Liberty Heights (1999)

You're only young once, but you remember forever.

This semi-autobiographical film by Barry Levinson follows various members of the Kurtzman clan, a Jewish family living in suburban Baltimore during the 1950s. As teenaged Ben completes high school, he falls for Sylvia, a black classmate, creating inevitable tensions. Meanwhile, Ben's brother, Van, attends college and becomes smitten with a mysterious woman while their father tries to maintain his burlesque business.