matt damon, rounders, gambling, gamblers

Top Six Celebrity Gamblers – Matt Damon, Charlie Sheen & More

They’ve worked hard. These celebrities have earned their money, purchased private jets, luxury cars or yachts, invested in real estate, and bought anything their heart desired. So what else do they spend their money on? Gambling! It’s easy to see how celebrity gamblers end up spending their money playing cards and making bets.

Some of Hollywood’s most famous movie stars and celebrity gamblers reportedly not only enjoy playing best online casino games, but some of these gamblers could also be described as addicted to gambling and casinos, both online and land-based. Most of these celebrities prefer to play in the brick-and-mortar casinos – in public as opposed to playing online. Check out these Canadian online casino reviews, but be careful not to end up like the celebrities on our list!

Here are six famous celebrity gamblers.


Our first celebrity on the list is Tiger Woods, the pro golfer you’ve no doubt heard of – for both his skill on the golf course as well as his romantic entanglements. Tiger Woods is possibly the biggest name in golf, and he has a tendency for making big bets, as well. Rumor 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.


Remember the movie Rounders? It came out a while ago (1998), so you may not have seen it. 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 rumor has it he’s even connected to an illegal gambling ring, with games taking place in top-notch hotels and private residences with fellow stars like Leonardo DiCaprio, Ben Affleck and Tobey Maguire.


Like his friend Matt Damon, Ben Affleck is a keen card player who particularly loves blackjack and poker. In 2001, he reportedly lost a $400,000 hand of poker and eventually checked himself into rehab to help deal with his gambling problem. Another rumor 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. Wow! Check out what other famous celebrities are up to.


You’ll be hard pressed to find a more famous name in basketball or indeed any sport than Michael Jordan. He 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 businessman over a round of golf, and rumor has it Jordan’s gambling was the reason he retired from basketball.


Charlie 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 more than $200,000 a week to satisfy his cravings. It’s been said, however, that he’s since cleaned up his act.

6. 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 cool 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 clear sailing.


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