You’ll often hear that gambling is a poor man’s game. That’s not true. Gambling is for everyone. No matter how rich or famous you are gambling will have the same appeal to you as it would for any of us Average Joe’s. It’s fun and exciting, it makes your blood boil and your heart beat faster.

So, trust us when we tell you that not even the biggest of celebrities can escape from gambling activities. The only difference is that those who are rich and famous have more money to squander. 

This is where our focus for today will be. You’re certainly interested to learn about your favorite celeb and his mishap in the casino. It has happened on numerous occasions. Maybe we will not cover your favorite movie star, athlete, or singer, but these names will certainly ring a bell.

So, without further ado, let’s dig deep into the hole from which not even celebrities can dig themselves up – the casino loss. Keep reading and find out about some of the most epic gambling losses ever directed by celebrities we love and know from different perspectives. 


When it comes to lists like these Drake is always the first name that pops up. After all, we are talking about one of the biggest names in the music industry today. The Canadian rapper is well-known as a sports fan, being a frequent visitor at Toronto Raptors games.

He’s also a big fan of sports betting and online gambling. Considering how much he’s worth, it’s not hard to tell that he managed to lose a few bucks while at it.

The famous artist is well known as a man who puts a curse on the team whose shirts he sports. It is well documented that he managed to curse the likes of Juventus, Arsenal, and Paris Saint Germain.

One of his most recent and biggest losses came last year during the World Cup final. Drake put $1 million on France winning it all in regular time. He lost, and the French team lost on penalties. The curse is real

Ben Affleck

Because he’s Batman! No, that’s not the reason for Ben’s constant gambling losses. Joking aside, the reason is simple. He loves a good visit to a casino, and he has money to waste. Affleck is a big name in the movie industry and is one of the most decorated Hollywood actors and directors. He’s also famed for his casino outings.

We can’t say that we saw him playing at, but it’s well-documented that he managed to win $356,400 at a state poker championship in California almost two decades ago. While a serial winner you should also know that he wasted $400,000 in a secret Hollywood poker game where he was bettered by the director of the Universal Studios, Ron Meyer.

His gambling woes can be put aside considering that he’s back at it with Jennifer Lopez which is a massive win on its own. 

Michael Jordan

The GOAT of basketball has had some rough gambling moments during his career and in the years that followed. He’s one of the rare athletes who managed to build his brand even after his career ended, becoming a billionaire in the process. Good for Jordan. But, MJ always loved a good game of blackjack.

As a highly competitive man he has not taken losses lightly, but gambling doesn’t pardon anyone no matter how good you are. Back in his heyday, he paid %57,000 in casino losses. But that’s not a large sum, isn’t it? It’s not.

The large sum Jordan managed to lose is $1 million, which is a rumored sum he lost during a single game of golf. What can you say? The man loves to gamble on himself. It’s a shame he’s only so good at basketball and not in the gambling domain. 

Pamela Anderson

If you grew up in the late 90s and early 2000s you know who’s the biggest Hollywood star. Pamela Anderson was an icon of television and no one can say otherwise. In addition to being one of the most good-looking actresses in the world, she was prone to gambling. This is a well-known fact and not even Pamela is running away from it.

The Baywatch star was a frequent visitor in Las Vegas. During one long night of poker, she managed to lose $250,000. To make things even more interesting there’s a tale that states that Ms.

Anderson managed to pay off her debt through means that haven’t included paying any money, but we won’t go into details on that occasion. We’ll leave it to your imagination or a quick Google search to find out what we’re insinuating. 

Charlie Sheen

Charlie Sheen

The man of the people. Sheen is the famous son of a famous father, and the Sheen family has enough tales to make ten Hollywood movies. The idol of the youth, Charlie is a star that has been shining for a few decades now.

Sheen Jr. was not one to shy away from sports betting and according to his ex-wife Denise Richards, Charlie was spending close to $200,000 a week on sports betting.

On top of being an avid gambler, Sheen was often involved in incidents that put him in the spotlight. She even went as far as to claim that he was making a bet while they were driving to a hospital for her to have labor. You can’t say anything about his dedication to the cause. 

Tobey Maguire

Tobey Maguire

Spiderman is Peter Parker, and the secret poker gambler is Tobey Maguire. Back in 2011, he was a part of secret poker tournaments that took place in New York and Los Angeles.

According to sources he won over $300,000 but the games were quite illegal, so he ended up on the wrong side of a multi-million lawsuit. He got away with a $80,000 settlement, but that’s quite a loss tied to gambling nonetheless. 


Celebrities are just like us; they can’t stay away from a nice gambling challenge. That’s fine, they’re humans too. As we said, the only difference is that they can lose more by a simple equation of having more to lose.

Also, they’re famous so the world loves to hear about both their wins and failures. It’s a good thing our losses remain known only to us and our dealers. Drake, Ben, and Tobey are not that lucky. 

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