Charlie Sheen

Considering the laundry list of vices and moral failings that actor Charlie Sheen has gleefully admitted to over the years, one wouldn’t suspect that his penchant for sports betting would cause serious problems. After all, Sheen made waves in 2011 by smoking crack cocaine on camera, and just recently was forced to admit that had knowingly been HIV-positive during much of his sex-fueled heyday in Hollywood’s limelight.

But in addition to Sheen’s more well-publicized issues with alcoholism, drug addiction, and sexual promiscuity, he has also been accused of becoming hooked on the rush provided by high-stakes sports wagers. During his divorce from actress Denise Richards in 2006, documents unsealed at the time indicated that Richards was seeking dissolution of the marriage due to, among many significant issues, Sheen’s ongoing gambling addiction.

Six years later, in June of 2012, Sheen was interviewed by the New York Times’ Arts & Leisure section, and he was not shy when recounting the biggest bet of his life:

Million dollars. Pacquiao. It was a wrong-way spread and I had a dream a week before that he was going to beat De La Hoya like a drum, and he did. Second round, the punch score was like 300 to 2. And it was like, pfffft, whatever. I felt nothing. And I went, O.K., there’s nothing left for me here. Unless my children are involved in the wager, no sense in making it, you know?

During the same interview Sheen also claimed to have kicked his urge to visit the sportsbook:

I don’t bet anymore. I’m a retired gambler. Not a recovering gambler. Big difference. I’ll still look at the lines. I’ll be like, yeah, that’s a blowout, that’s a 40-point blowout. Easy, right? I’ll watch the game. It’s 40-point blowout the other way, and I can just walk away. I don’t have some dude calling, like, ‘Hey, yeah, so tomorrow, huh?’

Charlie Sheen was born as Carlos Irwin Estévez on September 3rd, 1965 in New York City. As the son of Hollywood heavyweight Martin Sheen (born as Ramón Antonio Gerardo Estévez), Charlie took an Americanized stage name just as his father had decades before. The younger Sheen grew up with actors to be Rob Lowe and Sean Penn as childhood pals, and by 1984 he landed his first role in a feature film, the Cold War drama Red Dawn.
During the 1980s Sheen ascended to the height of Hollywood stardom, starring in the Vietnam War drama Platoon in 1986, followed by Wall Street in 1987. Starring alongside his father, Sheen drew critical raves for his work. A string of appearances in hit comedies like Major League (1989), Men at Work (1990), Hot Shots! (1991) displayed Sheen’s wide range, while expanding his appeal to mainstream audiences.

Sheen remained a successful film actor throughout the 1990s, but his real reputation was gained behind the scenes, where tales of his drug-fueled excesses and preference for porn stars drove intense tabloid coverage. In 1995 Sheen’s first marriage, to Donna Peele, fell apart after he was named by Hollywood madam Heidi Fleiss as a longtime client of her high-priced escort service.

In 2003 Sheen accepted a role as the lead on a television series called Two and a Half Men. Playing a loose caricature of himself in “Charlie Harper” – a California-based bachelor with hedonistic tendencies and money to burn – Sheen led the show to astounding ratings despite the fact that Two and a Half Men was universally panned by critics. By the time Sheen was dismissed from the show, and Warner Bros. Studio altogether, in 2011, he had become the highest-paid actor on television, earning a reported $1.8 million per episode.

Sheen’s dismissal from Warner Bros. Studio took place after the actor entered rehabilitation for substance abuse for the third time in just 12 months. Further deepening the divide between himself and his employer, Sheen vocally demanded a 50% raise in his per episode wage, while also subjecting studio head Chuck Lorre to an anti-Semitic rant:

What does this say about Haim Levine [Chuck Lorre] after he tried to use his words to judge and attempt to degrade me… I fire back once and this contaminated little maggot can’t handle my power and can’t handle the truth. I wish him nothing but pain in his silly travels especially if they wind up in my octagon. Clearly I have defeated this earthworm with my words – imagine what I would have done with my fire breathing fists.

Sheen’s career spiraled out of control following his termination from Two and a Half Men, and around the same time he began releasing bizarre videos of himself online, many of which included footage of Sheen smoking crack cocaine. The online broadcasts provided Sheen with a temporary return to the public eye, but more than his fading stardom, audiences were much more interested in sampling the pure schadenfreude of a man willfully marching himself toward rock bottom with his camera in tow. One of Sheen’s many catchphrases during these publicized displays of manic behavior was “Winning!” – perhaps a veiled reference to his imagined exploits at the sportsbook.

During his divorce from Richards in 2006, the actress revealed that Sheen spent at least $20,000 on sports bets every weekend. According to Richards, Sheen’s sports gambling habit took precedence over both his marital obligations and his responsibility to raise the couple’s two daughters.

In 2011, during the height of Sheen’s crack cocaine and hooker binges, the online sportsbook offered a series of proposition wagers on the actor’s future behavior. Among the bets offered by at the time were 6 to 5 odds that Sheen would be arrested within the next three months, 2 to 1 odds that he would be arrested on charges of rape, and 25 to 1 odds that he would eventually be committed to a mental institution.