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His breakthrough role was as Benjamin Braddock in Mike Nichols' critically acclaimed and iconic film The Graduate (1967), for which he received his first Academy Award nomination. His next role was "Ratso" Rizzo in John Schlesinger's Midnight Cowboy (1969), in which he acted alongside Jon Voight; they both received Oscar nominations, and the film went on to win the Academy Award for Best Picture. He gained success in the 1970s playing roles that shaped the craft of his acting, crossing genres effortlessly in the western Little Big Man (1970), the prison drama Papillon (1973), playing a controversial and groundbreaking comedian in Bob Fosse's Lenny (1975), Marathon Man alongside Laurence Olivier (1976), and as Carl Bernstein investigating the Watergate scandal in All the President's Men (1976). In 1979, Hoffman starred in the family drama Kramer vs. Kramer alongside Meryl Streep. They both received Academy Awards for their performances.

After a three-year break from films, Hoffman returned in Sydney Pollack's show business comedy Tootsie (1982) about a struggling actor who pretends to be a woman in order to get an acting role. He returned to stage acting with a 1984 performance as Willy Loman in Death of a Salesman and reprised the role a year later in a television film earning a Primetime Emmy Award. In 1987 he starred alongside Warren Beatty in Elaine May's comedy Ishtar. He won his second Academy Award for Best Actor for his portrayal of the autistic savant Ray Babbitt in the 1988 film Rain Man, co-starring Tom Cruise. In 1989, he was nominated for a Tony Award and a Drama Desk Award for playing Shylock in a stage performance of The Merchant of Venice. In the 1990s, he made appearances in such films as Warren Beatty's action comedy adaptation Dick Tracy (1990), Steven Spielberg's Hook (1991) as Captain Hook, medical disaster Outbreak (1995), legal crime drama Sleepers (1996), and the satirical black comedy Wag the Dog (1997) alongside Robert De Niro.