Legendary Gamblers: Charlie Sheen

In the turbulent world of Hollywood, few names conjure as much controversy and intrigue as that of Charlie Sheen. However, it's not just his acting prowess that has garnered attention; Sheen's penchant for high-stakes gambling has also earned him a reputation as a legendary player in the world of betting. Let's dive into what makes Charlie Sheen's gambling adventures so legendary...

Who is Charlie Sheen?

Known for his A-list performances on-screen, and flamboyant yet controversial off-screen persona, Sheen has been a staple in the entertainment industry for decades. From his early roles in iconic films like Platoon and Wall Street to his memorable stint on the hit TV series Two and a Half Men, Sheen has left an indelible mark on popular culture.

Meanwhile, despite all of his success he is also known to have quite the addictive personality... whether it was drugs, cigarettes, alcohol, women, or gambling, Sheen was probably addicted to it at some point.

What Makes Charlie Sheen’s Gambling So Legendary?

Sheen's gambling escapades are the stuff of legends, with tales of his brazen wagers and fearless attitude making their way through Hollywood circles.

Placing a $1m Wager on Manny Pacquiao

An incredible example of this devil-may-care approach, to how Sheen gambles, is when he placed a $1 million bet on boxer Manny Pacquiao to beat Oscar De La Hoya, in their matchup back in 2008. Sheen said in an interview with the New York Times that it was the biggest wager he had ever made.

The result left him feeling very blasé as he stated that he knew that Pacquiao would win, as he saw it in a dream.

“I had a dream a week before that he was going to beat De La Hoya like a drum, and he did. It was like, pfffft, whatever. I felt nothing.”

It is unclear how much he won off the back of this $1m bet, but Sheen wasn't phased at all. To most, a million-dollar bet would be life-changing but for Sheen, it was just another Saturday.

Starring in Gambling-Related Movies

His love and enthusiasm towards sports betting has even spilled over into his professional career. Just this past year, he joined the cast of the new television series Bookie, showing an affinity for passion of sports betting in media once again. Bookie is a dramedy, that came out in November 2023, about a bookie providing illegal sports betting in California, and the unpredictable and unstable clients that come with operating that sort of business.

This isn’t the first time where Sheen had made a wager in a movie or in a television show. In Eight Men Out, Sheen portrays "Happy" Felsch, one of the members who infamously bet on the Chicago White Sox during the 1919 Black Sox Scandal.

Charlie Sheen’s Biggest Gambling Controversies

While Sheen seems to be able to brush off a million-dollar sports betting win, his gambling career is certainly anything but spotless...

Ex-Wife Divorcing Him Due to Sports Betting Habits

Sheen has been known by many to be a big lover of sports betting. No sport seems to be too big or too small for Sheen as he has wagered on the top-tier sports like basketball, baseball, and football and some of the more niche sports like badminton and darts.

His love for sports betting knows no bounds, as his ex-wife Denise Richards once told a story about Sheen where he was making phone calls in the car to bookies to place bets on various games. The only issue with this is that he was making wagers on the way to the hospital for the birth of his child.

His ex-wife, Richards, had a lot to say about Sheen and his out-of-control gambling during their marriage. Infamously, Richards once claimed that Sheen would gamble on both casino games and sports every day, in excess of $200,000 a week. Additionally, when he lost he would go into fits of rage and would exert "volatile mood swings". This, and various other factors, led the couple to divorce in 2006.

Bookies Making Odds on Sheen's Next Move

The demise of Charlie Sheen... 2010 was the start to the downfall of Sheen’s career. In August, he pleaded guilty to misdemeanor assault on his ex-wife Brooke Mueller. In October, he was removed from the Plaza Hotel in New York after causing $7,000 in damage while being high on cocaine.

This led to BetUS.com capitalizing on the latest Sheen news by placing odds on potential felonious charges. For example, there was a wager on where Charlie Sheen would get arrested next. Las Vegas had the best odds at 3/2 while Moscow had the longest at 5/1.

The site also had another bet where you could make a wager on what Sheen would be arrested for next. The best odds were 5/6 for prostitution while the longest odds were 5/1 for gun possession. The site also put him being arrested for any charge in the next three months, at 5/6 odds; while him being put into a mental institution would have a great payout at 25/1 odds.

Being Involved With a Mafia Betting Sting

To make matters worse for Sheen’s betting escapades, the high-profile star was named alongside other celebrities in a mafia gambling sting in late 2016. Names like James Caan, Tony Danza, and Larry David were also mentioned in the story; as customers who may have been on the police’s wiretaps making bets.

All in all, 13 mafia members were arrested including notorious mob member Salvatore “Sallie” DeMeo. No celebrities were ever charged in the sting but one has to wonder about Sheen’s involvement in the whole operation due to his gambling past.

Where is Charlie Sheen Now?

Based on his relative lack of enthusiasm after his gigantic win on Manny Pacquiao, it seems very clear that Sheen doesn’t seem to get much pleasure from sports betting anymore.

In early 2011, Sheen announced that he was done with his betting career. He was quoted in the New York Times, saying:

“I don’t bet anymore. I’m a retired gambler. Not a recovering gambler. Big difference.”

Additionally, as mentioned previously, he is now starring in the new show Bookie, having buried the hatchet with Two and a Half Men creator, Chuck Lorre.

Given the fact that this is ultimately a show about sports betting, time will only tell if Sheen feels like getting back to his gambling ways, and makes a wager or two once the show is wrapped up. For now though, let’s hope that Bookie is the start of a new chapter in Sheen’s career, with more movies and television shows underway; with less distractions.