Top 10 Most Famous Celebrity Gamblers
October 2, 2017
With their high disposable income, and love of the bright lights and the glamour, it’s little wonder that celebrities are often seen hanging around casinos on the Las Vegas strip and around the world.
Poker is surely the top choice for the celebrity gambler, but the likes of craps, blackjack, baccarat, roulette, and of course the sports book are all regularly frequented by the celebrity casino lover.
Some players are more passionate than others, but all our players on the list don’t hide their love for the game:
Undoubtedly the most famous golfer of all time, Tiger Woods was the face of the sport for many a year, and though he hasn’t won a major trophy since 2008, his career earnings are estimated to be over $1.4bn.
With so much disposable income to play with, Woods is well known for playing on the blackjack high roller tables in Las Vegas where he has a million-dollar betting limit, and often plays $25k hands.
“Tiger is excellent at blackjack. He bears down a little bit, pays attention, and plays perfect basic strategy. He takes his losing hands well and doesn’t get upset, though you do see that extra bit of focus at times,” said famed poker professional Phil Hellmuth.
Matt Damon is one of the highest grossing Hollywood actors of all time, has won an Academy Award for his screenplay Good Will Hunting, and is estimated to be worth $160m.
Damon played a leading role in the poker-based film ‘Rounders’ in 1998, and transferred that poker experience into real life, appearing at the World Series of Poker in 2009 and 2012.
“I lasted six and a half hours. I had a bad beat, because I had Kings and this guy, who is the best poker player in the world, beat me with two Aces,” said Damon on his WSOP experience. “But it was great, because I knew I would lose eventually, it was just a good story to leave it with.”
Aside from Eminem, 50 Cent is arguably the most famous rapper of the 21st century, has sold over 30 million albums worldwide, and has starred in a number of films and TV shows.
50 Cent loves nothing more than a flutter and bets huge amounts regularly on the sports book, and in the past, has wagered over $1m on one bet, predicting Floyd Mayweather to beat Manny Pacquiao in 2015.
“Champ is going to do it. He’s going to smoke him. It’s going to look like he pumped up for no reason,” said Jackson, before replying to a question on how much he’d wager, “Probably like 1.6 [million]. I’ve been thinking this out. I’m going to make a real bet.”
The greatest boxer of all time, Floyd Mayweather is the only professional boxer to fight fifty times without losing a single bout. Never ducking a big fight, Mayweather earned nearly $1bn throughout his 21-year professional boxing career. It’s little wonder he nicknamed himself ‘Money Mayweather’ in 2007.
Floyd is often seen flashing the cash on the slot machines in the casinos of Las Vegas and on the sportsbook where he attempted to put $400,000 on himself beating Connor McGregor in under 9.5 rounds.
“I think that we bet 100 on 9.5,” Mayweather said after his 10th round victory. “I gave my guy six figures to go bet. I have to make sure he bet because earlier today I went to the sports book to bet and they wouldn’t let me bet.”
Charlie Sheen is one of the most famous actors in the world, and despite starring in Two and a Half Men, Platoon, and Young Guns, Sheen is probably most well-known for his eccentric and mind-blowing lifestyle.
To go along with all his partying, Sheen was commonly seen at the sports book during the mid-2000’s, and was also a stalwart of the Las Vegas casinos. In 2008 he put $1m on Manny Pacquiao beating Oscar De La Hoya in a boxing match.
“It was a wrong-way spread and I had a dream a week before that [Manny] was going to beat De La Hoya like a drum, and he did,” said Sheen at the time.
One of the most legendary names in the sporting arena, Ronaldo twice won the coveted world footballer of the year, and is considered by many to be one of the best strikers in the history of the sport.
Since retiring, Ronaldo became a member of PokerStars in 2013, and later that year battled tennis star Rafael Nadal in a charity event. Ronaldo made his first entrance on the poker tour in 2015 picking up over $40,000 in the process, and also appeared on the poker TV show Shark Cage in the same year.
“I really don’t play football anymore, even with friends, but when I play poker, I’m very competitive. Every time I play, I want to go far. I want to win. I always look to give my best in everything, in football and in life. Poker is another challenge that excites me,” Ronaldo said upon joining PokerStars in 2013.
Ashton Kutcher is the Hollywood heartthrob of a generation, and has catapulted into becoming one of the most recognisable actors on the planet since the turn of the century. Kutcher, who’s an avid sports fan, is the star of Two and a Half Men, Just Married, The Butterfly Effect, and is also married to Mila Kunis.
In 2013, Kutcher revealed that he headed the ‘largest national sports-betting syndicate in America’ which pinpointed anomalies in college football matches, and as a result took advantage of the chinks to win big money.
“We were clearing, like, $750,000 in four weeks of college football. It was pretty fun. Then they [sportsbooks] caught on. The hypothesis had been that the house would just assume that I was a dumb actor with a lot of money who liked football,” said Kutcher.
Without doubt the most famous basketball player of all time, and potentially the most famous sports star on the planet, Michael Jordan transcended sports and was the face of the Nike brand through the late 80’s and 90’s, and is the richest person in sports history.
As far back as 1992, Jordan was routinely spotted playing poker till the early hours, and would later make worldwide headlines after suffering some big losses on craps and golf betting.
“I apologize to Michael for saying this,” said former teammate Charles Barkley in 2017. “We’d be playing golf with certain people, and we’d be playing a couple of hundred dollars a hole. But he’d be playing some for guy for $100,000.”
Pamela Anderson has one of the most recognisable faces in the world. The former Baywatch star has been a regular on the silver and big screen since her breakthrough in 1990, and has modelled for Playboy for over 20 years.
Anderson, who was married to professional poker player Rick Salomon on two separate occasions, founded the website PamelaPoker.com in 2006, and is a regular visitor to Las Vegas, though her poker ability is questionable. Anderson once lost $250,000 to Antonio Esfandiari in one poker session.
“I was playing poker one night and I was down about 250 grand. He said if I made out with him, that he would clear the [bet]. I paid off a poker debt with sexual favours and I fell in love. It’s so romantic,” said Anderson in 2007.
Michael Phelps is the most successful Olympian of all time, and throughout his glittering career won 23 Olympic gold medals and set 39 world records during 16 years of competing in the pool.
Phelps started to play poker intermittently just before his record-breaking Olympics in 2008, but since retiring from swimming, Phelps has started to take the game more seriously and has placed in six ranking tournaments.
“I’m just learning more from what these guys do on a day-to-day basis and trying to just figure different things out. It’s always fun. It’s a challenge, but it’s entertaining for me. It’s something I’ve always liked, and my wife [Nicole Johnson] plays as well, so it’s in the family,” said Phelps.
So many more celebrities across the globe love a flutter every now and again from all sorts of backgrounds. As you can see from our article on sports players who’ve turned to poker.
‘America’s pastime’ is a huge hit, but blackjack, roulette and the sportsbook all feature heavily for the celebrity gamer too. To have a read of how these games work, and how to play them, give our guides and tips a read here.
Author: Tom M.
Tom has been creating online content for over 10 years now starting way back as a small, impressionable 16-year-old. Tom mainly writes about sport and gambling, but every now and then also delves into fleshier subjects like politics and psychology. When he was 18 he created HungarianFootball.com and over the last few years he's written on a freelance basis for ESPN, WorldSoccer, Goal.com, among many others.