With the disposable income that most high-profile Hollywood celebrities have, it’s no wonder that many love to gamble as much as they do. Certain celebs have been known to be intimidatingly high rollers at the betting table and some are enviably successful with their risks, while others have lost millions as quickly as they made them. A few of these celebrities have even publicly admitted to having a gambling addiction, and subsequently sought help.
Some celebs love to put wagers on sporting matches, while many others hone their skills at the poker tables. The general public has been interested in the gambling habits of celebrities for some time: Both Bravo and the Game Show Network (GSN) produced celebrity-centric gambling programs Celebrity Poker Showdown and Celebrity Blackjack, receptively. Tournament winners on Celebrity Poker Showdown included Jason Alexander and Seth Meyers. Celebrity Blackjack ran for two seasons on GSN, and winners on the show included Caroline Rhea, who donated her winnings to Much Love Animal Rescue and Project ALS, and Dean Cain, who donated his winnings to The Malibu Foundation for Youth and Families. Of course, it’s not all smiling faces and charitable winnings in the realm of celebrity gambling. While a lot of the big shots on this list can afford to lose tens of thousands or even millions, some have gambled themselves into destitution. The late great Mickey Rooney, for example, once estimated he squandered away as much as $12 million because of his crippling gambling addiction. Will any of the stars on this list meet similar fates, or have they already? Read on to find out more about the vices of these ten well known celebrities who love to gamble the most.
10 Brad Garrett
Everybody Loves Raymond star Brad Garrett won the fifth season of Celebrity Poker showdown; he also played in the World Series of Poker in 2005, 2006 and 2007. His intimidating stature makes him a force to be reckoned with at the poker table.
9 James Woods
Woods considers his arch-rival in poker to be Ben Affleck, but Woods says he can read Affleck like an open book at the poker table. Gambling has been a part of Woods' life ever since he was a kid and would get sent to the bookie. Woods currently acts as a spokesperson for an online poker website, Hollywood Poker.
8 Norm Macdonald
This Canadian funnyman was so addicted to gambling back in the day that he wouldn't even cash in his chips. Instead he would just stash his winnings in his fridge and use them on his next trip to the casino. He said he has gone broke four times because of gambling.
7 Pamela Anderson
6 Ray Romano
Like his on-screen brother Brad Garrett, Ray Romano has also played in the World Series of Poker. Rather ironically, when he played in the tournament he was sponsored by cable network TNT to promote his now-cancelled dramedy Men of a Certain Age. Men of a Certain Age featured fictionalized elements of Romano's past problems with gambling addiction - Romano had to attend gambler’s anonymous because he had become addicted when he was younger.
5 Shannon Elizabeth
She may be an actress, but Shannon Elizabeth considers her poker playing to be a career as well. After competing in the 2005 World Series of Poker, Elizabeth played in a promotional tournament at Caesar's Palace where she beat 83 other celebs and won $55,000. She made it to the semi-finals in the National Heads-up Poker Championship where she defeated numerous high-profile world champion poker players.
4 Ashton Kutcher
According to Esquire magazine, Ashton Kutcher was once used as a front for the biggest sports betting syndicate in the United States. He said he was earning as much as $750,000 in four weeks by betting on college football; he reportedly took a 10% cut of those winnings. It was believed that Kutcher could have been charged with messenger betting, a practice that is illegal in the state of Nevada, but no investigation was ever launched into his alleged activities.
3 Tobey Maguire
This former Spider-Man took up tournament poker right around the time he started cashing big checks for playing the wall-crawler. Professional poker player Daniel Negreanu has helped Maguire develop his skills. Pro poker player Phil Hellmuth said that by 2007 Maguire had won $10 million thanks to his poker skills. Maguire has competed in the World Series of Poker numerous times, and he took home $39,445 in the 2007 tourney. Molly Bloom, a celebrity poker organizer who served a 1 year probation for organizing illegal poker games, has made some pretty outrageous claims about Maguire’s gambling antics. In her memoir Molly’s Games, she wrote that Maguire was a sore loser and poor tipper. She says he once attempted to make her bark like a seal for a $1,000 tip.
2 Ben Affleck
1 John Daly
A look at John Daly will tell you he's a man who indulges his vices. His affinity for placing bets and playing card games has led to his loss of inordinate amounts of money. He has said he gambled away over $90 million in 15 years of gambling binges. He did win some back, but it was a paltry $35 million in comparison. He would play as many as seven hands at once at the blackjack table, and he loved it when a crowd gathered around him to witness the spectacle.