Famous Celebrity Gamblers

Celebrity Gamblers: Top Actors Who Play at Casinos

8 min

Gambling has attracted celebrities; some became professionals, while some developed addictions. We compiled a list of celebrity gamblers who love to gamble.

Ben Affleck and his gambling superpowers that got him banned

Ben Affleck and his gambling superpowers that got him banned
Source: latimes.com

Affleck is an avid blackjack player, which leads him into trouble with the Hardrock casino owner.

He has been into gambling for most of his life and has a track record of winning at high-stakes poker tables.

Affleck’s route to becoming a famous gambling addict:

  • In 2001, Ben won $800,000 in blackjack by playing three $20,000 hands simultaneously in a single night.
  • Affleck won the 2004 California State Poker Championship earning $356,400 in cash and an opportunity to qualify for the World Poker Tour championship game in the same year.
  • The infamous incident in 2014 had all ears, as he was banned from playing blackjack at Hard Rock Cafe in Vegas after he was found counting cards following several wins, though not illegal but unpleasant to casino owners.

Many believed that gambling addiction was the cause of his career’s decline in the middle of the 2000s, but he has denied claims of being an addict.

Blackjack from Vegas migrated to online versions. In the UK, Blackjack casino sites allow you to play both the classic, virtual version or the live version with a real-time stream of a professional dealer.

Ben Affleck – worst reputation in the casino industry

A casino dealer uploaded a TikTok video criticising Affleck as one of the cheapest in the casino industry, along with plenty of anecdotes to shame him.

She depicts Affleck and his wife, Jennifer Lopez, as a nightmare couple due to their rude behaviour in the casinos.

Tobey Maguire: “With great power comes great responsibility”, even if it’s gambling

Tobey Maguire With great power comes great responsibilityeven if it's gambling
Source: pagesix.com

Tobey Maguire starred in Marvel’s Spiderman and was a controversial yet successful figure regarding his total winnings of $223645 in regulated high-stake poker games.

Maguire’s gambling highlights:

  • Maguire started playing poker in 2004, and soon became a skilled player, and won $95480 at the 2004 National Championship of Poker
  • Along with Ben Affleck and Leonardo DiCaprio, Tobey Maguire was one of several Hollywood celebrities who played in Molly Bloom’s high-stakes poker game during the mid-2000s
  • His big poker wins result from the training he received from poker professional Daniel Negreanu. Most tips are in Negreanu’s book, deemed one of the best Texas Hold Em books of all time.

Tobey Maguire gambling controversy

Tobey was among the individuals sued by trustees for allegedly winning $30,000 from Ruderman in a series of high-stakes Hollywood poker games, which he later settled for $80,000.

Matt Damon and how he was reeled into High Stake gambling by Hollywood

Matt Damon and how he was reeled into High Stake gambling by Hollywood
Source: cheatsheet.com

The actor behind movies like Good Will Hunting, and The Martian, doesn’t have a reputation as a celebrity gambler, even though he enjoyed a game of poker at private tables and competed in a series of World Poker tournaments.

Damon’s interest in Poker through time:

  • Inspired by his role in the 1998 movie Rounders, Damon was interested in playing high-stakes poker in the 2000s.
  • He has participated in several World Series of Poker (WSOP) tournaments, including the 2010 WSOP, but lost it to Canadian Jonathan Duhamel.
  • Unlike other Hollywood stars, Matt was never into celebrity gambling shows. However, he has participated in Texas Hold ’em games.
  • Though he loved to gamble, he was never obsessed with it and participated in the 2009 Ante Up for Africa charity event, a poker tournament that drew celebrities worldwide.

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Pamela Anderson and her intimate relationship with gambling

Pamela Anderson and her intimate relationship with gambling
Source: glamour.com

The Canadian American actress and model Pamela Anderson were one of the early female faces of celebrity gamblers during the late 1900s.

Notable gambling moments:

  • Despite not playing as frequently as other celebrity gamblers, she could be spotted wagering on blackjack, poker, slots, and baccarat, in Las Vegas casinos where A-lister celebrities flocked to gamble.
  • She caught the attention of the poker community when she lost $250,000 to her ex-husband Salomon in a single poker session.
  • She filed a divorce soon after her ex-husband Salomon won $2.8 million in the World Series of Poker Big One for One Drop tournament.
  • She was the ambassador of the online website BamPoker, by Canadian entrepreneurs back in 2012.

Slots are still the most popular games, both in Vegas and online through the specialised slot sites available.

Pamela paid poker 250 grand debt with sexual favours

Once Pamela revealed that her 250 grand debts from playing poker cleared when she made out with him and later, she fell in love with him.

Gambling addiction can creep up unknowingly at first, with gambling debt as one clear sign. We recommend you make a budget and stick to it!

Charlie Sheen and his million-dollar gambling win

Charlie Sheen and his million-dollar gambling win
Source: usatoday.com

Charlie Sheen, one of the highest-paid American television actors, is definitely not in the good books due to his long list of addictions.

From alcohol, drugs, and sex to gambling, he’s known to live many lives under one face.

Charlie Sheen & gambling – a rundown of the affair

  • His ex-wife, the Hollywood sensation Denise Richards said that Sheen usually loses around $200,000 weekly to poor gambling choices. It was one of the reasons that led to their divorce.
  • Rumour has it that he was placing bets while taking his pregnant wife to the hospital during labour.
  • Gambling, along with his other addictions, lent a big hand to the decline of his acting career, and he eventually lost his role in the megahit television series Two and a Half Men.

Although Sheen retired from gambling in 2012, he was one of several celebrities caught on wiretapping conversations in the bust of a mafia-run gambling ring. However, he was exempted from any kind of legal action by the US authorities.

Charlie Sheen’s volatile mood swings

During an interview with the New York Times, Sheen revealed his biggest gambling win was from a boxing bout between Manny Pacquiao and Oscar De La Hoya.

He put a mind-boggling wager of $1 million on Pacquiao. The more interesting thing was his reaction after winning that mammoth bet.

It’s also interesting to see his volatile mood swings, even when he loses.

Nicole Kidman is one smart celebrity gambler

Nicole Kidman is one smart celebrity gambler
Source: vogue.co.uk

Known for many hits in Hollywood, Nicole Kidman revealed her secret gambling talent in 2016.

However, she is cautious when placing her bet, as she stakes significantly less money in casinos.

Celebrity gambler & movie star:

  • Nicole Kidman is one of the many star celebrity gamblers spotted in the high-end Star Casino in Australia to indulge in various table games.
  • Nicole and Keith both admitted enjoying jaunts to Las Vegas casinos, and her husband appreciated her for being a very good gambler.

Shannon Elizabeth: the celebrity addict who cashed in serious money

Shannon Elizabeth
Source: imdb.com

The American actress, model, and animal activist Shannon Elizabeth’s interest in poker grew from a hobby to a full-fledged career, earning her name as one of the leading celebrity poker players in 2006.

The story’s main moments:

  • Shannon was inclined towards playing poker with her family from a young age and gradually got addicted to gambling as she confessed to having visited Las Vegas casinos two or three times a month.
  • She participated in the 4th edition of Celebrity Poker Showdown. She won $50,000 after defeating 83 other celebrities in the inaugural Nicky Hilton New Year’s Eve Poker Tournament.
  • In 2007, she participated in the NBC National Heads-Up Poker Championship semi-finals before losing to Paul Wasicka, who won the tournament.
  • Since winning 12 tournaments between 2006 and 2010, Elizabeth doesn’t seem to have been an active poker player except for cashing in one poker tournament in 2013.

Famous gambling addicts

Gladys Knight

Gladys Knight
Source: gladysknight.com

The American singer, actress, and seven times Grammy Award winner, Gladys Knight, was introduced to the gambling world with a blackjack game by one of her old friends.

Initially, it was fun and casual for her, but soon began a cause of distress as she grew addicted to gambling.

Knight’s gambling addiction was interfering with her life as a mother, and there were two such instances where she lost $45,000 and $60,000 at the table. She finally asked for help from Gambler’s Anonymous meetings to break free from her compulsive gambling habit.

Charles Barkley

Charles Barkley
Source: golfdigest.com

Former NBA star and sports analyst Charles Barkley was a gambling enthusiast who had lost almost $10 million through wagering and a complaint in his name for allegedly failing to pay his $400,000 debts.

Despite losing millions on gambling, whether sports betting or blackjack, he argued that he could afford to support his gambling addiction.

However, after incurring huge losses at gambling and repaying his debt, he admitted to having realised the need to quit playing.

Even celebrities must set some boundaries

Casinos have always been a go-to choice for celebrities. We’ve even compiled of celebrities banned from casinos across the years.

Although most celebrity gamblers grow an affinity towards poker, blackjack, and sports betting as a leisure activity, it soon can overpower and derail most celebrity life if not kept under control.

The empire of cash that most famous celebrities build also arouses their habits. Therefore, you keep in mind that you play responsibly. Problem gambling can destroy your life as you know it, even if you are a celebrity.

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Anca Iamandi
AuthorAnca IamandiSenior Author & Editor at CasinoAlpha

Anca's analytic skills developed in Generative Linguistics allow her to bring you clear and concise gambling-related content. Her texts will help you understand casinos, bonuses, fees, and rules and forget about all the gambling myths that pull you down. She's a strong advocate of safe gambling.

Tudor Turiceanu
ReviewerTudor TuriceanuCEO & Chief Editor at CasinoAlpha

Tudor Turiceanu uses his multiple systematic skillsets to oversee and coordinate the CasinoAlpha project. He assists the authors in creating a transparent gambling niche for users. As a CEO and Chief Editor with broad knowledge, Tudor knows the importance of transmitting confident advice.