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Zero drove Downey into films with bigger budgets and names, such as Chances Are (1989) with Cybill Shepherd and Ryan O'Neal, Air America (1990) with Mel Gibson, and Soapdish (1991) with Sally Field, Kevin Kline, and Whoopi Goldberg.
In 1992, he starred as Charlie Chaplin in Chaplin, a role for which he prepared extensively, learning how to play the violin and tennis left-handed.
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.
That same year, Downey had a dramatic acting breakthrough when he played James Spader's sidekick in Tuff Turf and then a bully in John Hughes' Weird Science.Making his acting debut at the age of five, appearing in his father's film Pound (1970), Downey Jr.