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Movies like Liberty Heights (1999)

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.