Celebrities Who Love to Gamble in Their Free Time

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Nearly everyone dreams of becoming a Hollywood celebrity in the future. Actors, musicians, and other people in showbiz seemingly lead a perfect life. They look cool, they have the money for an expensive lifestyle, and are seemingly successful in any field. However, they’re just people like the rest of us. Many of them enjoy simple things like gambling, and can often be seen on tables at Las Vegas casinos.

For many, it’s a vice. However, the lure of casino online games is too strong to ignore, and even celebrities are not safe from it. If done correctly—like many of the celebs on this list do—gambling can be a very fun pastime. Here are the biggest Hollywood celebrities you may meet on tables in Las Vegas.

Ben Affleck

We’ll start off with the Hollywood star and ex-Batman actor Ben Affleck who can easily be the face of any Vegas casino. Ben Affleck’s love for gambling has been well documented. What many don’t know is that he’s a very successful gambler too. The Hard Rock casino banned Affleck from ever setting foot inside again, after he won close to a mil in two visits. Affleck’s ‘poison’ are card games, particularly blackjack and poker, and he won the California Stake Poker Championship in 2004.

His love for gambling also landed him a role in the 2013 thriller Runner Runner. Affleck plays a poor college student who goes bust playing rigged online casino poker games, which turns into a nightmare of its own. The movie didn’t pass that great at the box office, but Affleck’s reputation didn’t suffer at all.

Tobey Maguire

Yep, quiet Tobey Maguire loves playing poker, and he’s quite a good player too. According to sources, he’s no stranger to high roller poker tables, and has won quite the sums over the years. In 2011, he apparently won over $100,000 in poker tournaments. He also won the Hollywood Park Casino tournament, so he may very well be just as successful in Affleck in this term.

George Clooney

George Clooney is a famous high roller, although he likes to enjoy his favorite card games far away from prying eyes. Many have mentioned that he’s quite the big tipper in Vegas, and that he loves frequenting poker tables. In 2005, he even started proceedings into acquiring a Las Vegas casino, but it never went through. Nevertheless, his gambling chops have surely been a major factor for Clooney acquiring roles in hits such as Ocean’s Eleven and its sequels, which are famously set in Vegas.

Matt Damon

Affleck’s and Clooney’s best bud Matt Damon is a well-known gambler in Las Vegas. He has appeared in more than one gambling movies, including Rounders and the Ocean’s sequels. He once said he developed a love for it during his law student days. To prepare for his role in Rounders, Damon was coached by poker legend Johnny Chan.

It didn’t stop there. Damon brought his A game to many poker high roller tournaments, and has raked in millions in prizes.

Charles Barkley

Charles Barkley’s love for gambling has been documented over and over. The former NBA star himself admitted to going bankrupt because of it. Luckily, he’s found a new job in media that allowed him to pay off his debts.

He has openly talked about his gambling addiction and shared incredible details of his days in Las Vegas. Barkley reportedly lost over $1 million a day 20 or more times. He was worth $60 million, but managed to destroy his bankroll. He confirms it’s a bad habit, but never vowed to quit – he just promised he’ll be more careful with his money.

Neymar

Brazilian football star Neymar is an avid poker player. He can be seen at the most lavish casinos around the world, but he also loves playing online. He’s become the poster boy for famous gambling site PokerStars, and once a week, he plays poker online against regular players.

Earlier in 2023, Neymar made fun of him losing nearly $1 million in just an hour at a poker tournament. He has money to spent, but if he doesn’t want to end up like Barkley, he’d better watch out on those bets.

Michael Jordan

Many have called Michael Jordan the GOAT, and he’s definitely one of the best basketball players in the history of the sport. He’s also a very famous big roller in Las Vegas, making—and losing—a lot of money on blackjack tables.

Jordan has never shied away from it. He can be seen drinking and playing blackjack in Vegas just like regular people. The difference between him and Barkley is that he has more money to burn, and he’s a bit more successful too. Jordan is a billionaire who just made more money by selling his stake in the Charlotte Hornets.

Jordan has won millions and lost millions too. He doesn’t consider it a problem at all, and it won’t be long before we see picks of him playing his favorite games on the web.

Ray Romano

The Everybody Loves Raymond star has participated in the World Series of Poker tournaments several times so far. Many of his co-stars have said he’s more than a capable poker player. He may not have won any WSOP bracelets, but he’s said to have won smaller tournaments on a state level.

Floyd Mayweather Jr.

Boxing icon Floyd Mayweather Jr. loves betting in Vegas. He’s more of a sports betting guy than a casino player, although he can be seen playing card games in Vegas as well. The flashy fighter is worth over $1 billion and not afraid to post his incredible bets and earnings online. For example, in 2012, he put $1.1 million on a college football match between Oregon and Arizona State. He won that bet, but there have been many times when he’s lost sums similar to that one.

One thing’s for sure – he’ll never back down from anything (or anyone). That’s why they call him Money.