10 Celebrities That Can’t Get Enough of the Casinos

By in Casino & Gaming on
6 Minute Read

One of the great things about casino gambling is that it reaches such a broad-ranging demographic. Players—young and old and rich or poor—flood the casinos daily.

That means you never know who you could bump into on the tables. You may find that “Larry from Omaha” is the most interesting man in the casino.

However, you could find yourself rubbing elbows with a Hollywood starlet or famous athlete. Here are 10 celebrities that can’t get enough of the casinos.

1 – Ben Affleck

There has been a ton of gossip about Affleck and his alleged gambling problem. I don’t see how enjoying the tables is a problem or anyone’s business personally — especially when you’re as good as Affleck has shown to be in the casinos.

A lot was made of when the Hard Rock Casino placed a long-time ban on the film star. People assumed that he must’ve created a massive problem or acted like an entitled brat, as is a common misperception of celebrities.

The fact is that Affleck has such a remarkable memory that he’s able to count cards without the help of a team successfully. This is what lead to his ban and not any nefarious behavior.

Affleck ultimately took the casino for over $1 million playing real money blackjack. Though they levied a ban on the actor, it was a ban on blackjack and not a blanket ban.

Affleck is free to play baccarat or poker, which he enjoys immensely. He also can play in just about any other casino on the planet with impunity, for now.

2 – Charles Barkley

Sir Charles is indeed a larger-than-life character wherever he happens to be. The former NBA All-Star is now a lead analyst for the NBA on TNT.

Not coincidentally, DraftKings came on board as a significant sponsor for 2021. Barkley seems delighted with the partnership, as should DraftKings.

Barkley boldly issued a $100k bet on the NBA’s opening nights that the Golden State Warriors would make their return to the NBA Finals.

Barkley is a notorious casino gambler, and it’s estimated that he’s lost over $10 million through the years. Some of this has landed him in hot water with the casinos fighting Barkley for their money.

He was also involved in a lengthy lawsuit that involved over $400,000 owed to a famous Las Vegas casino. Barkley paid his debts and is currently in good standing with the Vegas casino.

Sir Charles is a massive fan of the casinos, and he’s boasted about his losses before. He was mentioning that it’s a form of exciting entertainment that he can afford.

3 – Shannon Elizabeth

Shannon Elizabeth made a name for herself as the beautiful foreign exchange student in the American Pie movies.

However, the actress has chops that go way beyond her looks or acting skills. 

Playing Blackjack

Elizabeth began playing poker after she achieved massive fame from her roles. It turns out that she’s better than good; she’s excellent.

Shannon has competed in many of the world’s top poker tournaments and made final tables in these televised events.

The actress seems to love the game immensely and has made well over $325k in her poker career.

4 – Brad Pitt

The decorated actor first began casino gambling during the filming of Ocean’s Eleven. He was so enthralled with his new favorite hobby that castmates would regularly see him at the casino tables or slot machines during breaks.

The passion didn’t end there for the star. Pitt regularly enjoys casino trips with friends. However, his gambling has slowed down considerably.

I can’t imagine Brad Pitt walking over and taking the chair next to me at the blackjack table. I wouldn’t know if I was getting “Punk’d” or on-site of the latest Ocean’s movie.

5 – Tiger Woods

Tiger may be one of the most famous athletes on the planet. He’s also among the wealthiest athletes of all time.

Woods has demonstrated time and again how strong of a competitive streak he has and strives to win at everything he does. This deep desire to win is possibly what has made him the greatest golfer of the last 40 years.

You can make a strong case that Tiger is the best ever to do it.
Tiger has amassed a net worth of nearly $1 billion. So, there’s no question that he has plenty of disposable income.

Woods is known to enjoy playing high-limit blackjack on the high roller and VIP lounges in casinos worldwide. The community as a whole is pretty tight-lipped on how much Tiger is winning or losing during these sessions.

Still, we all know the house edge and can only imagine what the wagers must look like. Then again, Tiger rarely loses, and I can imagine he has the same fire on the blackjack table as he does on the golf course.

6 – Jennifer Tilly

Jennifer Tilly has had her ups and downs in the casinos. The actress became one of the top female poker players on the planet.

Tilly is one of the select few on the planet that has won a World Series of Poker bracelet. She accomplished the feat in 2005 after she knocked out over 600 competitors in the Ladies’ No-Limit Texas Hold ’em event.

However, in the following years, she retired from the game. She was noting that the dream of poker excellence is elusive.

Tilly was back within a few years and has earned close to $1 million in her professional career. Clearly, the time away from the casinos helped Tilly tune her game.

Tilly has continued to have her highs and lows but doesn’t seem to be able to avoid the casinos for long, which is excellent news because Tilly isn’t afraid to go head to head versus the men.

7 – Tobey Maguire

Maguire may be known best as the web-slinging hero Spiderman to many, but it’s his love for slinging poker chips that put him on this list.

Maguire is a regular in celebrity poker tournaments. The movie star is also regularly spotted in Las Vegas poker rooms and as a participant in the World Series of Poker.

Casino Games

The famous actor also enjoys playing with his movie star pals. He was heavily implicated in an investigation into an underground poker ring that involved dozens of Hollywood’s power players.

Apparently, Maguire was deeply involved in the operation. Unfortunately, law enforcement busted the ring for the stars, and the players were forced to find other, more legitimate games.

8 – Ray Romano

Ray Romano is among the most successful comedic television actors of recent memory. His hit show “Everybody Loves Raymond” was on air for nine seasons.

Romano is known to be found in the poker rooms in Las Vegas and Atlantic City. He’s another of the regulars on the celebrity poker circuit. He has carved out some wins against his famous fellow faces.

Romano has carried the knowledge and skill he picked up to compete in several World Series of Poker tournaments. The comedian hasn’t earned a coveted bracelet for his efforts but did cash in one event.

This earned Ray over $18,000 or approximately $1,782,000 less than he made per episode for his television show.

Ray’s not likely to switch careers anytime soon, but he can clearly hold his own at the poker table.

9 – Pamela Anderson

Pamela Anderson shot straight to stardom when she landed her role on Baywatch. The show had been on for a few seasons when Anderson joined the cast in 1992, but her addition pushed the popularity of the show over the top.

Sprinting down the beach in a red swimsuit isn’t Anderson’s only talent. The actress is an avid card player.

She met former husband Rick Salomon playing in poker games. It’s rumored that the two actually married after Anderson lost a bet to Salomon.

Whether or not a losing poker hand was involved in the eventual nuptials remains murky. One thing is evident, Pamela is a strong force at the poker tables.

10 – Michael Jordan

His Airness is the greatest basketball player in the history of the game. Jordan won six titles with the Bulls and earned himself six Finals MVP titles.

He has a competitive streak that rivals Tiger Woods. These two seem to be able to will themselves to victory on and off the field of play.

Jordan’s gambling antics are well documented. From losing a million-dollar bet on a single hole of golf to betting teammates $100k on his bags being the first ones to arrive at baggage claim, MJ loves to gamble on anything and everything.

By the way, Jordan won the $100k bet on the luggage. However, he later admitted that he paid the baggage handlers to ensure his bags would be the first ones through.

Jordan loves to visit the casino’s VIP rooms, and the action is always hefty.


These 10 celebrities that can’t get enough of the casinos are playing for stakes that sound ridiculous to many of us. Still, their bankrolls are so incredibly high that the action must be enormous for them to get that same thrill many of us get from a $100 bet on the tables.

Michael Stevens

Michael Stevens has been researching and writing topics involving the gambling industry for well over a decade now and is considered an expert on all things casino and sports betting. Michael has been writing for GamblingSites.org since early 2016. ...

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