Hollywood Gamblers - Celebrities Who Can't Seem to Stop Betting



Staff member
May 3, 2008
"I want people to understand, gambling is not a bad thing if you do it within the framework of what it's meant to be, which is fun and entertaining."

These words come from Michael Jordan, the American basketball star, celebrity, and a compulsive gambler. Luck has been kind to Jordan, and he's been making
enough money to be able to afford losing millions of dollars in reckless betting on golf games and in casinos.

The story is no different for many other celebrity gamblers hailing from Hollywood. They make so much money that it makes sense for them to gamble in millions.
Let's take a look at some top Hollywood gamblers and see what they've been up to.

Brad Pitt and George Clooney:
Arguably the most handsome men in Hollywood, the duo is perhaps among the richest celebrities as well. If you have any doubts about their wealth,
consider this: The two "Ocean 11/12/13 costars have jointly invested some $3 billion in a Las Vegas casino complex. If you own the casino, you can never lose.
The two of them seem to be getting ready for a never-ending winning spree.

Matthew Perry:
The Canadian-born "Friends" sensation loves to gamble when he's with friends. Poker is his thing and he's good at it. It's quite a spectacle watching him and his poker-buddy and
costar David Schwimmer matching bets as well as wits in the American Celebrity Poker Showdown. Their jokes are even more entertaining than the game itself, and pull spectators to their table.

Ben Affleck:
The controversial Batman miscast is reputed to be addicted to gambling, poker mainly. He's also reported to be running a secret poker ring with other bigwig celebrities being the members.
Affleck also faced marital issues with his wife and "Daredevil" costar Jennifer Garner, but everything seems to have worked out for the best between the two of them.
Ben has a habit of winning his bets and had pocketed $356,000 in the California State Poker Championship in 2004, the same year in which he married Jennifer.

Matt Damon:
The "Bourne Identity" star is rumored to be a member of Affleck's secret poker club. Although famous for his role in the high-stakes underground poker movie "Rounders",
the celebrity likes to keep his real-life penchant for poker under covers. Looking at his baby face, no one can guess that Damon is really smart at poker,
other than his fellow players Ben Affleck and Leonardo DiCaprio.

Shannon Elizabeth:
There have been rumors that the "American Pie" beauty runs a gambling ring from her home, but nothing substantial has come out.
The American tax watchdogs have been sniffing around for evidence, but they found none. Meanwhile, Shannon won $11,000 in the Seminole Hard Rock Poker championship last year.
She's been abundantly photographed stacking chips on poker tables, and looks stunning enough to distract her opponents.

Charlie Sheen:
The "Two and a Half Men" star was spending around $20,000 a week on sports betting at one point in his life. This was revealed by none other than his ex-wife Denise Richards,
and was one of the reasons why Denise filed for divorce in 2006. His marriage has ended, but his gambling habit hasn’t.

Toby McGuire:
It seems superheroes are as much into gambling as us ordinary humans. The "Spider Man" hero was sued for being a member of a multi-million dollar gambling circle that was, of course, illegal.
He paid $80,000 to settle the lawsuit, but hasn’t stopped gambling. His name surfaced again last year, in connection with high stake poker games being played at his home.

The list of Hollywood gamblers goes on, but it still doesn’t include many celebrities who gamble more discreetly. After all, if celebrities wouldn’t gamble, who would?
  • Like
Reactions: Kotsy and Ellis


Well-Known Member
May 5, 2008
I wonder how many of them gamble online?
Now that would be a Hollywood story.

Yukon Gold Casino