Top 7 Celebrities in Gambling & Frequent Casino Visitors

5 min readMar 31, 2021


Gambling is an ancient form of entertainment not just exclusive for the masses, as there are also many celebrities in gambling.

It’s no secret that most celebrities like to live the Rockstar life and spend their money on their hobbies, and for many of them, that includes gambling. As much as they love to play different characters in front of the camera, many celebrities also enjoy playing poker, roulette, or other casino games.

These seven celebrities in gambling are famous for their fair share of wins, losses, and massive spending habits when playing at casinos.

1. Michael Jordan

Michael Jordan is well-known as one of, if not the greatest, basketball players in history. He bagged several titles playing with the Bulls and earned himself Finals MVP titles for them. His history in the game doesn’t only show his skills but also his competitiveness. Jordan’s competitive streak isn’t only in the court, as he’s an avid casino player too.

Michael Jordan’s gambling habits are well documented, in and out of the casino. His gambling antics supposedly involved betting with his teammates for $100k if his bags first arrive at the baggage claim, which he won. There was also a bet on a single hole of gold which, unfortunately, lost him a million dollars.

Jordan is one of the biggest celebrities in gambling, a frequent VIP room visitor in several casinos, where the gambling action is always massive.

2. Charlie Sheen

The actor got famous for his role in ‘Anger Management,’ ‘Young Guns,’ and ‘Spin City.’ However, acting isn’t only what he’s popular for, because he’s also among top celebs well-known for their casino habits.

Denise Richards, the actor’s ex-wife, once highlighted Sheen as one of the celebrities in gambling. She even said that the actor could spend as much as thousands of dollars every week on sports betting alone.

3. Floyd Mayweather

Floyd Mayweather is famous for many things, and being one of the richest athletes in the US is only one of them. His years of being a top name in the boxing world earned him over $500 million. With that kind of wealth, it wouldn’t be surprising that the athlete is among the biggest celebrities in gambling. After all, he can afford to make large bets and not go broke even if he loses.

Mayweather isn’t shy about telling the public about his gambling antics either. He has shared details about bets he’d made, including bets worth six figures to a million dollars on a single bet.

4. Ben Affleck

Many high-profile celebrities have a gambling history, and one of the more celebrities in gambling include Ben Affleck. He is not only a Hollywood A-lister but a famous casino player as well. Ben Affleck has a long history of playing in casinos, and he is also among them who got success and a lot of money from it.

Besides his frequent casino visits, Ben Affleck is also well-known for being generous with the tips he gives casino employees. He’s rumored to favor playing poker, where he lost thousands of dollars, prompting him to go to rehab in 2001. Still, it wasn’t long before he went back to the tables and eventually won California State Poker Champion in 2014.

Among his immense history in gambling includes a long-time ban on blackjack at Hard Rock Casino. But unlike bans imposed on some celebrities due to bad behaviors in the casino, Affleck’s was primarily because of the uncanny memory that allows him to count cards without help from a team.

5. 50 Cent

50 Cent is famous for several things, and a regular casino player is only one of them. He’s a famous and successful modern-day rapper, selling millions of albums, which skyrocketed his net worth to several millions of dollars.

However, all those millions didn’t go into investing in stocks and securities. Most of the 50 Cent’s wealth went into his lavish gambling habit, including an alleged $2 million bet in a Floyd Mayweather fight. 50 Cent is an avid gambler and a sports-betting enthusiast, famous for betting hundreds of thousands of dollars on football events.

6. Tiger Woods

Being a famous golfer and one of the wealthiest athletes makes Tiger Woods a household name. However, he is not only popular in the world of sports. He is famous in the gambling space as well. Tiger Woods has demonstrated his strong competitive streak, whether on the golf course or a casino.

With a net worth of around a billion dollars, Tiger Woods has a lot of disposable income, and it’s not surprising that he disposes of his wealth by playing blackjack. Then again, the athlete rarely loses, so you can’t call it disposing of his money.

7. Tobey Maguire

Another celebrity with a well-documented gambling habit is Tobey Maguire. After becoming the first actor to play the role of Spider-Man on the big screen, he became a household name. While that part of his career is long gone, Toby Maguire also became one of the famed celebrities in gambling, especially among Hollywood A-listers.

If there are celebrity poker tournaments, Toby Maguire is most likely going to be there. The movie star is a regular in Las Vegas poker rooms and even participates in the World Series of Poker.

You can easily see his dedication to playing poker or gambling in general after the news of the investigation of an underground poker ring, in which he was deeply involved. It was a poker ring for the start that involved dozens of power players in Hollywood.

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