Charlie Sheen: Hollywood's baddest bad boy

It's amazing he has managed to do any acting at all, such has been his appetite for alcohol, cocaine and prostitutes. But will his latest indiscretion finally wreck his career? Don't bet on it

(Peter Brooker/Rex Features)

There's a well-known scene from Oliver Stone's 1987 film Wall Street in which the young Charlie Sheen has just purchased a Manhattan penthouse.

Flush from the success of Platoon the previous year, Sheen is at the height of his powers, embodying the naive investment banker Bud Fox as he decorates, eats dinner, then has sex with his beautiful girlfriend in their beautiful bed as a Talking Heads track plays in the background. At sunrise, he strides to the balcony to survey the universe of which he has just become a master, and then – in a clumsily didactic moment typical of Stone – asks himself out loud: "Who am I?"

Well might he ask. For, like Bud Fox, this was to be the peak of Sheen's career – or, more precisely, his reputation. In the recent Wall Street sequel, Money Never Sleeps, as Michael Douglas shone once more in the role of Gordon Gekko, Sheen was reduced to a clunking cameo. Two decades on, Bud Fox has become a louche, corrupted financier, who bumps into Gekko at a party with a young woman of questionable virtue on each arm.

The real Charlie Sheen, meanwhile, has been sucked again into the news cycle. This week, the 45-year-old actor allegedly took a porn star to dinner with his second ex-wife (of three), former Bond girl Denise Richards. Sheen then escorted the young lady, who goes by the stage name "Capri Anderson", back to his hotel room, which he duly trashed in an alcohol and drug-induced rage, accusing her of stealing his wallet. Police reportedly found Sheen pacing the suite naked, while Anderson cowered in the bathroom.

Sheen was released without charge and maintains that the tale has been overblown. His publicist made the only mildly believable claim that he reacted badly to medication. But it follows a pattern of past behaviour. Not only does the actor have a long history of dating porn stars, but he also once claimed to have spent $53,000 on prostitutes. In and out of rehab, he has admitted his twin poisons are vodka and cocaine.

Sheen ought, by rights, to be a laughing stock, yet he remains a powerful player in the entertainment world. His film career faded some time ago, but thanks to Two and a Half Men, the TV comedy in which he stars, he is the world's highest-paid sitcom actor. In late 2009, he was arrested and charged with domestic violence. His third wife, estate agent Brooke Mueller, claimed he had held a knife to her throat and warned her: "If you tell anybody I'll kill you... I have ex-police I can hire who know how to get the job done and they won't leave any trace."

Allegations of domestic abuse recently wrecked Mel Gibson's hopes of making a screen comeback. Yet Sheen completed his 30-day sentence in a rehab facility and, in May, signed a new contract with CBS for a further two years of Two and a Half Men – earning him an estimated $1.88m per episode. He did the deal without the assistance of an agent; WME had dropped him after he made unreasonable financial demands, and he is yet to sign with another firm. Like Bud Fox, his pockets are full, but his name is mud.

Sheen was born Carlos Estevez in September 1965. At the time, his father Martin Sheen (real name Ramon Estevez) was a jobbing stage and television actor, his mother Janet an artist. His two elder brothers Emilio and Ramon, and his younger sister Renée, would all go on to become actors. Charlie first appeared on screen aged eight, when his father got him a part alongside him in a TV movie, The Execution of Private Slovik. As his father's career took off, a teenage Charlie followed him to the Philippines to watch him shoot Apocalypse Now. But the production was traumatic, and Charlie saw Martin struggle with alcohol abuse and a non-fatal heart attack.

Sheen has called his father "the best guy I know, not just as a father, but as an individual". He suggests Martin's biggest mistake, however, was buying Charlie a new BMW for his 16th birthday. "I turned it into a party car," Sheen said recently, tracing the origins of his hellraising to that moment. He became a difficult, spoilt teenager, and was expelled from high school weeks before graduation. That didn't stop him from getting his high school sweetheart, Paula Profit, pregnant: their daughter Cassandra was born in 1984. "I wasn't exactly the best father," he confessed.

In 1985, Emilio became a star, courtesy of the John Hughes classic The Breakfast Club. But Sheen soon overtook his older brother when, in 1986, Oliver Stone cast him as the young lead in his ambitious anti-Vietnam movie Platoon. It was a fruitful partnership, earning Stone the Oscars for Best Picture and Best Director. It seemed natural, therefore, for Sheen to be cast as Bud Fox in Stone's next picture, about the wars on Wall Street. Yet in 1988, after Stone had supposedly approached his young star about returning to the theme of Vietnam in Born on the Fourth of July, the director changed his mind and cast Tom Cruise instead. Sheen may not have known it at the time, but his career was already on a downward slope.

In 1988, he starred with Emilio and a handful of their "Brat Pack" pals in the western Young Guns, and won praise in 1990 for his work alongside Clint Eastwood in The Rookie. But off-screen the cracks were starting to show. A poignant interview with the LA Daily News from 1987 has Sheen, still full of promise, claiming that he'd been "very fortunate in avoiding the Hollywood elements – drugs, seductions, the general craziness".

One of Sheen's childhood friends was Sean Penn who, at the time, was thought of as the bad body of the Brat Pack for the minor sin of hitting a photographer. But Sheen, who had in fact begun experimenting with drugs when he was 11, was already known by his friends as The Machine for his sustained ability to party. In 1990 he accidentally shot his fiancée, the actress Kelly Preston, in the arm; she left him soon after. With Eastwood's help, Martin organised an intervention to try to curb his son's extreme habits. It was only temporarily successful. The Rookie was Sheen's last serious film role. He was 25.

In the 1990s, Sheen became known instead for pastiche and self-parody, his most successful work of the period being the spoof war movies Hot Shots! and Hot Shots! Part Deux. In the meantime, his personal life was a mess. He was married (to Donna Peele), divorced, arrested and hospitalised for cocaine use. In 1997, his then-girlfriend Brittany Ashland accused him of having knocked her unconscious and threatened to kill her. He married Richards in 2002 after meeting her on a film set. The pair had two daughters, but divorced in 2005 with Richards complaining of drug abuse and more death threats.

At the turn of the millennium, Sheen's career had taken a turn for the better. Michael J Fox, suffering from Parkinson's disease, left a vacancy on the political sitcom Spin City, which Sheen filled to some acclaim. In 2002, he won a Golden Globe, with his father, also nominated for The West Wing, watching proudly from the stalls. Spin City ended soon afterwards, but Sheen was quickly cast as the charming, amoral bachelor Charlie in Two and a Half Men. The show was a critical train wreck, and a commercial super-hit.

His family remains close knit. Martin is currently promoting The Way, a new movie in which he stars, directed by Emilio. When Emilio's RFK biopic Bobby was criticised by one LA journalist, Charlie took it upon himself to email her suggesting she "go fuck [her]self". And Martin has always been there to shield his son from his self-destructive streak. After Sheen overdosed in 1998, it was he who reported him to the police for violating the terms of his probation. He even turned to the media, giving an interview in which he invited the public to pray for his troubled son. This week Martin has remained silent on Sheen's actions, though photographers noted the bumper sticker on his car. It read, "Non-violence is a family value."

A life in brief

Born: Carlos Irwin Estevez, 3 September 1965, New York.

Education: Expelled from Santa Monica High School, California, then Chaminade Catholic High School, Ohio.

Family: Son of actor Martin Sheen and artist Janet Templeton, he has one sister and two brothers, including the actor Emilio Estevez. Sheen has one child with Paula Profit, two with ex-wife Denise Richards and he is currently estranged from third wife, Brooke Mueller, with whom he has twins.

Career: First appeared on screen aged eight with father Martin in the TV movie The Execution of Private Slovik. Major roles in Platoon (1986) and Wall Street (1987) followed. Appeared in the spoof Hot Shots! films. In May 2010, he signed a new deal that made him the highest paid television actor, netting a rumoured $2m per episode of CBS sitcom Two and Half Men.

He says: "I was never shut down by the drugs; that was my problem. Cocaine was an aphrodisiac. I think that was a bit of a curse."

They say: "Pray for my boy; he has appetites that get him into trouble." Martin Sheen