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Celebrities that Love to Gamble

The late, journalist Hunter S. Thompson once said of gambling, “There are many harsh lessons to be learned from the gambling experience, but the harshest one of all is the difference between having Fun and being Smart.”

These words ring so very true for most, but in particular for those who breathe in the rarefied air of being a celebrity. For over the decades, there have been big names who have crashed and burned in spectacular fashion at the roulette, blackjack or poker tables, all while in the public eye. On the other hand, there have also been many an image of some of our favourite celebrities winning big, and then some, at these very same tables.

We all love hearing about the lifestyle of the rich and famous, and many of our beloved celebrities are happy to allow us to peak behind the curtain and witness them gamble with amounts of money us mere mortals can only dream of.

There is a myriad of actors, musicians, TV stars and reality TV personalities cramming the casinos, packing the tables and indulging their love of gambling. Some of the big-screen actors and musicians that made it to this list are prolific gamblers who will not hesitate to place $100,000 or more in a single bet.

So, without further ado, let’s take a dive into the wonderful and crazy world of celebrities hitting the tables.

Ben Affleck

Perhaps better known for his romantic dalliances than his body of filmic achievements, Ben Affleck has, over the years, been a somewhat regular at the poker tables of the more elite casinos in Las Vegas.

Best known for his Oscar-winning screenplay for Good Will Hunting, as well as cringe-inducing performances in turkeys like Pearl Harbor and Gigli, Affleck resurrected his career behind the camera. Movies such as Argo and Gone, Baby Gone, firmly put him back on the map.

Besides his movie achievements and failures, Affleck never enjoyed anything more than sitting at a poker table, drink in hand, and gambling a fortune.

In 2001, he won $800,000 playing blackjack, and in 2004 he won $356,000 in the California Poker Championship. During his playing days, Affleck’s opponents included professionals such as Stan Goldstein and Chuck Pacheco, as well as actor Toby Maguire. However, since becoming sober, he seems to have stayed away from the poker tables.

Tobey Maguire

A relative unknown, starring in well-received independent movies, Tobey Maguire was thrust into the limelight with his era-defining role as Peter Parker aka Spiderman, in Sam Raimi’s massively successful Spiderman movies in the early 2000’s.

From there, it seemed nothing was impossible for this young actor. Instead of embracing the attention, Maguire retreated from the limelight and established himself as somewhat of a card-shark, turning up and killing at some of the most celebrity-heavy poker games in Vegas. This all culminated in 2011 when he won over $300,000 from the famous investor Brad Ruderman.

Brad Pitt

Wildly successful as an actor, Brad Pitt spread his talented wings as a producer under the banner of his Plan B production company, winning Oscars for ‘The Departed’ and ‘12 Years a Slave’, to name but a few. His personal life may have hit the headlines, but his talent on screen is undeniable, culminating in his Academy Award for Quentin Tarantino’s magnificent ‘Once Upon a Time in Hollywood’, in 2020.

During the filming of the enjoyable film, ‘Ocean’s 11’ and its two sequels, the Hollywood actor was so enamoured with all the kinds of gambling games, that he did not miss the opportunity to play slot machines or cards, even in between filming. Once the cameras were off and the filming ended, the passion remained.

Matt Damon

The talented Mr. Damon. This Boston-reared actor has astounded and rewarded viewers of movies for years. He has the innate ability to shift from mysterious outsider to all-out action hero within movies. When we think of Jason Bourne, we immediately think of Matt Damon. He is that believable.

An Oscar-winning screenwriter and Oscar-nominated actor, this guy doesn’t mess around. And that’s the same with his poker skills. As a member of the ‘Oceans’ crew, Damon has never shied away from the big game.

Ben Affleck’s best friend is even more passionate than Batman. The fact is that during the filming of the movie ‘Rounders’, he and Edward Norton were trained by the legendary player, Johnny Chan. To this day, Matt regularly appears in casinos and takes home the bacon quite often.

George Clooney

Another stalwart of the ‘Oceans’ film trilogy, George Clooney is a name and figure to be reckoned with. His immense film and TV biography is unparalleled as well as his production company’s award-winning and consistent out-put.

Not only is he an Academy Award winning actor and producer for such films like Syriana and Argo, he has established a $1 billion tequila company, as well as being a human rights ambassador for Southern Sudan.

George Clooney is not just a gambler, he even tried to open his own casino. He invested a significant amount of money in the construction of Las Ramblas in Las Vegas, but, unfortunately, his project did not materialise. As Danny Ocean, he will always have a bet.

Hugh Hefner

The ‘Hef’. Although contemporary reviews of Hugh Hefner are not in any way positive or, in any way favourable to him, it is undeniable that he had a huge impact on American culture throughout the 60s, 70s and 80s. Hefner’s Playboy Mansion was the bastion of Reagan’s money-cultured America. Shiny things and bikini-clad excess. He didn’t shy away from it, and neither did the rich and powerful.

Hefner played many gambling games and used to play not only for money but also for undressing. The businessman even had his own institution in Las Vegas – The Playboy Club & Fantasy Tower, and in the 60s he was the owner of a casino in London. It is said that in the best times of the London Playboy, its regular visitors were the Beatles, Woody Allen, and Rudolf Nuriev.

Jennifer Tilly

Commonly known and appreciated as the voice of the bride of Chucky and the lover of Gina Gershon in the wickedly great noir movie, ‘Bound’. The famous Hollywood actress is considered a semi-professional poker player. The hobby began with one television show in which she portrayed a poker player. Jennifer won a gold bracelet at the 2005 World Series of Poker and finished first place in the Ladies’ No-Limit Texas Holdem tournament.

Charles Barkley

An undeniable basketball legend, Charles Barkley is known to be a regular at the tables. As opposed to his success on the court, his times at the table is widely known to be unfortunate. It just goes to show that just because you are good with one thing, it doesn’t necessarily translate in to any other aspect of your life.

And so there you go. You may have millions in the bank and random strangers may scream your name if you walk down the road, but luck is luck. Good fortune is good fortune.

More importantly, you do not have to be a celebrity to gamble, whether at Queenplay or anywhere else. Just be sure to remain in your budget at all time, and with a bit of luck, you could one day be counted amongst the famous casino winners.

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