Hollywood’s Most Notorious Gamblers

When it comes to high stakes gambling, it’s certainly easier if you’re a famous millionaire. Celebrities have always been drawn to gambling, either because of the extra thrills they can find at casinos or simply because, with their money, they can afford to play.

In fact, casinos have been inviting famous Hollywood celebrities to their openings, events and high-roller tables for decades. It’s ideal for everyone, as the actors get to play excellent high-stakes games while other players can brag about playing poker with a movie star. Of course, some Hollywood stars need less convincing than others, and a few notable names have been more than happy to join in on any gambling action.

Charlie Sheen

Many details of Sheen’s personal life came out when he split from his wife Denise Richards. One such personal detail was that the actor bet on sports every day, with highs and lows in the hundreds of thousands of dollars. He was also apparently a bad loser, with violent mood swings when wagers didn’t go his way.

Following his public meltdowns Sheen started a gambling site, although he’s since said that he’s cutting back or stopping gambling altogether. His reputation as a bad boy means he might always be associated with his vices, though.

Ben Affleck

Back in 2014, Affleck was banned from the blackjack table at the Hard Rock Hotel & Casino in Las Vegas. While reports at the time claimed that he was counting cards, he insisted that he just got really good at the game. Either way, he clearly spent a lot of time honing his abilities, gambling for extended periods in Sin City.

He disputed the idea that he had a gambling addiction, though, saying that casinos don’t tend to kick gambling addicts off the tables for being too good at the game. Blackjack is his only game, and he doesn’t wager on sports or other casino games.

Ben Affleck having fun at the poker table
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Matt Damon

The cult movie Rounders (1998) shows Matt Damon as a proficient gambler, something he would continue to play in his role in the Oceans 11 franchise. He actually did learn some card skills in order to prepare for the role, which prompted him to develop a rather healthy interest in playing poker off camera as well.

While he continues to play poker in high-stakes rooms and private games, he’s known for being understated and polite. He isn’t one of the rowdy Hollywood gamblers, but rather a down-to-earth guy who enjoys betting on a good hand of cards.

Pamela Anderson

Back in 2007, Anderson told Ellen Degeneres that she was playing poker and ended up down $250,000. Her male opponent said she could clear the bet if she made out with him. She joked that she paid off a poker debt with sexual favors and fell in love. This tallied with reports of her marriage to, and subsequent divorce from, Rick Salomon, formerly of Paris Hilton sex-tape fame.

It’s hard to say if she’s keeping her gambling under wraps now, or if marrying someone to pay off poker debts is keeping her from the casino tables these days.

Pamela Anderson playing poker
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Ray Romano

Four years after the end of Everybody Loves Raymond, Romano hoped to be taken more seriously in his career. That’s part of why he took on the role of a compulsive gambler in Men of a Certain Age – or was the character made that way because Romano was himself a gambling addict?

Romano did in fact admit that he had a gambling problem, which ended up being a key part of his character. He got help for his addiction, and also competed in the World Series of Poker. He also continues to make “virtual bets” when playing golf.

Shannon Elizabeth

Made famous in her role as foreign exchange student Nadia in American Pie (1999), Elizabeth has gone on to do well at the poker tables. She is known as a formidable opponent, winning big and playing hard with the rest of them. With notable wins at the World Series of Poker, as well as great standing in online poker rankings, this star means business.

Shannon Elizabeth laughing with Phil Ivey at the poker table
Image Credit: seminolehardrockpokeropen.com

Tobey Maguire

Back in 2011, Maguire settled a lawsuit following his involvement in illegal high-stakes poker gaming. But the organizer of those games said that he was generally not a good sport when it came to his gambling habits. He was rude, a sore loser, and even told her to bark like a seal if she wanted a tip.

Staying largely out of the media these days, it’s unknown if he has switched to only playing private games or if he’s given up poker altogether. But with the book and subsequent movie Molly’s Game (2017) highlighting his less than stellar character at poker games, his poker antics will probably end up in the spotlight more than he’d like.

Tobey Maguire competing at the World Series of Poker
Image Credit: nypost.com

Walter Matthau

Originally making a name for himself in movies like The Odd Couple (1968) and Charade (1963), this classic movie actor continued to act well past typical retirement age in ’90s comedies like Grumpy Old Men (1993) and Dennis the Menace (1993). But he wasn’t just a movie star – he was also an avid gambler.

He preferred to wager on sporting events, particularly on basketball or horse racing. While he wasn’t a big fan of Las Vegas’ casino action, he admitted that it was hard for him to walk past a craps table without trying a few rolls of the dice.

Walter Matthau was a movie star and avid gambler
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