You can't help but feel for Benjamin "Lefty" Ruggiero in director Mike Newell's 1997 mob drama Donnie Brasco. A 30-year wiseguy, he's never been able to rise above being the Bonanno crime family's go-to hit man, and, at home, his son is addicted to drugs and his personal finances aren't up to snuff.
When FBI agent Joseph Pistone (Johnny Depp) goes undercover to smoke out the Bonanno crew, he quickly takes a liking to the sympathetic, seasoned Ruggiero. Their friendship anchors the film and lends it a tragic energy, since, once Pistone finishes his job, Ruggiero's world will go from undesirable to decimated.
Always so damn good playing louder, larger-than-life characters, Pacino is just as masterfully efficient when he tones it down. As Lefty Ruggiero, he's able to generate empathy for a Cosa Nostra member who, you know, has killed over 20 people in his lifetime.