still a fan of gambling to this day. It’s clear that George Clooney was the one who set the trend for his fellow actors.

Affleck, Ben

When Matt Damon and his well-known best friend want to let their hair down, they like to hang out at ritzy Las Vegas resorts. Ben Affleck, on the other hand, is in a completely different league than Matt Damon, who only plays Texas Hold ‘Em for fun.

He is famous for being kicked out of the Hard Rock Cafe in Las Vegas for the rest of his life because he has won so many significant cash prizes there. He once had a session in which he won $140,000 in a single sitting, but instead of cashing out his winnings, he distributed them among the casino’s employees.

The next time he came back, he won $800,000 by participating in three different hands at the same time. In a 2016 interview, he admitted that his obsession with blackjack had gotten to the point where he could count cards without thinking, which we do not recommend.

The actor has won multiple championships at high-stakes poker in California, and he has even put his knowledge to good use. In the year 2020, he hosted an online poker tournament that raised over $1.7 million for food banks. The tournament featured celebrities such as Adam Sandler, Bryan Cranston, Tom Brady, and Jon Hamm.

Tobey Maguire is an actor.

Despite losing to Ben Affleck in the California poker championships in 2004, the actor who formerly played Spider-Man has gone on to become one of the best A-list players. If you’ve seen the film Molly’s Game, you might be surprised to learn that Michael Cera’s character, a famous poker player, was inspired by Tobey Maguire.

However, the actor’s poker tournaments in the early 2000s had even higher stakes than the film made them appear to have. Between 2005 and 2009, a number of well-known actors, including Leonardo DiCaprio and the aforementioned Ben Affleck and Matt Damon, were regulars at the Viper Room in Los Angeles on Tuesday nights.

Despite the fact that they were joined by other wealthy and influential Hollywood players, one of the players commented that the games were so intense that winning $20,000 felt like losing. However, not every player was a good sport. Leonardo DiCaprio, the group’s richest actor, was initially hesitant to put down the $5,000 buy-in required to participate in the game.

To put that in context, his net worth was estimated to be $80 million at the time. It should come as no surprise that Maguire’s poker parties, which are among the most infamous in Hollywood history, served as the inspiration for a successful film.

Tilly, Jennifer

Famous people enjoy the thrill of gambling so much that they have quit their day jobs to pursue a career in the industry. Jennifer Tilly was nominated for an Academy Award in 1994, and only a few years later, she starred in critically acclaimed films like Liar Liar and Stuart Little.

However, in the end, she realized that her true passion was at the poker table. She triumphed in a ladies’ Texas Hold’em event at the World Series of Poker in 2005, earning a bracelet in the process.

She stated the same year that she preferred a career in professional poker to acting, and by 2017, she had earned nearly one million dollars in total winnings from poker.

Casino games may begin as a casual thrill for some celebrities, but they can grow into an interest that rivals or even surpasses making movies over time. A-listers enjoy casino excitement in whatever form it takes, whether it’s letting loose in Las Vegas or hosting their own casino tournaments, and this is unlikely to change in the near future.