His third film with Scorsese, the 1977 musical New York, New York, marked a departure from his usual dark fare—he played a jazz musician who becomes romantically involved with a singer, played by Liza Minnelli. De Niro’s potrayal of a Green Beret in The Deer Hunter (1978) earned him a second Best Actor nod. In 1980, De Niro took on his most challenging part yet (at least physically), gaining 50 pounds to play boxer Jake LaMotta in Scorsese’s Raging Bull, based on LaMotta’s autobiography. The role garnered him an Academy Award for Best Actor. The film, now considered a classic, was nominated for eight Oscars in all, including Best Picture, Best Director, and Best Supporting Actor (Joe Pesci, who played LaMotta’s brother).

For the next 10 years, De Niro branched out into a number of different types of films, with varying degrees of success. He co-starred with Jerry Lewis in Scorsese’s The King of Comedy (1983) and with James Woods and Pesci in the mob drama Once Upon a Time in America (1984). He gamely tried his hand at romantic drama (starring opposite Meryl Streep in 1984’s Falling in Love); science-fiction/fantasy (1985’s Brazil); and historical drama (1986’s The Mission).

De Niro had more success in 1987, when he reunited with De Palma in The Untouchables, appearing as Al Capone opposite Kevin Costner as FBI agent Eliot Ness. The next year, he scored a huge hit with the action-comedy Midnight Run (1988), co-starring Charles Grodin as the white-collar criminal De Niro’s bounty hunter attempts to bring from New York to Los Angeles after he jumps bail.

In 1988, De Niro bought a former coffee factory just a few blocks from his loft in the TriBeCa neighborhood of Manhattan and converted it into the TriBeCa Film Center, headquarters for Tribeca Films, the production company that he founded with Jane Rosenthal. De Niro’s first project as an executive producer was a disappointing 1989 remake of We’re No Angels, written by David Mamet and co-starring De Niro and Sean Penn. De Niro earned a fourth Academy Award nomination for Best Actor in 1990 for Penny Marshall’s Awakenings, in which he starred as a patient who regains consciousness after 30 years in a coma. Robin Williams co-starred as the doctor who treats him; the film also earned nominations for Best Picture and Best Adapted Screenplay. He had even more success that same year with Scorsese’s Goodfellas, co-starring Joe Pesci and Ray Liotta—the story of three friends moving their way up in the hierarchy of the Mafia in New York.