Back in New York, Rubin worked first as an associate curator and later advanced to head of the film department at the Whitney Museum. He and his wife (an art professor) next moved to the Midwest where he earned his graduate degree and wrote a screenplay, "The George Dunlap Tape". He planned to direct it himself, but once the financing fell through, it was optioned by Douglas Trumbull and was eventually made into Natalie Wood's swan song, "Brainstorm" (1983). The film's most memorable sequence depicted the dreamy sights and sounds of a woman's after-death experience.
Frustrated by his inability to work with Hollywood from the Midwest, Rubin moved to L.A. His first produced screenplay, "Deadly Friend" (1986), directed by Wes Craven, was an oddball teen horror film about a bright young lad who reanimates his dead girlfriend. 1990 was Rubin's breakthrough year: he wrote and served as associate producer on both "Ghost" and "Jacob's Ladder". The former featured Patrick Swayze as a murder victim who has unfinished business with his girlfriend (Demi Moore). This diverting romantic fantasy grossed over $200 million and netted a Best Screenplay Oscar for Rubin. The less successful, but more ambitious, "Jacob's Ladder" depicted the surreal hallucinations of a Vietnam vet trying to cope with life and love as a civilian. The film was abetted by the glossy direction of Adrian Lyne and a powerful central performance by Tim Robbins.
Rubin also contributed to the psychodramas "Deceived" and "Sleeping with the Enemy" (both 1991). Unhappy with the results, he was credited as "Derek Saunders" for the former and uncredited for the latter. At the age of 50, Rubin finally made his solo directorial debut with "My Life" (1993), an emotional drama starring Michael Keaton as a terminally ill man preparing for death by videotaping his final months for his unborn child.