In 1990, Scott played a lead role in the ground-breaking film Longtime Companion, which chronicles the early years of the AIDS/HIV epidemic and its impact upon a group of American friends. In the following year, Scott co-starred in the movie Dying Young (in which his mother also appeared) alongside Julia Roberts. He also appeared in the 1992 Cameron Crowe movie Singles alongside Bridget Fonda and Kyra Sedgwick, and in 1996, he teamed up with Stanley Tucci to direct the film Big Night. The film met with critical acclaim and was nominated for the "Grand Jury Prize" at the Sundance Film Festival. For their work, Scott and Tucci won both the New York Film Critics Circle Award and the Boston Society of Film Critics Award for Best New Director.