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From Ben Affleck To Jennifer Tilly To Queen Elizabeth To Curtis “50 Cent” Jackson: Top 10 Celebrities Who Love Gambling

20 May 2021

Most people dreamed of being an A-list celebrity and living in the constant shine of that glamorous spotlight. These personalities live luxuriously: sleeping on ultra-lavish mansions, going on unique vacations on exotic beaches, and eating at 5-star restaurants.

However, unbeknownst to some, some famous people find comfort and leisure at a gaming table, specifically in high-end casinos. If you’re curious about who’s who, here are the top celebrities who love the thrill of gambling whilst not necessarily being the most successful gamblers in the world.



1. Ben Affleck

Benjamin Géza Affleck-Boldt, or Ben Affleck in short, has taken many characters throughout his acting career. One of his notable performances was his titular role as the crime-fighting blind hero, Daredevil. He also helmed another superhero role as Batman in different DC movies like Justice League and Batman vs. Superman.

During his downtime, he enjoys playing card games. Like an ordinary person, Ben Affleck had ups and downs in gambling. He is one of the brightest blackjack and poker players but was frequently presumed to be counting cards. In 2001, he battled a gambling addiction and was sent to rehab.

He also won the California State Poker in 2014 and took home $356,000. He also reputedly won $800,000 with Matt Damon but gave a $150,000 tip to the dealer. In addition, he won $1500 in less than twelve minutes.



2. Jennifer Tilly

Jennifer Tilly, born Jennifer Ellen Chan, is an American actress. Some people may know Jennifer Tilly in Jim Carey’s Liar Liar or Woody Allen's Bullets over Broadway. However, most of us remember her in the Child’s Play franchise, where she played Tiffany Valentine or Chucky’s bride. After that, she became an icon in the horror film niche.

She is also a semi-professional poker player. She was immersed in poker during her early years as her father was a poker player. The actress then learned the game correctly from her current boyfriend Phil Laak, an Irish-American professional poker player.

In 2005, she won a World Series of Poker bracelet during the Ladies' No-Limit Texas hold 'em event. In the same year, she rose to the top at the third World Poker Tour Ladies Invitational Tournament. Unfortunately, her poker career was cut during her 2008 retirement.

However, after two years, she went back into the game and has since earned close to a million dollars in poker games. Subsequently, she was nominated in 2014 for PokerListing's Spirit of Poker Living Legend Award.



3. Tobey Maguire

Third on the list is the third actor who played Spiderman on the television and the big screen, Tobey Maguire. Born as Tobias Vincent Maguire, Tobey is an American actor and a producer. Aside from the Spider-Man trilogy from 2002 to 2007, he has notable roles in Seabiscuit and The Great Gatsby.

In 2004, he dabbled with tournament poker and learned the game from a Canadian professional poker player, Daniel Negreanu. In the same year, he lost to Ben Affleck for an undisclosed amount of money. He quickly got it back from the Hollywood Park Casino tournament held the same year. The actor joined the 2005 and 2007 World Series of Poker Main Event Championship, where he garnered $51,669.

Maguire also joined American entrepreneur Molly Bloom’s high-stakes poker games during the mid-2000s. This stint gave bad publicity to him as he ordered Bloom "bark like a seal" after winning. Consequently, the event had inspired the movie Molly's Game, where his actions were portrayed by the character Player X.

Tobey also beat Bradley Ruderman, a celebrity investor, and got over $300,000. However, Ruderman accused him of cheating and sued him. Eventually, the court didn’t find the Spider-Man star guilty.



4. George Clooney

George Clooney is an American actor, screenwriter, film director, and producer. His fame rose when he played Danny Ocean in the Ocean’s trilogy from 2001 to 2007. Clooney was one of the most handsome bachelors in Hollywood before marrying Amal Alamuddin in 2014. Aside from being an A-list celebrity, he is a philanthropist and has a variety of advocacies.

Clooney is also a gambler. Since he was a child, he has been playing card games and was awakened during his role in Ocean’s 11. George Clooney also contributed to private Hollywood gambling games together with Tobey Maguire.

The actor also planned to open a casino called Las Ramblas. He put a considerable amount of money into the project, but it did not come to fruition.



5. Derren Brown

Other than celebrities, this list also includes famous people from different professions. Derren Brown is a London-born mentalist and illusionist. He became famous from his television show in 2000 called Derren Brown: Mind Control. Since then, he has made several shows on stage and television. His shows are meant to reveal the secret of those who claim that they have supernatural powers.

Like others on the list, he loves gambling, although it was only short-lived as he was a terrific gambler as told by SpinCasino. Some casinos have banned him due to his superb skills, and he only places small bets and never loses. Moreover, he uses his power of suggestion and ability to predict his opponent’s intentions when playing blackjack or poker.



6. Pamela Anderson

Anyone who doesn’t know or heard of Pamela Anderson has been living under a rock. She has been deemed a hot icon due to her photos in Playboy magazine and her role in Baywatch. The Canadian-American actress also involves herself in different causes like animal rights and AIDS.

Anderson loves playing poker, but there isn’t enough data to say that she’s good at playing it. She is currently married to her third husband, Rick Salomon, a poker player. There is a rumor surrounding her partnership speculating that she married him to settle casino debts. Anderson also appeared in the news when the bombshell lost $250,000.



7. Tiger Woods

Eldrick Tont Woods, a.k.a. Tiger Woods is an American golfer. Known as one of the famous golfers in the world, he holds numerous golf records and championship wins. Many people have watched him play and bet on him winning. Although Tiger cannot bet on himself, he still enjoys gambling when he’s off the golf course.

Leaving aside playing poker, Tiger Woods has held a poker tournament for almost two decades. It was dubbed the “Tiger Jam Tournament,” a charity event held in Las Vegas.



8. Allen Iverson

Allen Iverson is an American professional basketball player, playing from 1996 to 2011 as a shooting guard and point guard. During his career, he has worn different team jerseys but has played twice for the Philadelphia 76ers.

He has also been into gambling and had an addiction. His gambling style has led him to be banned from both Atlantic City and Detroit casinos as told by the Bleacher Report.



9. Queen Elizabeth

Next on the list is no other than her Royal Highness, Queen Elizabeth II. She is Duke and Duchess of York’s eldest child, later known as King George VI and Queen Elizabeth I.

The Queen was home-schooled, and the lessons primarily revolved around music, literature, history, and language. When the Second World War erupted, she assumed public duties under the Auxiliary Territorial Service as a mechanic and military truck driver.

As historians have written her history, the Queen is almost an open book. However, unknowing to all, the Monarch had her share of games of luck. She loves to gamble, especially with roulette, slots, and horse racing. She had garnered more than $8,000,000 by betting or entering the race through one of her horses.



10. 50 Cent (Curtis Jackson)

Last but not least is Curtis James Jackson III, or better known as 50 Cent. He is now in the music industry as an American rapper and songwriter. On top of that, 50 Cent is also an actor, television producer, and entrepreneur. He has been described as the authority in “nuanced art of lyrical brevity.”

Aside from his prolific career, he is also a knack for sports betting. During the match between Manny Pacquiao and Floyd Mayweather, Jr., he bet $2 million on the latter. Mayweather, Jr. won, and so 50 Cent. The rapper also had a $500,000 bet on the championship match between San Francisco 49ers and New York Giants.

As this article attests, gambling is not reserved for the masses. Celebrities also enjoy the thrill of playing poker, roulette, or any other games that include gambling. Gambling is an excellent way for anyone to have a good time. It doesn’t matter if you’re an office worker or an A-list celebrity, as long as you enjoy gambling.

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