In recent years there’s no doubt that gambling has increasingly become part of the mainstream. A lot of this has to do with the explosion of the online casino sector which has introduced many more people to the excitement of games like slots, roulette, and poker.
But there’s one group who seems to have always been drawn to the glamor and thrills of gambling – celebrities. Ever since the 50s and 60s in Las Vegas which attracted celebrities like Frank Sinatra and Dean Martin, there have been countless others who have loved a bet.
This present generation is no different – as these seven individuals prove all too well.
Michael Phelps
Swimmer Michael Phelps may hold the esteemed title of the most successful Olympian of all time, but when it comes to gambling, he is far from being a fish out of water. His chosen game is poker, and he is notorious for his marathon sessions in casinos across the world. He first discovered an aptitude for the game by playing online and, since then, he’s gone on from strength to strength. He’s a high-stakes player who believes in putting everything on the line – probably the secret behind his Olympics success too.
Tobey Maguire
Not content with just being Spiderman in the blockbusting movies, Maguire has shown his commitment to also making a big impression in the poker world. Beginning his poker career back in 2004, he’s chosen to learn from the best with guidance from the legendary Daniel Negreanu, holder of no less than six prestigious World Series of Poker bracelets. Maguire has competed in numerous WSOP events, even winning a Hollywood Park Casino tournament with a first prize of $300,000. He was also rumored to be one of the real-life participants in the poker parties that were featured in the movie Molly’s Game starring Jessica Chastain.
Ben Affleck
Close friend of Maguire, and fellow superhero actor, Ben Affleck was also thought to be one of the Molly Bloom Circle of players. But perhaps his greatest gambling notoriety comes from his exploits at blackjack that has earned him a lifetime ban from the Las Vegas Hard Rock casino. This is where he was allegedly found to be using card counting to tip the odds in his favor – not illegal in itself but very much frowned upon by casinos. He’s had more luck with poker over the years, on one occasion winning $356,000 in a tournament.
Matt Damon
The third wheel in this sort of modern-day gambling Rat Pack is Matt Damon. As the star of the Ocean’s film franchise, it seems only logical that he would be a regular denizen of the real Las Vegas.
Poker’s his game and word around the tables is that he owes his success to the generally careful and cautious approach that he takes to the game. He also tends to maintain a lower profile than Maguire and Affleck, very much keeping details of his winnings to himself.
Pamela Anderson
The former Baywatch star has had a decidedly up and down experience when playing poker for money. One of her less fortunate experiences came when she took on Antonio Esfandiari in 2007, reportedly dropping $250,000 in the process. But she enjoyed better luck when she played against Rick Saloman. She may have lost the game to him as well, but at least she ended up with a proposal of marriage – one that she was happy to accept.
Jennifer Tilley
American Canadian actress Jennifer Tilley’s career has seen her receive an Academy Award nomination for her performance in Bullets Over Broadway, appearing in The Simpsons, and even being a judge on Ru Paul’s Drag Race. In the meantime, she has also carved out a very successful career for herself on the professional poker circuit. A holder of a prestigious WSOP bracelet for winning the 2005 Ladies’ No Limit Texas Hold’em event she’s also a regular on TV pro-celebrity poker shows. It’s estimated that her all-time winnings to date could be well over $1 million – and it’s also earned her the poker room nickname of J Tilla the Killa for her ruthless approach to the game.
Michael Jordan
The ex-Chicago Bulls guard, and a player well in the GOAT category in pro basketball, is as notorious for his gambling as he is for his sporting prowess. Even when in college he was placing bets on himself to win at pool and Magic Johnson was a regular cards-partner for the big man.
There’s also the famous story that one day he visited one of Chris Paul’s famous summer camps when he accepted a challenge from Paul to score three baskets in a row. If he failed, he would have to buy Air Jordans for everyone on the camp – he didn’t miss a single shot.
Of course, there are plenty more celebrities from all kinds of fields who enjoy a wager – but few are quite as notable as these!
