5 Screen Gangsters We All Hate to Love

Let’s face it, we all love bad guys. From Darth Vader to The Joker, a great screen villain stays in the memory long after the credits have finished rolling. In many cases, the villains are more interesting than the hero. It’s been that way since the early days of cinema and it’s highly unlikely that it’ll change any time soon. We all love a villain, whether it’s one we love to hate or one that we hate to love.

The crime and gangster genre has an incredible rogue’s gallery. From The Godfather and other Mafia tales to the grim London streets of Guy Ritchie’s Lock Stock and Two Smoking Barrels, there is a never-ending roll sheet of great roles that has featured on our screens for decades. Here are 5 screen gangsters you can’t help but fall in love with, despite the many reasons why you shouldn’t…

Tommy DeVito from Goodfellas (1990)

Don’t ever tell him that he’s funny…

Goodfellas is a wonderful film that features amazing characters from one-scene players to top billing, where Robert De Niro, Ray Liotta and Joe Pesci are seated. Pesci especially is at his very best here, and is absolutely terrifying as volatile gangster Tommy DeVito. When you’re watching the film on TV he is a joy to watch, hilarious and completely unpredictable, with many great scenes. But in the film itself, he is your worst nightmare, with the ability to go from telling jokes to beating a man to death with his bare hands in a matter of seconds. Just watch the scene in the private bar when local kid Spider sticks up for himself. It’s one of the most heart-breaking scenes in cinema. But the “funny how?” scene takes the cake. You can hear the colour fading from Ray Liotta’s face as his character Henry Hill is intimidated and humiliated in equal measure when he tells Tommy he’s a funny guy.

Most. Awkward. And. Terrifying. Scene. Ever.

Frank Nitti from The Untouchables (1987)

Don’t answer your door to him…

The right-hand men are always the best villains. Darth Vader (and Darth Maul) from Star Wars to Mr Joshua from Lethal Weapon and Karl from Die Hard, every big bad should have a charismatic sidekick to steal the movie from under them and give the good guys absolute hell until they are killed in a very, very cool way.

Frank Nitti is by far the most riveting presence and interesting character in The Untouchables. Wearing a sharp white suit and killing good guys with pinpoint accuracy either with a tommy gun or handgun, Nitti is completely awesome at being a horrible piece of work. You almost forget that Robert De Niro (who plays gangster boss Al Capone) is even in the film, so great is Nitti. The audience is rewarded for its love by having a moment to cheer about, when our hero Elliot Ness throws him from the roof of a building, sending him crashing through the roof of a car on the Chicago streets below.

Brick Top from Snatch (2000)

Don’t ask him what ‘nemesis’ means…

Snatch is nearly always remembered for Brad Pitt’s hilarious and off the wall performance as Irish traveller and bare knuckle boxer ‘One Punch’ Mickey. But by far the best character in the film is Alan Ford’s absolutely terrifying portrayal of London gangster boss Brick Top, a character so sinister yet hilariously entertaining that all his best lines have been dubbed over Darth Vader’s scenes from Star Wars in a YouTube parody video. The man is a legend. When he isn’t fixing fights and feeding people to pigs, Brick Top likes nothing more than a nice cup of tea. No sugar though. He says he’s sweet enough.

Stringer Bell from The Wire (2004-2008)

Don’t stray from the rules of the game…

When somebody mentions the word “gangster”, you instantly think of a gun toting psychopath in a sharp suit who you definitely don’t want to cross. The Wire’s Stringer Bell completely broke the mould of modern day gangsters and became the #1 target for man crushes everywhere. Simply put, Stringer Bell is the coolest bad guy in the history of TV, maybe even of any medium.

2nd Lieutenant to best friend and drugs baron Avon Barksdale, Stringer Bell is the man with the plan, and the guy who puts that plan into place. Whether it’s getting the package (drugs) out onto the corners or rooting out a snitch in the organisation, Bell orchestrates everything yet keeps his hands almost completely clean. He even goes to college so he can keep his legitimate businesses running properly so the cops can’t expose them as fronts. He doesn’t use a gun in 38 episodes of TV too, something unheard of in the world of gangster.

Ray ‘Bones’ Barboni from Get Shorty (1995)

Don’t call him ‘Barbone’…

Ray ‘Bones’ is a gangster with a temper as fiery as the Miami heat, and he throws put-downs and f-bombs around like a heavyweight boxer throws punches. When John Travolta’s character Chili Palmer breaks Barboni’s nose but then ends up having to working for him, you know that there’s going to be carnage, as Barboni aims to get the one-upmanship by any means necessary, and most of those means involves shooting people and punching women in the face. He sounds delightful, right?

No, he’s horrible, but actor Dennis Farina makes you love to hate him. He is absolutely hilarious, and you will him to meet his comeuppance every time he’s on the screen. But when he’s delivering one-liners as good as this, it’s hard not to love him:

Chili Palmer: How did you get in here?
Ray Bones: It was easy. I told ’em I was you, I acted real stupid and they believed me.

There aren’t many Ray Barboni quotes that don’t include f-bombs, so here is a list of his best quotes to view at your own discretion. Enjoy. Giggle. Salute Mr Barboni.