Celebrities with Gambling Issues

Ben Affleck:

Academy award winner Ben Affleck has a gambling record that dates back as far back as 2001 when he lost thousands to a Hollywood studio executive, which lead to a stint in gambling rehab. More recently he has been in the news for his appearances in high stakes blackjack games. In addition, to his gambling prowess, Affleck has landed in hot water over allegations that he was counting cards, these accusations he would eventually confess to. The “Gone Girl” actor now banned from playing Blackjack in Sin City.
ben affleck

Michael Jordan:

There are endless gambling stories about the six-time NBA Champion from the Chicago Bulls. Jordan’s gambling problems are well documented over the years, from owing millions of dollars to bookies to going to Atlantic City before a game, MJ along with his ultra-competitive personality, has never been scared to walk away from a high-stakes poker game.
Michael Jordan

50 Cent:

Rapper 50 Cent placed a $1.6 million bet on the Floyd Mayweather vs. Manny Pacquiao fight last week, yet this is just one of many examples that makes 50 Cent one of the most notorious celebrity gamblers on this list. The American-born rap icon is mostly known for placing large amounts of cash on sporting events and is a mainstay along the Las Vegas Strip.

David Bentley:

Admitted obsessive gambler David Bentley is the first footballer to make this list. The Tottenham Hotspur says he started placing small bets at the age of 14 and from there gambling took up a huge chunk of his life off the pitch. His gambling habit was so bad at one point he was placing over 100 bets per day, he almost had to end his career prematurely.

Charlie Sheen:

Mr. Tiger Blood had many addictions that included sex, drugs, alcohol and gambling! Sheen is a hardcore gambler, he is known for throwing down tons of money at the tables and also betting on sports. His ex-wife Denise Richards said that former Two and a Half Men star was spending about $200,000 a week on sports bets. Recently, Sheen has stopped gambling but his other harmful habits such as drug abuse has Sheen living life on the edge. The many sides of Charlie Sheens volatile personality has been featured in the tabloids and on entertainment networks around the world.
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Charles Barkley

Former NBA All-Star and current TV personality Charles Barkley has a past history of degenerate gambling that has put the Hall of Famer into serious debt. Barkley has admitted to losing over $10 million at casinos throughout his professional life as a basketball player.

Shannon Elizabeth:

You may recognize her as Nadia from the American Pie Franchise, but I bet you didn’t know that the actress also has a successful career as a poker player. She is considered one of the best celebrity poker players and has made a few appearances at The World Series of Poker.

Tobey Macguire:

Away from the big screen Tobey Macguire spends much of his time at the poker tables. The former star of the Spiderman movies is known for playing high stakes games of Texas hold’em. Macguire was pursued by a fund’s manager, claiming the actor took him for $5.2 million illegally. He was sued and ended up paying a $80,000 settlement.
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Matt Damon:

Similar to Tobey Macguire, the Bourne Identity actor has always been accused of participating in an illegal gambling ring. Damon has appeared on celebrity poker games normally playing Texas hold’em with some of his celebrity friends. To prepare for the gambling film Rounders, Damon spent quality time at the tables so he can learn ins and outs of being a high stakes poker player.
matt damon

Pamela Anderson:

When Pamela Anderson comes to mind you probably think of Baywatch or her time spent as a Playboy bunny. But what you probably don’t realize is that Anderson loves to gamble she especially enjoys playing poker over slots. There are rumors that the Baywatch paid off a $25,000 debt by asking for sexual favors.
pamela anderson