Throughout the decades, big bucks have been spent in the gambling industry by many well-known celebrities. Gambling has been practiced among top celebrities for years, since the time of Mozart. Many top rollers in reputed international gambling sites are world-famous singers, actors, rappers, etc. In this article, check out the top celebrities in the gambling industry.


Top celebrity high rollers in the gambling industry

Many of the top high roller casino players worldwide are famous celebrities. They raise the stakes with millions of dollars. Wins and losses amounting to several million dollars are a regular part of their gambling experience. Fans like to stay updated on their gambling activities and the eye-brow-raising amount of money spent. The following are the top celebrity high rollers in the gambling industry.

  • Matt Damon
  • Drake
  • Ben Affleck
  • Brad Pitt
  • Jessica Simpson
  • George Clooney
  • Paris Hilton
  • 50 Cent
  • Snoop Dogg
  • Micheal Jordan

Matt Damon


The award-winning American actor and producer is known as one of the best high rollers in Hollywood. His interest in the casino industry can be traced back to 1998 when he acted in the movie Rounders. The movie required diving deep into the gambling space and understanding its quirks. He was coached by the world-class poker player Johny Chan for the role. Since then, he has been actively involved in gambling and frequently visited many of the world’s best casinos.


Reports show that the Canadian singer and rapper has spent over a billion dollars in a year alone on the casino site Stake, his top choice for gambling. His biggest loss happened in 2022 in Las Vegas, amounting to $275,000.

With the username DeepPockets6, he places massive bets on casinos and sports. He wagered $800 million worth of cryptocurrency on the crypto casino Stake within 2 months after joining the platform as a new player. The rapper does not hesitate to make his gambling activities public and delights his fans with news about his wins from time to time.

Ben Affleck


Like his close friend Matt Damon, Ben Affleck’s gambling journey kickstarted when he played the lead role in Runner Runner, a movie heavily based on online casinos. He is known for his love for blackjack and poker and is a high roller. Frequently visiting casinos worldwide, he is well-known for his generous tipping habits. Even though Runner Runner did not gain the success it expected, it paved the way for Ben Allefck to become a high roller.

Brad Pitt


The Ocean’s movies played a major role in getting Brad Pitt interested in gambling. Reportedly, many other celebrities were influenced by the same movie franchise. Brad Pitt is most into blackjack and poker, like Ben Affleck. It was necessary for the actor to visit and gamble in brick-and-mortar casinos to get into his role in the movies. While he is not actively involved in gambling like many other celebrities, he is a high roller who plays with big bucks when possible.

Jessica Simpson

The American singer and actress Jessica Simpson is known for her unusual gambling habits. She recently purchased a luxurious suite at the Palms Casino Resort, Vegas. The resort is known for being a hotspot among high rollers. By buying a suit there, Jessica aimed to be in the center of the action and gamble when the mood strikes.

George Clooney


As one of the Ocean’s franchise stars, George Clooney clearly understands and is interested in how casinos work. In fact, he attempted to buy a casino business in 2005, though it did not happen. Instead, he pursues his love for gambling by visiting the best casinos worldwide.

Paris Hilton

The American TV personality, model and actress Paris Hilton’s gambling activities are widely known. She is often spotted at casinos in Vegas, staking big money on various games.

50 Cent


The businessman and hip-hop arctic 50 Cent is more into sports betting than casino gaming. Throughout the years, he has lost a lot of money while gambling. However, he has also won a few million dollars along the way.

Snoop Dogg

The rapper Snoop Dogg does not find it enough only to become a high roller. He is actively involved in transforming the crypto-gambling industry through his partnership with the betting site Roobet. He has big plans to expand Roobet and provide new gambling experiences to its players. Snoop Dogg is already familiar with the cryptocurrency market and wants to bring its advantages more prominently in the online casino space.

Micheal Jordan

The legendary basketball player Micheal Jordan is known for his peculiar wagering habits. The gamble is not limited to a casino. He has been known to bet on anything from rock-paper-scissors to golf. The stakes he adds for each bet are massive, going up to several hundred thousand dollars.

The staggeringly large amount of money celebrities spend on gambling seems frivolous to some. For others, it is entertaining to learn more about it. With many celebrities actively involved in the casino space, fans are inspired to follow suit for big winnings.