Donnie Brasco (1997)

Posing as jewel broker Donnie Brasco, FBI agent Joseph D. Pistone (Johnny Depp) is granted entrance into the violent mob family of aging hit man Lefty Ruggiero (Al Pacino). When his personal and professional lives collide, Pistone jeopardizes his marriage, his job life, and, ultimately, the gangster mentor he has come to respect and admire. From acclaimed director Mike Newell (Four Weddings and a Funeral), and featuring an extraordinary supporting cast including Michael Madsen, Anne Heche, Bruno Kirby, and James Russo.