Gambling is a staple among many celebrities.
Whether they’re famous for acting, music or professional sports, time at the casino or in poker rooms comes with the territory. And that makes sense. Celebrities often have a ton of disposable income, and gambling can be a way to pass the time, bond with peers, challenge mental faculties or just incite a good time.
Pro athletes, for instance, are known to play high-stakes card and dice games on plane rides to contests away from home. Musicians will sometimes hang out in the high-rollers sections of casinos that house or are near a venue they are playing. And actors, in many cases, study gambling for roles; just as some newbies will search for insight on how to bet in Canada or the best casino games for beginners in the United States, they will try to read up and learn the ins and outs of cards, roulette, craps or whatever the particular part demands they be an expert in.
But regardless of whether celebrities get into gambling for work, play and leisure or just flat-out because, some of them get really into it. Like, really, really into it. We’re talking about weekly private poker games with huge buy-ins or legendary trips to the casino in which they drop six figures or more at one table or even on one bet.
For most of us, these stories and habits are entirely unrelatable. But they’re still really fun to discuss. So let’s take a look at some A-list names, from all walks of fame, who are known to appreciate a good bet.
Raise your hand if you’re surprised.
What? No hands in the air.
Yeah, that makes sense.
The movie Rounders, which was a tale of two gamblers, represented one of Matt Damon’s first starring roles in Hollywood. He needed to learn Texas Hold ‘Em for his lead part, alongside Edward Norton. And though Damon always needed to know the game inside and out for authenticity, the research for his role ended up sticking.
Everything you see on-screen from him is genuine. He learned how to handle cards and chips with precision and immersed himself in the lingo. Playing in tournaments and visiting casinos helped him pick up on it all.
Still, Rounders was released in 1998. Fast forward more than two decades later, and he continues to be known for his interest in poker, both in charity tournaments and at casinos. He’s even famous for showing up at some private weekly games hosted by fellow celebs.
Ben Affleck also held a prominent role in Rounders, but his interest in gambling predates his ascent through Hollywood. Believe it or not, he was once thrown out of a casino—and subsequently banned from it—for counting cards at a Blackjack table.
Of course, it was Rounders that increased his interest in poker specifically. Long after the movie wrapped up filming, when he was no longer obligated to envelop himself in the culture, Affleck is said to have spent nearly six figures on a coach who helped train him in every aspect of every poker game imaginable.
Like Damon, he, too, is known for attending the private poker games and tournaments hosted by his celebrity peers. And it seems his investment in a poker coach paneed out.
At one point, he won nearly $1.2 million combined in two different tournaments. It would appear those lessons paid for themselves—and then some.
Perhaps no one in modern Hollywood is known more for their gambling affinity than Tobey Maguire, who continues to be most recognized for his work within the Spider-Man franchise.
While Maguire will play in a lot of the same higher-stakes games and tournaments as Affleck, he’s also more inclined to frequent casinos to get his fix. Not only that, but he used to host his own invite-only poker game—which included guests like Affleck, Damon and Leonardo DiCaprio—at The Viper Room in California. The game is no longer a regular occurrence (it stopped after briefly being moved to an undisclosed location in New York), but its existence speaks to Maguire’s overall commitment to the craft.
Contrary to Affleck and Damon, who both prefer Texas Hold ‘EM, Maguire is an Omaha enthusiast. And to answer your question: Yes, he has many six-figure victories under his belt.
Jennifer Tilly isn’t the biggest household name—though, you would recognize her if you saw her—but we have to include her in this exercise. How could we not?
Sure, the actress with credits in well-known movies like Chucky and Monsters, Inc. started playing poker as a side hobby. But she’s since turned into an actual professional poker player.
And when we say actual, we mean actual.
Tilly isn’t just some red-carpet face who decided to buy into the World Series of Poker. She actually won a World Series of Poker bracelet and a nearly $160,000 prize pool at the Ladies’ No Limit Texas Hold ‘Em tournament in Las Vegas.
No other celeb on this list has that type of official victory to their name.
Brad Pitt did not catch the gambling bug until later in his illustrious career. And we’re guessing you can pinpoint when: immediately after he played his part in Ocean’s Eleven.
Whereas the previous four celebs fell in love with poker or blackjack, Pitt enjoys playing slots. He could often be found in-between takes and scenes during Ocean’s Eleven filming trying to play and learn as many different games as possible. We’re guessing his interest peaked as the character tasked with testing out all the different rigged slot machines in the movie.
Anyway, Pitt’s interest didn’t dissipate following Ocean’s Eleven. For starters, he appeared in the franchise’s two sequels, the latter of which, Ocean’s Thirteen, took place in many different casinos. More than that, though, Pitt is known to have retained his affinity for slot machines when visiting Sin City for non-business reasons.
On top of that, because he rolls within a social circle directly adjacent to Damon and Affleck, he’s more recently become a poker enthusiast, as well.