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He starred as the title character in the 1992 film Chaplin, which earned him a nomination for the Academy Award for Best Actor and won him the BAFTA Award for Best Actor in a Leading Role.After being released in 2000 from the California Substance Abuse Treatment Facility and State Prison where he was on drug charges, Downey joined the cast of the TV series Ally Mc Beal playing Calista Flockhart's love interest. His character was written out when Downey was fired after two drug arrests in late 2000 and early 2001.and went several times through drug treatment programs unsuccessfully, explaining in 1999 to a judge: "It's like I have a shotgun in my mouth, and I've got my finger on the trigger, and I like the taste of the gun metal." He explained his relapses by claiming to have been addicted to drugs since the age of eight, due to the fact that his father, also an addict previously, had been giving them to him.In April 1996, Downey was arrested for possession of heroin, cocaine, and an unloaded .357 Magnum handgun while he was speeding down Sunset Boulevard.Despite the apparent success, Downey claimed that his performance on the series was overrated and said, "It was my lowest point in terms of addictions.At that stage, I didn't give a fuck whether I ever acted again." Before the end of his first season on Ally Mc Beal, over the Thanksgiving 2000 holiday, Downey was arrested when his room at Merv Griffin's Hotel and Givenchy Spa in Palm Springs, California was searched by the police, who were responding to an anonymous 911 call.In 1987, Downey played Julian Wells, a drug-addicted rich boy, whose life rapidly spirals out of his control, in the film version of the Bret Easton Ellis novel Less Than Zero.His performance, described by Janet Maslin in The New York Times as "desperately moving", was widely praised, though Downey has said that for him "the role was like the ghost of Christmas Future" since his drug habit resulted in his becoming an "exaggeration of the character" in real life.



Downey Jr.'s career prospects improved when he featured in the black comedy crime Kiss Kiss Bang Bang (2005), the mystery thriller Zodiac (2007), and the satirical action comedy Tropic Thunder (2008); for the latter he was nominated for an Academy Award for Best Supporting Actor. His father, Robert Downey Sr., is an actor and filmmaker, while his mother, Elsie Ann (née Ford), was an actress who appeared in Downey Sr.'s films.He had a personal coach in order to help him imitate Chaplin's posture, and a way of carrying himself.In 1993, he appeared in the films Heart and Souls with Alfre Woodard and Kyra Sedgwick and Short Cuts with Matthew Modine and Julianne Moore, along with a documentary that he wrote about the 1992 presidential campaigns titled The Last Party (1993).When his parents divorced in 1978, Downey moved to California with his father, but in 1982, he dropped out of Santa Monica High School, and moved back to New York to pursue an acting career full-time.

Downey began building upon theater roles, including in the short-lived off-Broadway musical American Passion at the Joyce Theater in 1983, produced by Norman Lear.

In 1997, he missed one of the court-ordered drug tests, and had to spend six months in the Los Angeles County jail.