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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.
A month later, while on parole, he trespassed into a neighbor's home while under the influence of a controlled substance, and fell asleep in one of the beds.
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.
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.