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Ray Romano -

Comedian and actor Ray Romano gave an interview in 2011, before the World Series of Poker, in which he admitted to a betting problem.

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Ray Romano -

He described how his real life experience had helped him to play a compulsive gambler in the TV series 'Men of a Certain Age.' He joined Gamblers Anonymous to kick the habit.

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Gladys Knight -

Singer Gladys Knight, who is known to many as the Empress of Soul, suffered for nearly ten years from a gambling addiction to the game baccarat.

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Gladys Knight -

In the late 1980s, following a particularly bad loss, Knight joined Gamblers Anonymous and managed to kick the habit. She wrote about it in her autobiography.

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Michael Phelps -

In 2012 there were rumors that decorated Olympian Michael Phelps had a problem with gambling. Rumors were started when friends professed to be worried about him.

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Michael Phelps -

According to those close to him, Phelps had a gambling problem so bad that they were worried he could "squander millions away."

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Nelly -

In 2011 Nelly's former manager, Slim, blasted the rapper in the media, claiming that he had lost all his money to gambling and that he was abusing drugs.

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Nelly -

Nelly refuted the claims and they were never proven true. He was in the media again in 2020, though, this time for ranting at a pit boss inside a casino.

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Charles Barkley -

Former NBA star Charles Barkley is known to be a compulsive gambler. In 2007 he told an ESPN interviewer that he had lost approximately US$10 million to his habit.

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Charles Barkley -

In May 2008 the Wynn Las Vegas casino filed a complaint about Barkley for failing to pay a US$400,000 debt. After that Barkley said he'd give the gambling a break.

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Tobey Maguire -

Whether Tobey Maguire's penchant for poker can be described as a problem is up for debate, but we do know he is partial to a high stakes game.

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Tobey Maguire -

He was one of a number of celebrities, who also included Leonardo DiCaprio and Ben Affleck, who competed in Molly Bloom's high-stakes games at The Viper Room in the 2000s.

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Pamela Anderson -

In 2007 Pamela Anderson gave viewers of the 'Ellen DeGeneres Show' an insight into her relationship with poker.

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Pamela Anderson -

She told the talk show host that she had made  a deal with poker pro Rick Salomon (whom she would later marry) to pay off a US$250,000 debt with sexual favors.

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Charlie Sheen -

When Charlie Sheen and ex-wife Denise Richards were in the middle of their divorce, she gave a sworn statement in which she referred to Sheen's gambling problem. 

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Charlie Sheen -

The 'Two and a Half Men' actor apparently placed sports bets every day, had lost hundreds of thousands of dollars, and would have violent mood swings when he lost.

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Ben Affleck -

Actor Ben Affleck has been known to gamble professionally, even qualifying for the 2004 World Poker Tour final tournament. He has always denied addiction, however.

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Ben Affleck -

But in 2014, Affleck was banned from playing blackjack at the Hard Rock Hotel in Las Vegas, among suspicions that he was using the frowned upon technique of counting cards.

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Matt Damon -

As previously mentioned, Matt Damon was in the ring at The Viper Room. He has a very public relationship with the game of poker.

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Matt Damon -

He also starred across from Edward Norton in what is now considered one of the best poker movies of all time: 'Rounders' (1998).

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Michael Jordan -

When former NBA star Michael Jordan's career came to an end in 2013, there were rumors that it was because of a gambling addiction.

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Michael Jordan -

Indeed, MJ had been seen out gambling and in 2005 he told Ed Bradley of '60 Minutes' that he had made some reckless decisions.

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Allen Iverson -

Allen Iverson is another former professional basketball player who appears to have a bit of a problem with gambling.

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Allen Iverson -

Sources suggest that his problem caused him to be banned from casinos in Detroit. He is also believed to struggle with alcohol addiction.

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Shannon Elizabeth -

Not so much gambling addict as professional poker player, actress Shannon Elizabeth, who is best known for her role in the 'American Pie' franchise, found a second career in the game.

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Shannon Elizabeth -

The actress found a huge amount of success as a poker player and has been described as "one of the leading celebrity poker players."

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Phil Mickelson -

Pro golfer Phil Mickelson is known for a number of things, not least for being a title-winning golfer with a left-handed swing.

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Phil Mickelson -

He is also, unfortunately, known for his gambling habit, and over the years rumors have circulated that could be described as Mickelson having near legendary status when it comes to gambling.

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Tiger Woods -

Tiger Woods joins Phil Mickelson in the ranks of pro golfers rumored to have a gambling problem. 

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Tiger Woods -

At the same time as he was embroiled in an infidelity scandal back in 2010, rumors circulated that Woods would play at high stakes blackjack tables and bet US$250,000 per hand.

Sources: (Ranker) (The Hollywood Reporter) (TMZ)

See also: Movies that deal with gambling

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