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Power Ranking The Coolest and Toughest On-Screen Mob Bosses

Power ranking the five of the coolest and toughest mob bosses from popular movies and TV shows.
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Best Mob Bosses TV Movies

Photo: Comcast Corporation

March 24th marks the anniversary of the theatrical release of The Godfather (1972). To celebrate, we are running down our list of the top mob bosses from TV and film.

We are focused on fictional characters for this list, so real-life mobsters seen on-screen will be omitted (I might break that rule FYI). We are also narrowing in on what we refer to colloquially as the mob, so other gang leaders will not be considered.

Honorable Mentions

Sonny: A Bronx Tale (1993)

Sonny was the type of leader you'd love to have. Tough when he has to be, but compassionate about his people. He gave life advice to young Calogero that all of us carry around to this day.

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Jimmy Conway: Goodfellas (1990)

Jimmy is cool and tough, no doubt about it, but he's not really a boss, to be honest. He leads the crew throughout the film, but they are pretty low-level. Near the end, Tommy is taken for his ceremony to become a made man, he would have been Jimmy's boss. That is Chris Moltisanti before Season 3 status for those keeping score, and it keeps Jimmy on the bench for me.

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Fat Tony: The Simpsons (1991- )

He's a timeless mobster and deserves to be mentioned here. You can't pull off a scheme in any of the boroughs of Springfield without Fat Tony getting his taste.

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Alphonse 'Big Boy' Caprice: Dick Tracy (1990)

He was everything a good mob boss should be. Everyone knows he's the boss, and no one can prove anything. Don't sleep on Dick Tracy, folks.

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Now, on to our list!

5) Don Vito Corleone: The Godfather (1972)

Only No. 5? Imma be sleeping with the fishes fa sho. Don Vito belongs on this list, no doubt about it. But, we hear more of his lore in the first movie, less action.

He insists on Michael having no part of the family in the family business, despite his youngest son's proclivity to replicating his father's success, and refuses to even consider entering the drug game despite the abundant money waiting to be made.

Did I just dock Don Vito points for being a caring father and conscious of the impact on his community Sure did, I'm not hiring the principal for my kid's school here.

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4) Frank Costello: The Departed (2006)

Frank was a man with a plan. Having the forethought to get his own man in the police from the jump is the definition of cool and tough.

Plus, unlike pick No. 5, Frank let money talk. Sell off microprocessors to the Chinese to make a quick buck? You betcha. The fact he's also an informant is pretty savage.

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RELATED: The Absolute Best 5 Lines From The Departed

3) Bill the Butcher: Gangs of New York (2002)

This is an instance of me sort of breaking my own parameters as a) Bill is based on a real person (loosely) and b) is he really a "mob" boss? I'm declaring that he is. It's a Martin Scorsese movie, so it counts.

I like Bill because he's not afraid to get his hands dirty. Very dirty. An expert with a blade or cleaver in his hand, he can stick you without you noticing or hit you in a weak spot from across a room with a deft throw. He was the man, and he made sure everyone knew it.

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2) Tony Soprano: The Sopranos (1999-2007)

Deciding No. 1 and No. 2 was by far the toughest task in compiling this list. Both were brilliant, vicious, and had the semblance of being a family man.

In the end, I decided it was Tony Soprano's vices that would put him in line for the silver medal (RIP 2020 Tokyo Games). Tony was WAY too prone to thinking with his little head rather than the big one, and it put his crew, his family, and himself in precarious situations on the regular. He'd get wasted and hop in his truck and just hope his antidepressants didn't kick in.

All that aside, he was the man. When the heat was on, he got everyone to buy into the notion that he wasn't actually the boss, and the deflection 1,000% worked. Tony was a masterful tactician, seeking out strategies through Sun Tzu's Art of War. He bested those who crossed him pending the results of a certain diner scene. Do I think he survived? I won't stop believing that he did.

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1) Michael Corleone: The Godfather (1972), The Godfather:Part II (1974)

Our top pick showed ruthless cunning and an ability to sniff out the truth. Cross Michael Corleone at your own peril.

In the first movie, he transforms from a military man who's aware of the family business, to THE GODFATHER by the end. He arranged mass hits that Jack and boys would have only dreamed of on Breaking Bad.

Michael kept that separation of church and state with Kate and his kids, but they knew, though just never enough for it to backfire on him. The revenge he enacts on Fredo in Part II is gut-wrenching.

The Godfather: Part III (1990) isn't as bad as a lot of people make it out to be, but I don't need it to put Michael in my top spot.

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