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a look at celebrity gamblers

A Look at Celebrity Gamblers

If you've ever spent any time in Las Vegas, you've probably spotted at least a couple of Hollywood heavyweights, sports superstars, and internationally known comedians on the strip. With an insatiable taste for the good life and more disposal income than you probably make in a decade, many celebrities love gambling. Plus, who can resist the vibrant atmosphere that is the city's trademark, especially if you can afford it? Keep reading as we rundown the biggest celebrity gamblers along with their trials and tribulations at the tables.

Charlie Sheen

While most people are familiar with Sheen's work in Two and a Half Men, Platoon, and Major League, many people don't realize he's also a compulsive gambler. Perhaps his big time bets were overshadowed by his heavy drug use and sexual escapades. The actor not only used to wager $20,000 weekly on sports, but he once placed a million-dollar wager and lost. We're not sure if that was during his trademark “winning” phase.

Shannon Elizabeth

Best known for playing Nadia, the sultry foreign exchange student in The American Pie films, Shannon Elizabeth has proved time and time again that gambling isn't just for the boys. Shannon is probably the country's best known female celebrity poker player after competing in the 2005 WSOP Main Event. She managed to cash four times in 2006 and 2007 events too. While she's still active nearly a decade later, most card players remember her from the NBC National Heads-Up Poker Championship where she reached the semifinals.


Michael Jordan

Did you know Air Jordan's fame stretches beyond the hardwood and onto the casino floor? During the 1992 Olympics in Barcelona, Jordan routinely played poker until the break of dawn, sacrificing sleep even with gold medals on the line. The hall of famer also bet his teammates on who would get their luggage first at the airport. Yet Michael Jordan the gambler might be best known for losing $5-million playing craps in Las Vegas or racking up a $1.25-million debt placing golf bets.

Ben Affleck

The caped crusader is widely known for bringing his heroics to the blackjack and poker tables, much to the dismay of many casinos. Affleck was so successful at blackjack that the Hard Rock Casino banned him from playing after winning close to a million bucks during two visits. Despite his winning track record, his former wife Jennifer Garner was equally unimpressed, if you believe the divorce papers. Poker fans may recall that Ben won the California State Poker Championship in 2004 and appeared in a WPT final tourney the same year.

Michael Phelps

The most successful athlete in the history of the Olympics has plenty of talents outside the pool. The fabled swimmer is famous from his marathon gambling sessions across the USA. Phelps has been known to drop several hundred thousand dollars at the poker tables, which is a far cry from the low stakes poker he used to play online when he first discovered the game. While friends and family were once concerned about his seemingly reckless gambling and drinking, it clearly hasn't affected his performance in the water.

Charles Barkley

The former basketball all-star's gambling obsession is a matter of public record. Barkley has admitted to losing a million dollars more than 30 times in his life, including a $2.5 million loss playing blackjack over the course of six hours. He also estimates that he's down in the neighborhood of $10 million in his lifetime. That figure includes big wins wagering on sports and playing poker. Fortunately for his wallet, he's found work as an on-air analyst.

Pamela Anderson

Pamela's poker skills aren't particularly strong. The blonde bombshell is reported to have lost a quarter of a million dollars to Antonio Esfandiari in a single Sin City session back in 2007. Whether or not the rumors of Anderson paying off a gambling debt with sexual favors are true, there's no denying that the Baywatch star loves the atmosphere in Las Vegas.

Toby McGuire

Toby takes the game of poker so seriously that he's willing to lug around a $17,000 shuffling machine. While critics have called him obnoxious and a sore loser, the Spider-Man star has had little trouble spinning webs around the competition. McGuire is widely known for regularly winning $50,000 or more in a single night.

Ashton Kutcher

The star of Dude Where's My Car might have trouble keeping track of all the money he's won from his various ventures including gambling. Kutcher was once the face of the biggest sports betting syndicate in the USA. According to an Esquire interview, a group of statisticians figured out how to work changes in point spreads to their advantage and hired the actor to secretly place bets on their behalf. After paying out millions to Kutcher, who sportsbooks assumed was a wealthy albeit clueless actor, they ultimately refused to accept his bets.

Jennifer Tilly

Anyone who has ever watched poker on late night television, has surely seen The Canadian-American actress at the tables. While Tilly is famous for her signature look that is heavy on push-up bras and low-cut shirts, she's always got the moves to match. Jennifer is a WSOP bracelet winner, having conquered the 2005 Ladies' No Limit Texas Hold'em event. She's also made her mark at various WPT events, the Celebrity Poker Showdown, and the Game Show Network's Poker Royale. She's racked up close to a million bucks over the years.

Tiger Woods

The man who brought golf into the mainstream is a bigtime gambler. He's been seen in Vegas alongside Charles Barkley and Michael Jordan, but could easily give those ballers a run for their money. Woods is well known for his $25K blackjack hands and is the proud owner of a million-dollar betting limit at the MGM Grand. Some pundits have estimated his lifetime losses in the $50-million range, yet that's not a big deal for someone whose net worth easily tops seven figures.

50 Cent

The man whose birth certificate reads Curtis James Jackson is an avid sports bettor. The rapper not only bets millions on football, boxing, and other pro sports, but he's not afraid to brag. He frequently posts his betting slips and stacks of cash on social media. Whether or not he's up or down overall, he did make a fairly lucrative bet on Vitamin Water that paid out handily in addition to his rhyming skills.

Alan Iverson

The 11-time basketball all-star has had less success off the hardwood. Iverson, who is known for having gambling and drinking problems, has been banned from casinos in Detroit and Atlantic City. Sadly, Iverson was on the verge of insolvency despite having racked up over $200 million in lifetime basketball earnings.

Aaron Paul

The actor who played Jesse Pinkman on Breaking Bad also loves to play poker. Aaron Paul recently competed in the 2015 World Series of Poker and Global Poker League's Summer Series Kickoff. Unfortunately, Aaron Paul's television and film schedule keeps him away from the felt.

Gladys Knight

The singer whose discography includes chart toppers like If I Were Your Woman and Midnight Train To Georgia became addicted to gambling while performing at casinos. Gladys was notorious for playing blackjack all night long and neglecting her son in the process. These days she thanks her faith and Gamblers Anonymous for helping her break the habit.