A versatile, young, blond performer, Rapaport segued smoothly from standup comedy to acting with a 1990 guest shot on ABC-TV's "China Beach" and a starring role in "Zebrahead" (1992) as a white high schooler involved in a tense interracial relationship. For the latter, he garnered good notices and an Independent Feature Project Spirit Award nomination. More TV work followed including a recurring role on the fleeting but acclaimed comedy-drama "Middle Ages" (CBS, 1992).
Rapaport's film career took off in 1993 with appearances in four diverse projects, including the delirious Quentin Tarantino-scripted crime adventure "True Romance". Playing the edgy actor friend of Christian Slater, Rapaport held his own amid the formidable ensemble. He also had a small role in writer-director John Singleton's "Poetic Justice" that year. Rapaport graduated to a major role in Singleton's "Higher Learning" (1995) playing a not entirely unsympathetic Midwestern college student who becomes a skinhead in a misguided effort to forge an identity for himself. Later that year, he won praise for his role as a not-too-bright boxer being set up with a prostitute in Woody Allen's "Mighty Aphrodite". In Ted Demme's "Beautiful Girls" (1996), Rapaport was Matt Dillon's roommate who was fixated on models. He appeared in supporting roles in "The Pallbearer" (1996), "A Brother's Kiss" (1997) and headlined Nick Gomez's "illtown" (1998).