Rapp was born in Chicago, Illinois, and raised in nearby Joliet, Illinois, the son of Mary Lee (née Baird) and Douglas Rapp. After his parents\' divorce in 1974, he was raised by his mother, a trained nurse. His older brother is playwright, novelist, and filmmaker Adam Rapp. He also has an older sister.\n', '

Rapp participated in community theater as a child and won numerous awards for his singing in junior high school. Rapp attended high school at Joliet West High School and theatre camp at Interlochen Arts Camp in Michigan. He moved to New York in 1989 to attend New York University as a film student, but dropped out after a semester.\n', '

Rapp first performed on Broadway in 1981 in The Little Prince and the Aviator, a musical based on Antoine de Saint-Exupéry\'s novel The Little Prince. The show closed during previews. His screen debut was as a member of the starring ensemble in the 1987 film Adventures in Babysitting, directed by Chris Columbus, who would later direct him in the film version of Rent. He has appeared in several movies and Broadway shows. His notable roles includes such films as Dazed and Confused, A Beautiful Mind, School Ties, Road Trip, Six Degrees of Separation (stage and film versions), An American Family, Danny Roane: First Time Director and You\'re a Good Man, Charlie Brown.\n', '

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