8 Famous Celebrity Gamblers


What do you do when you have more money than you can count? The world’s rich and famous have found several ways to spend their wealth, some more sensibly than others. Real estate is usually a good investment, and many celebs like to bid their travel woes farewell by buying their own private jets. Some donate generously to charitable causes while others pursue big dreams like owning their favourite sports team.

Some celebrities though like to indulge in something we know all about – gambling! Here are a few famous faces you will probably recognize and might even spot at a poker table, trying to blend in.

Matt Damon

Do you remember that movie Rounders? It came out a while ago (1998) so it might be hard to recall but here’s a recap. A very young Matt Damon plays Mikey, a reformed gambler who returns to the poker table to help a friend make enough money to fend off his loan sharks.

In real life, Matt Damon is a huge fan of poker and has been connected to an illegal gambling ring, with games taking place in top-notch hotels and private residences with fellow stars like Leonardo di Caprio, Ben Affleck and Tobey Maguire.

Tiger Woods

The first (but definitely not the last) major athlete on our list, you have certainly heard of this star, as well as his various misbehaviours. Tiger Woods is possibly the biggest name in golf and he has a penchant for making big bets too. Rumour has it that Woods bets $25,000 per hand in blackjack and has had a $1 million betting limit enforced by the MGM Grand in Las Vegas.

Ben Affleck

Just like his friend Matt Damon, Affleck is a keen card player, particularly blackjack and poker. In 2001, it was said he lost a $400,000 hand of poker. He subsequently checking himself in to rehab to help deal with his gambling problem. Another rumour states that he once drunkenly wagered $60,000 on blackjack, coming away with $800,000 in total before leaving a generous $150,000 tip to casino staff.

Charlie Sheen

Mr Sheen always seems to be in the limelight for his vices, including womanizing, drinking and substance abuse. So, it comes as no surprise that Sheen’s ex-wife Denise Richards claims he had a severe gambling addition, regularly spending over $200,000 a week to satisfy his cravings. It’s been said however that he’s since cleaned up his act.

Michael Jordan

You’ll be hard pressed to find a more famous name in basketball or indeed any sport. Michael Jordan made his mark with the Chicago Bulls but his success in gambling has not matched his sporting prowess. Back in 1993, he admitted to losing $165,000 while gambling in Atlantic City. Jordan once lost $1.25 million to a San Diego business man over a round of golf. Rumour has it Jordan’s gambling was the reason he retired from basketball.

50 Cent

Rapper 50 Cent has made some pretty outrageous bets over the years, including a half a million bet on the New York Giants reaching the Super Bowl in 2012 and a full million on them winning the showpiece game. He won both bets in this case but with big numbers like those on the line, it’s not always plain sailing.

Pamela Anderson

She might be more famous for her acting on the large and small screens but Pamela Anderson also has an interest in gambling. In 2007, news reports said she had lost a quarter of a million in a single night, playing poker.

Ray Romano

Known for his role in ‘Everybody Loves Raymond’, Ray Romano had a serious problem with gambling, poker in particular. The tabloids reported that he once had to seek professional help after his betting addiction spiralled out of control.

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