Celebrities are celebrities because they have a knack for staying in the news. What better way to do that than be seen in the glitziest casinos in Vegas, Atlantic City, or Monte Carlo? It does not matter whether they win or lose, as long as the amount is in millions. Frank Sinatra’s tryst with gambling is legion, but aficionados would be more interested in gambling celebrities of the present times. Here is our pick of the biggest five.
Ben Affleck would not probably be on the biggest winners (or losers) list, but his being evicted from the blackjack tables of Hard Rock Casino earns him big celebrity gambling points. The actor-director, who once starred in Runner Runner in which he took on a fictitious empire of online casino websites, is known to be a top-notch blackjack player.
The 2013 story, confirmed by Affleck, is that he was counting cards to improve his chances of winning at blackjack. He considers this to be a legitimate skill. Unfortunately, casinos in Vegas are permitted to ban players who are keeping mental track of the cards dealt. The casino security sidled up to him and said, “You are too good at the game.” They requested Affleck to enjoy gambling at any other game and when the celebrity refused, Affleck and his wife Jennifer were escorted to their car.
Affleck continued playing at other Vegas casinos. Recently, he was staying at the Wynn while in Sin City for a movie and was often seen at the high roller tables till 3 am. The tabloids then recirculated his earlier gambling escapades.
The heiress to the Hilton chain was born into the lap of luxury and has so much moolah that she cannot spend it fast enough. Gambling at the hot spots is the best option because it also gives Paris Hilton the visibility she desires.
Paris took to gambling early in life. At 19, she was doing the high-stakes, underground NYC poker circuit with Leonardo DiCaprio. Rick Salomon, with whom she made the infamous sex tape, was a successful, professional poker player. The amount of money won and lost never mattered to Paris, but she definitely rued losing her beloved, customized Bentley in a poker game in 2006.
This socialite is certainly no stranger to the exhilarating world of gambling. She frequents several Las Vegas establishments when she’s not too busy keeping up with her social calendar. If it’s not already jam-packed with luncheons and extravagant shopping sprees, she fills what might be left of her daily schedule playing online casino games which you can do for free using Pokie Pop bonuses – especially on days you feel lady luck is on your side.
The story of Toby Maguire is different from that of Paris Hilton in a couple of material ways. Maguire’s was a rag-to-riches tale and enough has been said about his impoverished childhood. His engagement with gambling has been more as an organizer than as a player.
Maguire shot to fame as Spider-Man in the blockbuster franchise, but of late has been staying away from films. However, he cultivated many Hollywood friends who have been partners in high-stakes gambling. Maguire was a skilled poker player himself but made the bulk of his money organizing poker games for the likes of Ben Affleck, DiCaprio, and Matt Damon.
It is said that this part of Maguire’s life was displayed on celluloid in the film Molly’s Game through the character Player X. In her memoirs Molly Bloom has revealed other incidents about this celebrity gambler. The one most talked about is Maguire asking Molly to bark like a seal for a thousand dollars. Of course, any publicity is good publicity for maintaining celebrity status.
Charlie Sheen was at one time the highest-paid American actor for the series Two and a Half Men, and he was the fastest to reach 1 million followers on Twitter. This is enough to establish his celebrity status. However, Sheen is infamous for his controversial lifestyle which includes womanizing, alcohol, and gambling.
His gambling addiction was first revealed by his ex-wife in 2006 during their divorce proceedings. Denise Richards claimed that Sheen would spend € 200,000 a week on sports betting and casino gambling. Even while going to the hospital for the birth of their child, Sheen’s mind was on gambling and he called his bookie to bet on a sporting event. This compulsive gambling was one of the reasons for the divorce suit.
There is another story of a very big win that elicited no celebration, not even a reaction, from Sheen. According to Sheen, his biggest bet ever was on the boxing bout between Manny Pacquiao and Oscar De La Hoya. He put a whopping $1 million into Pacquiao and won. Sheen told the NYT, “I had a dream a week before that he was going to beat De La Hoya like a drum, and he did. It was like, pfffft, whatever. I felt nothing.”
Gladys Knight, the Empress of Soul, has had a long stint with gambling. The show-stopper event was when she first won $60 thousand on blackjack and burned the winnings. Then she immediately shifted to a baccarat table and won $45 thousand.
For Gladys, the gambling addiction set in slowly and she began to look at the casino as a kind of safe space. She wrote in her autobiography that she felt protected behind red velvet ropes that kept autograph seekers, thieves, and scam artists at bay. The casinos brought food and drinks to her table, at no charge. Gladys was one of the few gambling celebrities who sought professional help and overcame her addiction. The driving force was that she was neglecting her duties as a mother.
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