High Rollers: Celebrities Known for Their Casino Adventures

Casinos, facilities for high-end gambling, are usually frequented by diverse individuals, especially the wealthy and middle class. From movie stars, musicians, to athletes, you find people from all walks of life. Lots of celebrities are regulars at casinos. Judging from their net worth, you know they are all in at the gambling tables. This brings Kenny Rogers’ evergreen song “The Gambler” to mind.

Many celebrities enjoy gambling and have made quite a reputation in this industry which is valued at $44 billion. Read on and let’s find out about them.

3 Famous Hollywood Celebrities Gambling at The Casino

The casino industry is very enchanting. This charm has commanded the attention of many famous personalities and Hollywood stars. The games available at slotozilla.com/ca/, like poker, blackjack, and more, are fascinating and have kindled the interest and intrigue of these stars.

1. Ben Affleck

Ben Affleck

  • Oscar-winning actor and director
  • Famous for playing several roles, including Batman
  • Skilled Poker and Blackjack player

When discussing famous gambling enthusiasts, Ben Affleck is always mentioned. This renowned Hollywood actor is no stranger to the excitement of the casino. Affleck’s game of choice is blackjack, and he is often seen at various casinos. Given his quick thinking and strategic approach, Affleck has earned the nickname “card shark” within the gambling industry.

2. Tobey Maguire

Tobey Maguire

  • Famous for playing Spider-Man in the Sami Rami’s trilogy
  • High-stakes poker player

Actor Tobey Maguire, famous for portraying Spider-Man, indulges in high-stakes poker as a beloved hobby. Media outlets highlighted Maguire’s participation in secret poker games alongside other notable figures and affluent players.

3. Charlie Sheen

Charlie Sheen

When you make a list like this one, you can’t skip on Charlie Sheen. It is just not possible. The man leads a crazy life and gambling is only a part of it. He was a part of a criminal betting ring and won big on boxing matches, but that’s only part of it.

When it comes to gambling, the Platoon actor is a big fan of sports betting.  If you didn’t know one of the primary reasons why Denise Richards got divorced from him is because he’s been betting $200,000 each week. Now, that’s quite a number. One of the biggest wins Sheen ever got was a million-dollar bet on a boxing match. 

He put $1 million on Manny Pacquiao to beat Oscar De La Hoya. The funny part is that he put this bet based on his dream where he envisioned a win by Manny. He won, but as Charlie later recalled it felt nothing special. Unfortunately, the Two and a Half Men actor was on the other side of betting too.

At one point in 2011 you could bet on his next misstep. Bookies offered odds on his next arrest and admission to a mental institution. Today, Sheen claims that the gambling adventures are behind him and that he is a retired gambler. However, suspect that his gambling activities will resume once he has another dream that will predict the next boxing match’s outcome. 

2 Music Artists with a Passion for Gambling

Hollywood actors frequently steal the show regarding gambling but don’t overlook the music industry. Celebrity gamblers in the music business come from various musical genres, and their passion for gambling is just as varied as their tastes in music.

1. Frank Sinatra

Frank Sinatra

Frank Sinatra was one American singer and actor considered the greatest American pop singer of the 20th century. He was one of Las Vegas’ elite gamblers, so much so that he owned 9% of a casino.

Sinatra’s prowess extended beyond the musical stage to the casino floor. Honing his craft, he often indulged in games of chance, making it safe to conclude that he was good at what he did both in music and at the table.

2. Sean John Combs

Sean John Combs

Combs, also recognized as P. Diddy, is a renowned American rapper and record producer who is a big influencer in gambling. Coupled with his feats in the music industry, Combs is an avid blackjack enthusiast.

He is often regarded as a game representative and has visited many casinos during his tours, where he has played at notable blackjack tables. According to sources close to him, Combs is a blackjack master.

2 Well-Known Sports Figures Involved in Gambling

The sports and gambling industry have long been interconnected for a while. Numerous professional athletes seek entertainment through casino games and sports betting. Several athletes have become famous for their fondness for gambling and knowledge in sports betting.

1. Michael Jordan

Michael Jordan, the famous basketball player known for his iconic slam dunks and championship victories, is also famed for gambling. He is called basketball’s most renowned bettor, and his gambling tendencies have been discussed for years.

Jordan’s fascination can be seen in his wagers on golf matches and high-stakes card games. While he has occasionally made headlines for his gambling habits, his legendary athletic legacy isn’t overshadowed.

2. Floyd Mayweather Jr

The former light-weight professional boxer has written his name as a sports hall of famer and is known for his extravagant bets. His deep love for sports betting is not a secret – he is very passionate about it.

He has gained quite a reputation for his daring and extravagant gambling adventures. Mayweather enjoys placing bets worth millions of dollars on sporting events and frequently posts about his winnings on social media.

Notable Mentions

George Clooney Clooney, a notable Hollywood figure, is a well-known gambler. He has gained attention for his love of casino games. He once co-owned a Las Vegas casino resort, the Las Ramblas Resort. Though the resort closed, his appreciation for the gambling world did not
Aubrey “Drake” Graham Ever heard of the “Drake curse“? This Canadian rapper, known for his musical talent, is famed for his gambling love. He gambles so much that he loses enough to bankrupt the average Canadian.  This, however, doesn’t deter him from gambling again
Pamela Anderson Another notable mention is Pamela Anderson, known for her “Baywatch” role.  She has become famous for gambling and once made a round in the news after losing $250,000 in a poker game. Not so much of a high-stakes player, she finds joy in vibrant slot machine collections

Final Thoughts

Gambling isn’t just a pastime for regular folks; celebrities are into it too! These famous figures have a genuine fascination and love for gambling, whether it’s playing card games, trying their luck at slot machines, or placing sports bets.

Now, while some celebrities have faced their fair share of controversies and the potential consequences, others prefer to keep their love for gambling on the down-low. But guess what? The casino is an industry that brings people together, irrespective of their fame or status.

Posted by
Natasa Pantelic

My name is Natasa Pantelic, and I work as a content editor for thetvjunkies.com. By profession, I am a business administrator and a professional makeup artist. I enjoy taking care of my appearance and health through strength training, cardio, and a healthy diet. I also have a passion for music, socializing, adventures, and embracing new challenges.