3. Ray Liotta as Henry Hill, Goodfellas (1990)
He's the orator of the immortal opening lines from master director Martin Scorsese's Goodfellas, arguably the greatest mobster movie ever made: "As far back as I can remember, I always wanted to be a gangster." And that's exactly what Henry Hill (Ray Liotta) became, working his way into the operation ran by Irishman Jimmy Conway (Robert De Niro, playing a character based on real-life criminal Jimmy Burke), an associate of mob boss Paul Cicero (Paul Sorvino, who's role was based on Paul Vario).
Unlike the other gangsters on this list, Henry Hill is seen in Goodfellas as a vulnerable, at times scared regular guy who joined the mob more for idol worship (he grew up in awe of the local Lucchese crime family in East New York, Brooklyn) than sheer bloodlust. As played by Liotta, he's no pushover, either, evidenced by a scene in which he nearly beats a guy to death for messing with his girlfriend (Lorraine Bracco).
Mostly, though, Hill serves as the audience's conduit, watching in both horror and wonderment as his associates, namely hot-headed Tommy DeVito (Joe Pesci, who's character is based on Thomas DeSimone), kill and brutalize like it's nothing. It comes as no surprise—aside from the fact that Goodfellas is based on Nicholas Pileggi's non-fiction book Wiseguy, about Hill's life—Hill eventually sells Conway out to the FBI and heads into the Witness Protection Program to save his and his family's asses.
Hill "always wanted to be a gangster," but, as sold wonderfully by Liotta, he wasn't entirely built for it.