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He was considered for the role of Duckie in John Hughes' film Pretty in Pink (1986), but his first lead role was with Molly Ringwald in The Pick-up Artist (1987).

Because of these and other coming-of-age films Downey did during the 1980s, he is sometimes named as a member of the Brat Pack.

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

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