After a decade of attending college and appearing in Off-Broadway theatre, Chianese attended his first professional acting class at HB Studio in Manhattan, with renowned Teacher Walt Witcover. Drama and musical theater became Chianese's passion. His first Broadway show was Oliver! in 1965. He has continued to perform in Broadway theatre, Off Broadway, and regional theatre. To supplement income in the dry periods, he played rhythm guitar and sang in taverns and restaurants. Chianese's first television credit occurred when George C. Scott recommended him for a role in the acclaimed series East Side/West Side. In 1974, Francis Ford Coppola cast Chianese as Johnny Ola in The Godfather Part II, which sparked a film career, culminating in several films (and plays) with Al Pacino.