Celebrity Gamblers: Who Bets Big?

While not everyone spends their life in a casino, many individuals try gambling at least once, including celebrities. When you think about it, it makes sense, because what else are you going to do with all the money one makes when acting in A-list movies?

Of course, you probably assumed celebrities gamble, but do you know which ones bet the most? We’ve investigated for you, so keep reading to learn which celebrity gamblers bet the most.

1. Ben Affleck

Though he hasn’t placed the largest bets on our list, the former husband of Jennifer Lopez is well known in a variety of casinos in both California and Las Vegas. Usually spotted at the blackjack table, it’s difficult to track his winnings, but we do know he is banned from several casinos, including the Hard Rock in Las Vegas, because of his reported abilities in card counting.

2. Toby Maguire

Another frequent flyer on the list of celebrities who gamble is Toby Maguire, who is most well-known as the actor who played Spiderman. Toby Maguire’s game of choice is poker, and he’s actually a decent player, first rising to prominence during a series of illegal and secret underground games (Molly’s Game, anyone?). His largest win is supposedly somewhere around $36 million, though we suspect he’s lost a lot of money off the books, too. He’s backed off in recent years (since the underground ring went under), but before that happened, he was a well-known winner in his circles.

3. Pamela Anderson

The first female on our list, Pamela Anderson, is a known high roller, especially around the poker table. These tactics of flinging millions she doesn’t have on the table have reportedly caused trouble for the former Baywatch actress, who apparently got married to a man to settle her gambling debt. Of course, the marriage was short-lived, but she did emerge from it debt-free.

Pamela Anderson mostly gambles online now, though in her heyday, it was common to find her at a poker table in casinos in Las Vegas.

4. Matt Damon

Not all celebrities who gamble are talented at it, most notably actor Matt Damon. While he does play poker and has participated in the WSOP at one point, he unfortunately has some of the lowest winnings on this list, barely breaking $100,000.

Still, Matt Damon was trained on how to play poker by Daniel Negreanu, one of the most famous professional poker players in the world, to prepare for a film role in the movie Rounders. Therefore, we would expect more winnings from him, though many other players have praised his tableside manner.

5. George Clooney

This will probably shock you, but the silver fox himself can often be spotted in the VIP rooms in Las Vegas. In fact, he was a major investor in the failed Las Ramblas resort. Like fellow actors Matt Damon and Toby Maguire, George Clooney plays poker. Not only that, but he has reportedly won over $1 million USD over the years.

Las Vegas isn’t the only destination where George Clooney can be spotted; in fact, he is often also seen gaming in Monte Carlo.

6. Paris Hilton

Another female gamer, Paris Hilton, obviously has the money to spare. Like George Clooney, she is a frequent guest in both Las Vegas and Monte Carlo, but you likely won’t ever find her at your table, as she loves the VIP rooms. Like George, she has won a lot of money over the years, and regularly dabbles in both poker and blackjack. Unfortunately, she is also banned from several resorts, most notably the Wynn.

7. Brad Pitt

Reportedly, ever since filming Ocean’s Eleven, Brad Pitt can’t get enough of the tables. Like most of the other celebrities on this list, he mostly plays blackjack and poker, though we have very little information about where and how much he’s won over the years. That being said, he does regularly frequent both Las Vegas and Monte Carlo, but we aren’t sure which casinos or how frequently.

8. Jennifer Tilly

Jennifer Tilly is proof that you can have it all—an acting career and a WSOP bracelet. Although her last major win was the 2005 WSOP, Jennifer still pops up on the poker circuit frequently. She still plays tournaments around the globe, though she’s been spotted less and less following the COVID pandemic.

9. Michael Jordan

There is no doubt about it, Michael Jordan is one of the best athletes of our time, and unfortunately for himself, huge into gambling. Not that gambling is bad, but like some of the other celebrities on this list his known gaming habits have cost him aspects of his career—most notably certain brand deals who have backed out of working with him when the rumors were confirmed.

10. Charles Barkley

Not all celebrity gaming stories are happy ones, and Charles Barkley is one of the sad ones. Charles loves both sports betting and casino games, and has, unfortunately, lost upwards of $25 million USD over the years. Although he says he has no regrets, we suspect that he must regret some of his larger losses at least a little.

11. Floyd Mayweather

Floyd Mayweather, the famed basketball player turned boxer, has one vice—and that vice is sports betting. Of course, he has the money to spend, but many speculate with his lavish lifestyle as to whether or not he will be able to keep it up. You might shake your head and laugh, but know that Mayweather frequently places millions of dollars on single bets—and not even the big ones. Though he brags about winning, to be honest, we aren’t so sure.

12. Tiger Woods

Like most celebrities on this list, the famed golfer Tiger Woods is often spotted in Las Vegas, superficially at blackjack tables where he has been known to bet $25,000 per hand. Over the years, there have been a lot of rumors about Tiger Woods(most notably his affairs), but unlike other celebrities on this list, we don’t think his reputation has suffered, as he still reportedly nets about $2 billion per year from his investments and endorsements.