10 Celebrity Superstars Who Love Gambling

Author: Jack Meyer

When we imagine people in casinos, it’s not often that we think of celebrities gambling and taking part in this pastime. Yet you may be surprised to know that there is a good number of stars from the worlds of film, music and sport who enjoy gambling of one kind or another. Here, we’re going to take a look at the top 10 celebrities who love gambling.

Michael Jordan

Michael Jordan is well-known as a former basketball player in the NBA. He helped to raise the popularity level of basketball in the 80s and 90s. So much so that he ended up starring in the 1996 film Space Jam alongside Bugs Bunny and other toons. Yet he’s also known for the odd gambling splurge as well.

According to a 1993 book by San Diego businessman Richard Esquinas, he and Jordan faced one another on the golf course once. The pair bet against one another at golf on frequent occasions, with the author highlighting $100,000 putts, swinging upwards to a quarter-of-a-million dollars. One time, Jordan ended up losing $1.25 million to Esquinas through golfing.

Pamela Anderson

In the 1990s, Pamela Anderson was the woman that every man wanted to be with and every woman wanted to look like. Known for portraying C.J. on the television series Baywatch and for her nude Playboy magazine shoots, Anderson achieved quick fame and fortune before controversy surrounded her thanks to a leaked sex tape with former husband and Mötley Crüe drummer Tommy Lee. Yet she has also been linked to gambling in more ways than one.

In October of 2007, Anderson married American nosebleed-stakes poker player Rick Salomon. They separated in December of the same year, and the marriage was annulled in February 2008. Some say that she only married him initially because she lost a bet with him. Yet the former glamour model is also a fan of live roulette and loves visiting the opulent land-based casinos in Las Vegas.

Matt Damon

A big Hollywood actor, Matt Damon is frequently ranked amongst the Forbes list of the most bankable stars. Starting out his acting career in the 1988 film entitled Mystic Pizza, it was in 1997 that he and Ben Affleck (another avid gambler to come later) wrote and starred in Good Will Hunting. Both received an Academy Award and Golden Globe for Best Screenplay, which helped catapult them into the mainstream.

Damon has also starred in a film about gambling – 1998’s Rounders. Of course, the actor would be more than capable of portraying a gambler, considering he enjoys the activity in real life, too. While preparing for his role in that film, he was coached by a professional poker player. It was this that made him fall in love with the game, and he has continued gambling ever since. Damon’s first love is blackjack, but he will likely always have an affinity for poker, too.

Tiger Woods

Professional golf is the game that Tiger Woods is known for, having tied for first in PGA Tour wins, being second in men’s major championships and has achieved multiple other golf accolades. An inductee into the World Golf Hall of Fame in 2021, he suffered through a National Enquirer article revealing his infidelity over 10 years prior. He has also been part of several car crashes and a 2017 arrest for driving under the influence of alcohol or drugs.

His personal life has, without a doubt, been problematic. Yet he has at least managed to focus his mind on something else at times – gambling. Woods is a passionate gambler, having a love for blackjack more than anything else. Reports suggest that he has gambled and won vast sums on the game throughout the years. Tiger used to frequent a variety of Las Vegas casinos at one time, although has reduced his visits of late.

Tobey Maguire

If you’ve seen the Spider-Man trilogy of films from Sam Raimi (2002 – 2007), then you’ll know Tobey Maguire as the actor portraying the central character. The Californian star has taken up roles in various other films along the way, too, such as Fear and Loathing in Las Vegas, Pleasantville, Wonder Boys and The Great Gatsby, to name a few. Yet acting isn’t the only activity he is good at because Maguire is also a whizz at the poker table, too.

He began playing at a professional level in 2004, being tutored by one of the best in the industry – Daniel Negreanu. He has participated in the World Series of Poker Main Event on multiple occasions. Maguire also won the Hollywood Park Casino tournament, securing a nice payout of $300,000 from it. Often times you can find Maguire gambling alongside his celebrity friends.

Jennifer Tilly

Speaking of actors who enjoy playing poker, Jennifer Tilly holds such a status. The actress, who has starred in films like Child’s Play, Made in America, Music from Another Room, and Tideland, clearly gets her gambling prowess from her father. He was a poker player, too and provided her with the video game World Series of Poker. Upon moving to Hollywood, she was taught how to play the real game by her boyfriend.

Tilly would go on to win a WSOP bracelet in 2005, securing a payout of $158,625 in the Ladies’ No-Limit Texas Hold’em event. For that, she beat out 600 other players. Jennifer has partaken in the Poker After Dark show as well. At one point in 2005, she spoke of pursuing poker as a professional career instead of acting, and who knows, she might have become one of the most famous gamblers in that alternate scenario. Yet by 2008, she announced her retirement from poker as a career option. Two years later, she was back at it, and as of 2019, her earnings from the game exceeded $1 million.

Curtis "50 Cent" Jackson

Most people know 50 Cent as a rapper and occasional actor. Discovered by Eminem in 2002, he signed to Shady Records and then released his first album in 2003 – Get Rich or Die Tryin’. It was a huge commercial success, spawning hits like “In da Club” and “21 Questions”. Several albums since then have been released, and he entered into the acting world with his debut in a film named after his first album.

His forays in the gambling world have also been well-documented. In 2012, 50 Cent won $1 million on a bet after wagering on hometown NFL team New York Giants in Super Bowl XLVI. They went on to beat the New England Patriots, securing the rapper his big payout. One year prior to this, he won big after a $500,000 wager on the Giants beating the San Francisco 49ers in the NFC Championship Game.

Brad Pitt

Whatever your thoughts on Brad Pitt, there is little doubt that he is one of the best actors alive today. He has the awards to prove it too, having achieved two Academy Awards, two British Academy Film Awards, two Golden Globe Awards, and a Primetime Emmy Award. He has also been cited as one of the most powerful and influential people in the American entertainment industry. Doubtless, he also gained recognition as the husband of Jennifer Aniston and then, later on, Angelina Jolie.

Pitt isn’t like many other gamblers on this list, though. Brad Pitt prefers gambling on slots. While he was filming the hit Ocean’s Eleven movie in 2001, he acquired his taste for the machines. After the shooting of the film was over, his love of these games remained. He has often been seen in the casinos of Las Vegas, fulfilling his enjoyment for them.

Ray Romano

American stand-up comedian and actor Ray Romano is best known for appearing as the titular character in the sitcom Everybody Loves Raymond. He received an Emmy Award for his appearance in the show. While he has also ventured into various films, Romano has placed a lot more focus on TV series. This includes roles in The King of Queens, The Knights of Prosperity, Parenthood and Get Shorty.

He's also been spotted numerous times on the celebrity poker circuit. He remains one of the most active gamblers in Hollywood, being frequently pictured in Vegas playing poker. Romano has even participated in the World Series of Poker on more than one occasion. He does have a penchant for poker more so than anything else, although has engaged in one or two other casino games, too.

Ben Affleck

You can’t create a list of celebrity gamblers without mentioning Ben Affleck. Alongside his acting career, many stories have been published about Affleck's penchant for gambling. So much so that a few years ago, reports suggested he had been banned from the Hard Rock Casino due to winning so much on blackjack games via card counting strategies. He is regularly spotted in multiple Las Vegas venues but is also known to visit a live casino or two on the web.

Affleck is known for placing massive bets and has experienced both big successes and large losses. His biggest loss came about in 2001 when he said goodbye to $400,000 on a single hand of poker. Yet in 2004, he won a vast $356,000 while participating in a poker tournament. The aforementioned Tobey Maguire was one of his opponents at the time. Without a doubt, he is the biggest celebrity gambler in the world right now.

Final Thoughts

In conclusion, the world of gambling is not limited to ordinary individuals. Celebrities from the realms of film, music, and sports also find themselves drawn to the thrill of placing bets.

These celebrities not only captivate audiences with their talents but also showcase their love for gambling, reminding us that even the most successful and celebrated individuals find excitement and enjoyment in games of chance.