The gambling world is sure to attract many who seek to test their competitive skills. Like any high-stakes competition, there are the crowned winners and the less fortunate players.

And, sometimes, it’s just sheer luck!

From famous actors who played the movies about gambling we all know and love, to Sports people, we show you the most renowned celebrities that took gambling to the next level!

1. Tobey Maguire

If you are an avid Marvel fan, you surely caught a glimpse of him in the famous Spiderman movies. Yet, aside from the movie scene, Tobey Maguire has his own ‘gambling set’ where he puts together high-stakes Poker events.

In fact, in the 2000s, he used to organize private Poker games with some of the most influential people in the world, from actors like Ben Affleck or Matt Damon to renowned billionaires and even to the Cirque du Soleil director himself, Guy Laliberte.

If the story sounds familiar, you might have seen a visual representation of it, as the ‘Molly’s Game’ movie. Yet, the publicity that came from the movie itself, didn’t save him from getting involved in several lawsuits.

2. Michael Jordan

When we say American basketball, we automatically think of Michael Jordan. Yet, basketball is not the only domain he is passionate about.

Always looking for a challenge, Jordan started gambling as far back as his high school. He usually focuses on table games, such as Craps, and never misses an opportunity to compete against another. As he stated the idea of competition drives him to gamble as much as he does. But this has taken a major toll on his life since he had major losses over the years.

3. Pamela Anderson

The Baywatch star and Canadian American actress Pamela Anderson is no stranger to the gambling world.

Actually, in an interview with Ellen DeGeneres in 2007, she admitted having lost a whopping $250.000 at Poker. Yet, this story didn’t end here since many say that she married Rick Solomon to pay the debt.

4. Matt Damon

Does the movie Rounders ring a bell? Then you might have recognized Matt Damon playing his aces at the Poker table.

And he surely knows his way around gambling games, both in real life and at Hollywood. When it comes to playing Poker, he usually chooses private games, along with another renowned actor, Ben Affleck. He is particularly fond of Texas Hold’em Poker game and casually participated in WSOP events.

5. Jason Alexander

From comedy to gambling, the star of the ‘Seinfeld’ series, Jason Alexander, took Poker play at a professional level.

The talented actor is a regular at the WSOP Main Event and has won $30.000 along with his gambling career. His first encounter with the gambling scene was during college. Alexander always mentions his famous meeting with Poker pro Phil Hellmuth who tried to explain the rules of the games. At first, the actor could not comprehend much of the game itself and that intrigued him as far as to start playing professionally.

6. Brad Pitt

Everyone knows Brad Pitt to be one of the most recognizable and, also, an influential actor of Hollywood. And the impressive collection of awards as well as the numerous outstanding roles he put together speak for themselves.

But did you know that he is also a gambling connoisseur?

He got a passion for gambling while playing his staple roles in Oceans 11. Pitt had to learn all the ins and outs of gambling games, such as Poker or Blackjack, to be able to play his part. And it seems that both the knowledge and the passion have stuck to him since, nowadays, you can spot Pitt in Las Vegas, playing his favorite games.

7. Matthew Perry

We all know Matthew Perry as the sarcastic and hilarious Chandler Bing from ‘Friends’. He always had the best comebacks and the audience burst into laughter at his ironic statements.

Aside from coming up with iconic jokes, Matthew Perry also likes to pit his wits against other gamblers. He has an affinity with Poker and is quite a regular player at the Bellagio casino in Las Vegas. And he also pitches in charity tournaments when he has the chance.

8. Sean Connery

You must have heard the name ‘James Bond’ at least once in your lifetime. Yet not many people know that Sean Connery (the first Agent 007) was an actual gambler in real life. And quite a successful one, we might say!

In 1963, he won an astounding $27.000 playing Roulette at Casino de la Vallee, in Italy. His luck was clearly on his side since he bet on the number 17 and won 3 times in a row.

9. Ben Affleck

The famous actor Ben Affleck is no stranger to gambling. On the contrary, we could say that it has become a compulsive passion to him.

He started as young as 21 and qualified for the WPT, in 2004. However, his passion quickly turned into an addiction which later made him seek professional help. He even got banned for life at Hard Rock Casino for allegedly counting cards at high-staked Blackjack games.

10. George Clooney

Another iconic actor that played in the ‘Ocean’s’ series is George Clooney. We know him to be a permanent appearance in action movies, but, aside from his career as an actor, Clooney is also interested in gambling.

He gradually became so passionate about gambling that he went as far as to invest $3 billion in the Las Ramblas Resort which included a high-end casino, back in 2005.


More and more celebrities try to get into the world of gambling, filled with glitz and glamour but also with the high possibility of major losses. We have seen how gambling transformed their life for the better, or for worse.

No matter what, it is always important to remember that gambling comes with a great deal of responsibility!