High Rollers Unveiled – Celebrity Gamblers!

min read
four well dressed people, two men and two women, sitting at a roulette table placing bets and cheering each other on in a casino
BetMGM Jul 06, 2023, 11:00 PM

Gambling has always been a popular pastime for the rich and famous. Whether it’s sports betting, casino table games or poker, celebrities just love to splash their cash. 

Let’s take a look at some of the world’s most famous gamblers. All of these high-profile celebs are known to enjoy a high-stakes flutter or two.

Tobey Maguire

It’s no secret that the “Spiderman” star is a huge fan of poker. Although the actor frequently shows up at celebrity poker games, Maguire is more than just a casual player. At one time, he was known to have received regular tuition from Daniel Negreanu, one of the most successful poker pros in the world.

Although he hasn’t participated in any high-profile tournaments for a number of years, Maguire does have three World Series of Poker cashes on his resumé. In 2007, for instance, he made a deep run in the Main Event, finishing 292nd for a $39,445 payday. But his best-ever score came in 2004 at the Phil Hellmuth Invitational, where he won for $95,480.

Michael Jordan

Not only is Michael Jordan arguably the best player ever to have graced the basketball court, but he’s also earned a reputation as one of the biggest celebrity gamblers around. Although not much of a casino game player, his competitive nature would come out in spades on the golf course. His Airness was known to frequently make high-stakes bets while playing with the likes of Charles Barkley and Tiger Woods, for instance.

It’s thought that Jordan first got into gambling while studying at North Carolina State University. And at certain points in his life, he has freely admitted to it becoming a problem. However, MJ is worth more than a billion dollars these days, so he can certainly afford his hobby. 

Leonardo Di Caprio

One of the biggest names on our list of high-profile celebrities who enjoy gambling, Leonardo Di Caprio needs no introduction. Widely known for his many incredibly successful Hollywood roles, his penchant for gambling is perhaps a little less public. However, Di Caprio is most certainly a casino lover.

It’s thought that his interest in gambling was first triggered as a teenager, watching his father participate in games. And although it’s impossible to verify, reports suggest that the actor has won over $30 million from various poker tournaments and casino table games. But for a man of Di Caprio’s wealth, gambling is clearly not about the money. Instead, the pleasure lies with getting lucky at the felt.

Matt Damon

Star of countless Hollywood movies, Matt Damon famously appeared in a cult classic about poker called “Rounders.” Just one example of how pop culture is shaping the gambling scene, quotes from the script could be heard at the poker table for many years after its 1998 release.

Not unlike his character in the film, Damon also enjoys playing poker, often with his friend and fellow actor Ben Affleck. Although he has never enjoyed success in a notable poker tournament, the star of “Good Will Hunting” is said to be a big fan of gambling behind closed doors.

Ben Affleck

As we mentioned, Affleck and Matt Damon are as thick as thieves in real life, often hanging out while not busy making hit movies. And poker is a big hobby for both of them. However, Affleck is undoubtedly the more successful of the two, having earned over $360,000 from playing live poker tournaments. 

The bulk of his publicized career earnings came in the 2004 California State Poker Championship, where he won the $10,000 Main Event. That score in Los Angeles saw Affleck pocket an impressive $356,400. But who knows how much the high-rolling actor has won and lost while playing online casino games?

Floyd Mayweather Jr.

One of the most legendary boxers of all time, Mayweather’s nickname “Money” exists for a good reason. Flash with the cash, he’s not shy about showing off his multi-million dollar career earnings. But it’s not just fast cars, clothes and bling you’ll see on his social media accounts. Mayweather is known to brag about his high-stakes sports betting antics, too, posting screenshots of his big wins.

As one of the wealthiest and most successful sportsmen in history, Mayweather can certainly afford to lose a bet now and then. But it’s been reported that he once lost almost $50 million dollars in a single year!

Paris Hilton

Although more famous for her work in modeling, television and dubious sex tapes, Paris Hilton is also known to frequent the casino. In her younger days as a socialite, she was often found at the felt, gambling with the likes of Leonardo DiCaprio. 

Hilton famously celebrated her 31st birthday in Las Vegas, where she posted on Twitter about winning $30,000 playing blackjack. A little older and wiser now, she’s less active on the social circuit these days. Although we can’t quite imagine her sitting at home, quietly enjoying high-stakes online blackjack live dealer games.

Ray Romano

“Everybody Loves Raymond” remains a hugely popular television show today. It stars Ray Romano as an everyman sports journalist and family man living in suburban America. But in 2009, Romano created a new series called “Men of a Certain Age,” which tracks the story of gambling addict Joe Tranelli.

It’s well-known that Romano enjoys playing poker and has been seen playing World Series events in Las Vegas. But it was only in 2011 that the actor confessed that the Tranelli character was actually based on his own life. Romano had even sought the help of Gambler’s Anonymous. The real-life story seems to have a happy ending, though, as Romano appears to have overcome his issues. These days, he only gambles for fun at low stakes.

Gambling Isn’t Just for Celebrities

Few hobbies can offer the same thrill as gambling. And you, too, can get in on the action like your favorite celebrities. But there’s no need to wager millions to feel that buzz. Simply register at BetMGM and play casino games online at a wide variety of limits.

Enjoy player-friendly, low-stakes table games, including roulette, blackjack and craps. Not to mention hundreds of the latest video slots and daily poker tournaments. 

Actress Vanessa Hudgens flipping casino chips next to the text "The King of Casinos"
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Our BetMGM editors and authors are casino experts with a wealth of knowledge of the online casino industry at all levels. Their coverage includes company news, game reviews, how-to instructional articles, strategy guides, and editorials showcasing BetMGM’s superior product and game library.

Our BetMGM editors and authors are casino experts with a wealth of knowledge of the online casino industry at all levels. Their coverage includes company news, game reviews, how-to instructional articles, strategy guides, and editorials showcasing BetMGM’s superior product and game library.