Celebrities Who Love to Gamble

Icy Canada Team
Icy Canada TeamMarch 27, 2022
Updated 2023/09/08 at 9:32 AM
Tiger Woods winner at the US Open in 2002
Tiger Woods winner at the US Open in 2002. Source: Depositphotos

Gambling is many things to people; a source of entertainment, a way to make money, et cetera. It is something that has taken hold of the lives of many. 

When we talk about gambling, what comes to mind are regular people getting in on the action at the casino. But that’s not the whole picture. There are high-profile celebrities who love to get entertained at the brick-and-mortar. In this article, we’ll examine some of the biggest gamblers in entertainment:

A player plays roulette in a casino. Close-up hand with chips on a roulette table. Gambling.Casino game concept.
A player plays roulette in a casino. Close-up hand with chips on a roulette table. Gambling.Casino game concept. Source: Depositphotos

Roulette Players

Roulette is a game of chance, and its unpredictability is why many people love it. There are different roulette betting options online, and you’ll also find different wheels at land-based casinos. 

Roulette is no stranger to high-profile names. Tiger Woods, one of the world’s most renowned golfers, has been spotted at the Sin City Casino in Las Vegas spinning wheels. One time, he was pictured with another sports legend, basketball Hall of Famer, Charles ‘Chuck’ Barkley. Chuck is an avid and outspoken roulette lover.

Slots Players

Slot games are one of the oldest casino games. We can count back to more than a century since the advent of slots. People have always had a reason to enjoy slots, from the earliest slot machines to modern-day technological devices. It’s a people’s favorite. 

Slots are one of, if not the most, addictive casino games. Something about the machines makes even the biggest of celebrities like Pamela Anderson come back for more. Anderson is a former Playboy model known for our sexually appealing magazine photoshoots. But she’s also an avid lover of slots and is said to have gambled away some significant cash. 

But she’s not alone in this category. We cannot but include TV star David Gest, now deceased. Gest was reported to have blown away so much money that he ran up debts of up to $500,000 playing slots.


Blackjack Players

You can’t list three casino games without blackjack. It’s one of the most classy games, so it’s no wonder why it’s a celebrity favorite. Blackjack is the game celebrities are known to play the most.

And who are we to write an article on celebrity blackjack lovers without mentioning Ben Affleck? It would be almost sinful to omit his name. 

Ben got banned from playing blackjack at the Hard Rock Casino in Las Vegas. Why? Because he was winning too many games. He was accused of card counting. Although a legal blackjack strategy, casino owners frown at it.

And then there’s Tiger Woods, who seems to be a big roulette lover and a blackjack fan as well. Woods doesn’t love to compete on the golf field only; he also spends his free time hitting the casino. A report from one of his former mistresses claims he has gambled ten thousand dollars on blackjack.


Poker Players

Every celebrity who gambles loves poker. One such is Tobey Maguire, an actor most famous for playing Spiderman. Tobey reportedly paid a poker professional to learn the best techniques. Leonardo DiCaprio and Orlando Bloom are a few names that love poker. 

But we won’t end this section without acknowledging Jennifer Tilly and, of course, Ben Affleck. These two have competed at the highest levels, even on the World Stage. In 2005, Tilly won the World Series of Poker Ladies Championship and took home a poker bracelet and $158,625. Affleck won the California State Poker Championship in 2004, walked home with a whopping $365,000, and qualified for the World Poker Tour tournament.



The gambling industry has attracted a long list of celebrities, many more than we’ve listed. This shows that famous people are like us when it comes to loving the entertainment that casino games bring.

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