Rich and Glamour: Top Celebrities Who Are No Strangers to Gambling

Gambling is a wild experience for most of us, and good reasons! It’s thrilling, nerve-racking, and inherently popular. So, it is no surprise that many high-rollers in the casino industry have strong ties with the word “celebrity.” And yes, we’re talking about celebrities who are no strangers to casino fever.

In this article, we will list top celebrities who are avid gamblers from traditional settings to online casino platforms. Read more below and check which of your favorite artists are secretly a high-roller behind the scenes.

Brad Pitt

We all know him; from Ocean’s 11 to titles such as The Curious Case of Benjamin Button, Brad Pitt has been a household name in Hollywood as one of the sought-after actors of the decade.

But not everyone knows he developed a love for gambling throughout his career.

It is said that it all started when he prepared for his titular role in Ocean’s 11, which piqued his interest in several casino games like poker, blackjack, and online tables like FanDuel slot games, for example.

Because of his presence in gambling, he undoubtedly pulled in more people playing online lotteries or slots. As of the latest news, he intends to play and take this hobby seriously.


Mr. Sean Combs, also known by his rapper P.Diddy, has been a familiar face in the paparazzi’s lenses in different casino establishments. With P.Diddy being an avid fan of the games, he even took the chance to inaugurate one of the blackjack table games in Atlantic City.

Additionally, there are talks where he would often request a blackjack table during his tours as entertainment, and he would even invite many people and staff on board for a few games in between concerts. Also, P.Diddy is one of the high rollers bettors who made headlines for placing a $250,000 bet against Mark Walhberg during the iconic Pacquiao-Mayweather Boxing fight.

Ben Affleck

The famous Batman actor Ben Affleck is not a stranger to the glitz and glamor of casinos. This actor has been seen on casino floors and tables in different states and countries. And that’s understandable, seeing that he is one of the wealthiest actors in the industry.

Ben Affleck is also placed in headlines for his astonishing wins and losses. In 2015, Ben Affleck knowingly lost $800,000 on a New England Patriots bet in that year’s Super Bowl.

Leonardo DiCaprio

Like the artists mentioned above, Leo has a taste for fine entertainment and big-money pleasures, just like any avid gambler with the money and confidence to match. The Academy Award actor is known to visit the top casinos in Las Vegas and various parts of the world.

Fun fact: DiCaprio is a known guest at some of the most expensive hotels like the NOBU Hotel and Caesars Palace Las Vegas Hotel and Casino.

Matt Damon

Long-time actor and Oscar nominee Matt Damon gained a strong vibe for gambling through his experience working in the 1998 movie “Rounders.” In the movie, Matt Damon plays a law student discovering the world of gambling to bail out a friend.

The movie portrays actual poker scenes and strategies as practiced by many professionals. As it should be, Matt himself is coached by Johnny Chan, a professional poker player for his role. After the movie flourished and work was done, Matt continued his newfound love and learned real-life poker and blackjack skills.

Tobey McGuire

Apart from being a titular character loved by many generations, Tobey McGuire has been in love with the gambling scene, especially poker and blackjack, since his teenage years. Most reports say he is skilled in most games, showing prowess in and out of the camera.

Although he had some controversies about his gambling, reportedly losing big bucks to Ben Affleck in 2004, McGuire still has the money and time to lounge around in casinos over the years.

Charlie Sheen

Charlie Sheen has been associated with controversies and scandals under his name at his peak. So it is unsurprising that he is also an avid gambler, but he may have second thoughts to play as wild as before.

According to his controversies, Sheen reportedly lost $1,000,000 on a Super Bowl wager supporting the Los Angeles Rams. Charlie Sheen also had some heavy losses in recent years, especially in most sportsbook games.

Paris Hilton

Charlie Sheen’s controversies topple down on what Paris Hilton’s career plunged into in the early and mid-2000s. The actress has been associated with many personal and legal issues, including gambling. Today, she still plays tables and other casino games regularly, earning both wins and losses under her name.

Final Thoughts

The artists above are just a handful of hundreds of celebrities dabbling with money either online or on-site casino platforms. Although it is an expensive hobby, remember that their earnings and losses fall short of experts playing in silence and anonymity. That said, actors and celebrities are only human, and it should not be a big surprise that they play, win and lose money as any other gambler.