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Despite Downey's lawyer, John Stewart Holden, assembling for his client's 1999 defense the same team of lawyers that successfully defended O. Simpson during his criminal trial for murder, Downey was sentenced to a three-year prison term at the California Substance Abuse Treatment Facility and State Prison in Corcoran, California.

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

After Downey missed another required drug test in 1999, he was arrested once more.

Despite the apparent success, Downey claims 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.

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.

Beginning in 2008, Downey began portraying the role of Marvel Comics superhero Iron Man in the Marvel Cinematic Universe, appearing in several films as either the lead role, member of an ensemble cast, or in a cameo. domestic box-office grosses of Downey Jr.'s films total over US $4.2 billion, with worldwide grosses surpassing $9.6 billion, making Downey Jr. Downey later stated that drug use became an emotional bond between him and his father: "When my dad and I would do drugs together, it was like him trying to express his love for me in the only way he knew how." Eventually, Downey began spending every night abusing alcohol and "making a thousand phone calls in pursuit of drugs".