Betting Specials

Celebrity Gamblers: Famous Figures Who Love the Casino

Celebs and gambling go hand in hand; whether it’s blackjack, poker or roulette, the rich and famous flock to the casino. Find out who’s who in the celebrity gambling world.

​​There’s a link between brilliant actors and gambling. Considering that many actors use the all-in method acting style to get into character, it’s little wonder that some famous names become professional gamblers. Celebrities love spending money on their hobbies, which include fast cars, luxury lifestyles and, of course, gambling. 

Stars love to play the roulette table and use their acting skills to develop a compelling poker face. Several well-known names have mastered professional gambling skills which go way beyond a hobby.

Whether an amateur or professional, they all have one thing in common: an all-in attitude to everything they do, gambling, drinking, not to mention a fascination with love and marriage. 

However, it’s not just film stars who love a flutter; it’s sports people and celebs, too. Who would be a celebrity? All that fun and money. It’s a hard life! Here is a list of top celebrities who live life in the fast lane, starting with the original James Bond, Sean Connery.

Sean Connery Who Never Said Never Again

Everyone knows the Scottish actor Sir Sean Connery (now deceased) as the first person to play Ian Fleming’s fictional character James Bond, Agent 007. Connery set the bar high for those actors who followed in the role, creating the persona of a worldly jet-setting spy who enjoys playing high-stakes baccarat and roulette.

But what many cinema fans may not realise is that Connery was an accomplished gambler in real life. In 1963, he played roulette at the Casino de la Vallee in Italy, betting and winning on the number seventeen for three consecutive spins at massive odds of 37-to-1. Our real-life James Bond left the casino $27,000 more prosperous – a great day’s work if you can get it.

Charlie Sheen is ‘Two and a Half Men’

From a young age, Charlie Sheen, son of Martin Sheen, has had a comprehensive addiction to fame and an unhealthy attitude to gambling. The leading actor in the films’ Wall Street’ and ‘Platoon’ is known for his acting skills and perfect timing. 

In 2003, Sheen was cast as Charlie Harper in the sitcom ‘Two and a Half Men’. For that series, Sheen earned about $1.8 million per episode. So, Sheen has more than enough money to spend at any luxurious casino if he wants to; after all, it’s his money to spend.

In 2011, according to his ex-wife Denise Richards, Charlie spent about $20,000 weekly on sports betting alone. Celebrity commentators say that nearly all his gambling losses were through sports betting.

Ben Affleck Loves Poker

Ben Affleck is an award-winning actor, screenwriter and director. Despite his success in the movie industry, Affleck entered rehab in 2001 to deal with his addiction to gambling and alcohol, and he is open about regularly attending AA and GA meetings. 

Media pundits say the star loves playing online poker and blackjack (or he used to) and was so good that he won the 2014 California State Poker Championship. Affleck says that blackjack is his favourite game. So much so that some Las Vegas casinos banned him and his buddies because they broke the bank several times; winning like that sounds like he had the casinos running scared.

Affleck may have had a turbulent personal life, but he was honoured with the award for Best Original Screenplay in the movie ‘Good Will Hunting’ in 1998. In 2013, Affleck won an Academy Award for the film ‘Argo’ in the Best Picture category. More recently, his personal and on-screen life has become less bad boy-orientated and more settled, if his recent marriage to ‘Jenny from the Block’ and the long-awaited release of Hypnotic is anything to go by.

Matt Damon is a Bourne Poker Player

Playing the lead as Jason Bourne in ‘The Bourne Identity’ and five other Bourne blockbusters, Damon is another celebrity who loves gambling and, what’s more, he loves to do it with his friends, Afflick and Maguire – but more on that later.

In 2011, Matt Damon and Tobey Maguire participated in illegal gambling in 5-star hotels across America. Damon is a Texas Hold ’em poker fan and often plays poker with Tobey Maguire, Leonardo DiCaprio and Ben Affleck – known as the modern-day Rat Pack.

Tobey Maguire has Spider Instincts 

Maguire, the star of the Spiderman films, is a serious pro poker player. In 2011, Maguire was unsuccessfully sued for being part of an illegal gambling ring with his Rat Pack friends. 

The celebrity learned his poker skills from Canadian Daniel Negreanu, a professional poker player who won the World Series of Poker six times. Our sources say he is good at Texas Hold ’em, and it’s believed he has won over 10 million dollars in poker tournaments. 

Sadly, Maguire’s addiction to alcohol and gambling goes way back to when he was a teenager at just 19.

Tony Bennet at the WinStar World Casino and Resort

Tony Bennet is one of the celebrities who have performed at the WinStar World Casino. The 3,500-seat casino event hall has hosted some popular entertainment attractions, including Adam Lambert, Jay Leno, Vince Gill, Weezer, Kid Rock, Lil Wayne, ZZ Top, and Maroon 5.

There’s no official information on the gambling habits of these superstars, but the chances are they have spun the dice at the largest American tribal-owned casino. Should the celebs want an online flutter, we are sure they would study this VIP Casino Guide for Indian Players: to get the most up-to-date information. Tony Bennet has recently passed away, but his legend lives on. 

Tiger Woods Loves The Atlantis Bahamas

Woods is not an actor but a professional sportsman. Tiger Woods is one of the most famous and successful golfers ever and one of the most controversial. No stranger to headline gossip, Woods loves life in the ultra-fast lane, from divorce to the devastating car crash in February 2022. Wood’s rollercoaster life has been all over the news. 

With a net worth of over $1.1 b, it should be no surprise that Woods loves to gamble and has been seen hanging out at Wynn Las Vegas Encore Resort and The Atlantis Bahamas. Woods isn’t the only sportsperson who likes to bet.

Lex Veldhuis MMA and Poker Pro

Veldhuis, a famous MMA fighter, became well-known after a staged bout in Marbella with Bertrand “ElkY” Grospellier. Admittedly, this was some time ago, over 13 years ago, but it proves you can go from celebrity MMA fighter to professional poker player and keep your head.

Veldhuis is part of Pokerstars’ Pro Team and is an online broadcaster for major poker events. 

Lex Veldhuis won $62,620 at the PokerStars SCOOP Main Event in 2020 and placed 15th overall in the competition. He is a celebrity in the poker world and a star, all but briefly, in mixed martial arts. 

Floyd Mayweather Jr is a TKO

MMA fighter he is not, but Mayweather Jr is a veteran fighter in the boxing and MMA world, famously taking on Conor McGregor in the 2017 ‘Money Fight’ – defeating McGregor by a 10th round TKO (technical knockout).

Floyd Mayweather Jr. has quite a reputation for being a prolific gambler who enjoys betting on athletic events. He attempted to place a wager on his ‘Money Fight’. Gambling on himself when facing Conor McGregor. A battle in which he won $275 million. A $400,000 bet on himself was to win in under nine rounds, while another wager was to win via knockout.

Local bookmakers rejected Floyd’s wagers, and as he won in round 10, he would have lost the first wager anyway. It’s well-reported that Mayweather Jr enjoys sports betting on boxing and basketball matches. After wagering $350,000 on a double bet of a boxing match between Willy Monroe and Gennady Golovkin and a basketball match, he won a massive total of $827,273. The win confirmed what we already knew – he’s a success in and out of the ring.

So far, it’s been a man-heavy story, so to add some feminine charm, let’s talk about Jennifer Tilly.

Jennifer Tilly, AKA Bonnie Family Guy

Anyone who has ever watched poker on late-night TV  will know this Canadian-American actress and her love of the tables. Tilly is famous for voicing Bonnie from The Family Guy and is still acting, but her love for poker has made her even more well-known.

Tilly is a WSOP bracelet winner, having conquered the 2005 Ladies’ No Limit Texas Hold ’em event. She’s no fool, making her mark at various WPT events, the Celebrity Poker Showdown, and the Game Show Network’s Poker Royale – her live tournament winnings exceeded $1 million. Proving Tilly is a talented poker player who could take on the boys and win.

Gladys Knight, but No Pips

The singer’s famous catalogue includes chart-toppers like ‘Baby Don’t Change Your Mind’ and ‘Midnight Train To Georgia’ she freely admits she was more interested in blackjack than singing at one time. She famously warned her fellow church congregation that blackjack took priority over her life.

Knight reportedly said, ‘While some can control their habits, I couldn’t’ and thanked her fans, Gamblers Anonymous, the church and her family for getting her back on track.

Famous Fictional Gamblers Who Love the Casino

Danny Ocean in the Ocean series of films. One of the most famous film series centred around a casino. The suave and sophisticated George Clooney leaves us with no doubt that he’s a mastermind in the films but takes time to enjoy casino life nonetheless.

The filmmaker doesn’t tell us about the intricacies of gambling, but Ocean’s series of films is very entertaining. Celebrity lifestyles may be desirable, but they are also costly and not in the way you imagine.