Damn it Feels Good to be a Gangsta

They strut, they snarl, and they look damn fine while they do it. No matter how despicable their actions, these loveable son-of-a-guns somehow manage to charm their way into our hearts. Sadly, while they lead the pack in charisma, their life expectancy and likelihood of staying free men are almost nil.

Here are 8 movie gangsters who raised the bar for delinquency and helped make the genre what it is.

If you haven’t seen these movies you may want to stop reading. Then go stand in a corner and hang your head in shame, for there is no reason not to have seen any and all of these awesome gangster flicks.

Caesar Enrico Bandello (Edward G. Robinson in Little Ceasar, 1931)

Who he is: A pug-faced, small time hood who rises from the gutter to take over a criminal empire, only to crash and burn in a hail of machine gun fire. He’s also the unquestionable precursor to Joe Pesci’s portrayal of Tommy DeVito in Goodfellas.

Why he’s the best: A scrappy little bugger, he was one of the first movie characters to openly show contempt for the law.

Loses points for: Not killing the friend who betrays him. Pansy.

Memorable quote: “Mother of Mercy! Is this the end of Rico?”

Best threat: “Did you ever stop to think what you’d look like with a lily in your hand?”

Useless trivia: Rico utters one of the first movie lines censored to please the Hollywood suits. In the novel the line reads “Mother of God, is this the end of Rico?” The studio changed it out fear of being blasphemous. No problem with the violent murders though.

Tom Powers (James Cagney in The Public Enemy, 1931)

Who he is: A cocky, ruthless, thug who either slaps, punches, kicks, or shoots
everything that crosses his path. Pretty sexy.

Why he’s the best: So twisted he turns a grapefruit into a weapon and takes vengeance on a horse.

Loses points for: The striped pajamas

Memorable quote: “I ain’t so tough.”

Best threat: “There you go with that wishin’ stuff again. I wish you was a wishing well. So that I could tie a bucket to ya and sink ya.”

Useless trivia: The infamous grapefruit scene (supposedly improvised by Cagney) caused women’s groups around the country to protest the on-screen abuse of Mae Clarke. But according to Cagney’s autobiography Clarke’s ex-husband enjoyed it so much that he went to the movie theater everyday just to watch that scene and then leave. Other patrons were supposedly quite perturbed by his laughter.

Cody Jarrett (James Cagney in White Heat, 1949)

Who he is: Ruthless, criminal madman with seriously perverse, Oedipal-style mother issues.

Why he’s the best: Not just a bad guy with questionable morals, Cody represents the criminal as head case, both fascinating and frighteningly unstable.

Loses points for: Getting busted by an undercover cop. For shame.

Memorable quote: “Made it, Ma! Top of the world!”

Best threat: Roy Parker: ‘You wouldn’t kill me in cold blood, would ya?’ Jarrett: ‘No, I’ll let ya warm up a little.’

Useless trivia: The uncomfortably close relationship between Jarrett and his domineering mother was partly inspired by real life bank robbers Kate (Ma) Barker and her sons.

Michael Corleone (Al Pacino in The Godfather Trilogy)

Who he is: A reluctant prodigal son whose calm façade all but masks his cold-blooded inner nature.

Why he’s the best: His penchant for vengeance overrides any desire for legitimacy.

Loses points for: Marrying Kay. She clearly never had it in her to be a mafia wife. It takes a special kind of woman.

Memorable quote: “I don’t feel I have to wipe everybody out, Tom. Just my enemies.”

Best threat: “I know it was you Fredo. You broke my heart. You broke my heart!”

Useless trivia: Warren Beatty, Dustin Hoffman, Robert DeNiro, Jack Nicholson, Ryan O’Neal, Robert Redford, Burt Reynolds, Martin Sheen, and Rod Steiger were all considered for the role of Michael Corleone. Hoffman and Nicholson were both offered the part but turned it down.

Sonny Corleone (James Caan in The Godfather, 1972)

Who he is: The older brother who puts a loveable spin on the hot-tempered loose cannon. A man quick to lose his composure, Sonny will do anything to protect his family.

Why he’s the best: His aw shucks, boys will be boys-style charm, ensures that he can get away with just about anything.

Loses points for: Getting fucked over by Carlo of all people.

Memorable quote: “I don’t want my brother coming out of that toilet with just his dick in his hands, alright?”

Best threat: “You touch my sister again, I’ll kill you.”

Useless trivia: Apparently James Caan and Gianni Russo (Carlo) did not care for each other. While filming a fight scene Caan broke two of Russo’s ribs and chipped his elbow. Method actors…

Tony Montana (Al Pacino in Scarface, 1983)

Who he is: A wide-eyed Cuban refugee who becomes a paranoid, AK47-wielding drug kingpin.

Why he’s the best: Tony wants money and power, and is willing to sell his soul to the highest bidder in order to get it. That and the sweet suits.

Loses points for: The Hawaiian shirts.

Memorable quote: “All I have in this world is my balls and my word and I don’t break ‘em for no one.”

Best threat: “You wanna fuck with me? Okay. You wanna play rough? Okay. Say ‘ello to my little friend!”

Useless Trivia: Scarface was given an X rating by the MPAA three times before DePalma and a panel of experts convinced them that it was an accurate portrayal of life in the gritty underworld of drugs. They finally agreed to allow the third version, but DePalma, figuring they wouldn’t remember which was which, released the first, most violent cut of the film.

Henry Hill (Ray Liotta in Goodfellas, 1990)

Who he is: Wannabe made man turned gutless mob rat.

Why he’s the best: Throws absolutely everybody under the bus in order to save himself.

Loses points for: Losing it all because of the drugs. Sorry sap.

Memorable quotes: “As far back as I can remember, I always wanted to be a gangster.”

Best threat: “I swear to my fucking mother, if you touch her again, YOU’RE DEAD”

Useless Trivia: The real Henry Hill got kicked out of the witness Protection Program because after the success of the film he ran around telling anyone who would listen who he was. The government was less than impressed.

Nicky Santoro (Joe Pesci in Casino, 1995)

Who he is: A pint-sized, belligerent sidekick with a short fuse and a poor sense of humor. (Not to be confused with Goodfellas’ Tommy DeVito, who is essentially the exact same character.)

Why he’s the best: Leaning ever-so-slightly towards the explosive end of the gangster spectrum, he stabs a guy in the neck with a pen due to a minor insult.

Loses points for: Briefly falling for Ginger. That really didn’t help matters.

Memorable quote: “Charlie M? You made me pop your fuckin’ eye out of your head to protect that piece of shit? Charlie M? You dumb motherfucker!”

Best threat: “I got your head in a fuckin’ vise. I’ll squash your head like a fuckin’ grapefruit if you don’t give me a name. Don’t make me have to do this, please. Don’t make me be a bad guy.”

Useless trivia: Casino holds the Guiness world record for the most swearing in a movie. The word “Fuck” is used 422 times, most of the time by Pesci.