Last Updated: April 6th

A good gangster movie must do two things: Make us want to live a life of crime and, at the same time, make us grateful we haven’t indulged our dark sides like the characters on this list. Most gangster films make the criminal underworld look like a hell of a good time. There’s booze, money, women, expensive cars, everything we’re taught we should want, but the lavish lifestyle often comes with a price, which means a good gangster movie must also show us the downside of running a criminal empire: The violence, the bloodshed, and the very real threat of prison time. As they say, you can’t have your cake and eat it too — but no one told that to the characters in these films.