Movie Stars Who Love To Gamble

Space Jam

Like us mere mortals, some celebrities can’t help but take a punt from time to time. Just because they’re multimillionaires doesn’t mean they don’t have their own vices! However, with much larger bankrolls available, inevitably their stories are much more exciting.

There really are no shortage of A-listers who love a roll of the dice, a few hands of blackjack, or even wagering on whether their suitcase will get off the plane first. Here are some of the better tales from celebrities who love to gamble.

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Ben Affleck

The star of Justice League and Armageddon might like to keep himself to himself generally but every now and then some juicy titbits emerge about one of Hollywood’s finest. According to tabloid reports, Affleck was banned from playing blackjack at the Hard Rock Hotel & Casino in Las Vegas because he was beating them too heavily. He said:

“I took some time to learn the game and became a decent blackjack player. And once I became decent, the casinos asked me not to play blackjack. I mean, the fact that being good at the game is against the rules at the casinos should tell you something about casinos.”

The words from the gambling flick Runner, Runner star’s mouth run contrary to media reports that ex-wife Jennifer Garner left him over his drinking and gambling habits. However, it seems strange that the casino would ban a multimillionaire from playing blackjack unless he was seriously taking it to the house!

Michael Jordan

Michael Jordan was and probably still is an absolutely prolific gambler. The basketball star of the 1990s used to bet on absolutely everything. A former teammate told a publication that the six-time NBA champion would routinely bet as much as $100k on rock, paper, scissors games against friends. However, the original Dream Teamer used to like to bet on other ludicrous things too. Take his proposition bet against team mates after his first trip to the Olympics. The squad were waiting for their luggage to make it off the plane when Jordan bet $900 that he’d be the first with his suitcase in hand. That time, he won. Even if it was pocket change to him!

Jordan wasn’t so lucky against the San Diego Sports Arena manager Richard Esquinas, however. The story goes that he lost $1.3 million over the course of a ten-day golfing trip. His “Royal Airness” managed to worm his way out of paying most of it though. He eventually settled by paying Esquinas just $300,000.

Charlie Sheen

Sheen loves just about everything that your grandmother would hate. He drinks, takes drugs, and sleeps on top of a large pile of money, with many beautiful ladies. It’s therefore no surprise that the multimillionaire star of Two and a Half Men would also have a penchant for flirting with lady luck. Although he claims he no longer gambles, his ex-wife Denise Richards claims that the “bi-winning” wild man would spend more than $200,000 a week to satisfy his urge to gamble. Well Charlie, if you’ve got it, why not flaunt it!

Matt Damon

Matt Damon is another A-list movie star who loves a punt. Like his good friend Ben Affleck, Damon was the star of an early gambling movie himself. Rounders was all about a gifted poker player trying to save his friend from debt collectors. However, in real life, it appears Damon wasn’t so lucky.

Reports exist that Damon and Affleck used to attend private poker games for high stakes in hotel rooms. Now, there’s nothing too dodgy about that. We’re sure many Hollywood stars like to play a game away from the prying eyes of the public, keen to get a glimpse of red carpet royalty. However, it later transpired that the organiser of these games had embezzled his buy in from a hedge fund he was supposed to manage. Many of the winners of the games were later mentioned in court. However, the fact that neither Affleck, nor Damon were personally named suggests that lady luck wasn’t on their side those evenings.

These days, Damon prefers to play amongst friends and likes to keep the buy ins for these private, invite-only games lower. That’ll be just $100,000 a head then!

Pamela Anderson

Ever wanted a night of passion with the blonde bombshell that is Pamela Anderson? Well in 2007 it might have been possible – if you had $250,000 to spare that is. Rumours abound that Anderson racked up a quarter of a million-dollar debt to legendary poker player Antonio “the Magician” Esfandiari. Rather get her purse out, this was settled with a night of passion instead. The two later had something of fling together. Here’s the tale from the horse’s (sorry Pammy) mouth:

“I was playing poker one night… and I was down about 250 grand. He said if I made out with him, that would clear the [bet… I paid off a poker debt with sexual favours and I fell in love. It’s so romantic.”

As well as literally staking her body at the felt, Anderson later launched her own online poker game back in 2012. Presumably, none of the players got as lucky as Antonio did that night!

There are certainly others that could make this list. Celebs tend to try and hide this side of their lives and while some take a risk and win. Others aren’t so lucky.



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