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, and also served as the master of ceremonies at the open microphone night at Gerdes Folk City in Greenwich Village. 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.

Chianese is an accomplished tenor and musician, having released a CD titled Hits in 2000, on which he sings American and Italian songs. He performed Salvatore Cardillo’s sentimental classic “Core ‘ngrato” (“Ungrateful Heart”), on the third-season finale of The Sopranos (episode 3.13, “Army of One”). In 2003, Chianese, along with AOL Music, released a second CD titled Ungrateful Heart, which features 16 classic Neapolitan songs. In the 2000s he played in a mandolin quartet weekly at the Hotel Edison, New York City.

In 2010, Chianese received the Ellis Island Medal of Honor in recognition of his humanitarian efforts.

In December 2018, Chianese and co-author, Matthew Sargent, published the biography of Chianese’s improbable rise to the top, Twelve Angels: The Women Who Taught Me How to Act, Live, and Love, distributed by Simon & Schuster.