Top 20 Fictional Mobsters

By Ben on August 31st, 2009

Everyone loves a good mob flick, and over the years, we’ve been treated to many great ones, on both television and at the cinema. Now, it’s one thing to make a movie based on real life events, as we’ve seen in Goodfellas, Donnie Brasco and Casino, but when fiction is involved we often get very memorable characters, some of whom we even look up to despite their criminal nature. So, lets now take a look at the best fictional on-screen gangsters (sorry, no comics).

20. Vincent ‘Vinnie’ Antonelli (My Blue Heaven)

Steve Martin as a gangster? In the Witness Protection Program with Rick Moranis? Sold. And to think that Arnold Schwarzenegger was offered the role but opted to film Kindergarten Cop instead.

19. Tommy Vercetti (Grand Theft Auto: Vice City)

Voiced by Ray Liotta, who is best known for playing Henry Hill in Goodfellas, Vercetti is similar to Tony Montana in Scarface, as is the game. He’ll serve as the lone video game character to make this list, representing the entire GTA franchise.

18. Fat Tony (The Simpsons)

The local mob boss on The Simpsons is voiced by Joe Mantegna and isn’t overused like some of the other characters. It’s always hilarious when Homer and Krusty get in trouble with him.

17. Alphonse “Big Boy'” Caprice (Dick Tracy)

To me, this is the most underrated Al Pacino role, because he wasn’t just standing around doing his ho-ah! thing but instead putting his spin on a comic book character. Big Boy is far more entertaining than Michael Corleone.

16. Paul Vitti (Analyze This)

Come on now, you like this movie and you know it. Bob De Niro as a mob boss who sees a psychiatrist? Brilliantly funny.

15. Jabba the Hutt (Star Wars)

Jabba had it all. A palace, dancing girls with tentacles coming out of their heads, a space monkey, a Rancor, and his enemies in carbonate. I’m sure John Gotti was drooling with envy when he saw that.

14. Antonio “Nino” Schibetta (Oz)

Fans of HBO’s Oz will appreciate this pick. He wasn’t around long (he was offed in Season One after eating a salad tainted with broken glass), but he proved to be the most respected and powerful boss behind bars at Oswald State Correctional Facility. His son, Peter, didn’t fare so well.

13. Frank Booth (Blue Velvet)

Dennis Hopper expertly plays a sick, twisted sadist and the central figure in the underworld of drugs and prostitution in David Lynch’s psychological thriller.

12. Vincenzo “Vincent” Coccotti (True Romance)

In a film known for its ensemble cast, Christopher Walken gets to play the best part, a sadistic mobster kingpin who enjoys intense psychological torture sessions with those who don’t cooperate with him.

11. Brick Top (Snatch)

Alan Ford plays a psychotic gangster in Guy Ritchie’s 2000 film set in the London criminal underworld.

10. Wong Hoi (The Killer) and Uncle Hoi (Hard Boiled)

To represent the Chinese Triads, on this list, we’ll go with a pair of characters from John Woo’s classics, The Killer, and Hard Boiled. Both were powerful figures in their respective films, but ultimately both died.

9. Sonny LoSpecchio (A Bronx Tale)

At first I wasn’t a huge fan of this film because it didn’t seem to add much to the mob movie genre, but the more I watched it the more it grew on me, mainly because of Chazz Palminteri. Watch the scene below. Could you picture this happening with the guys from The Godfather?

8. Don Logan (Sexy Beast)

Ben Kingsley says he based his performance largely on his grandmother, whom he called “A vile and extremely unpleasant woman.” Logan, a violent sociopath, is a recruiter for the London underworld, who puts people together into teams to pull off various heists.

7. Marsellus Wallace (Pulp Fiction)

“Does Marsellus Wallace look like a bitch?” Jules (Samuel L. Jackson) asks some drug dealers in an apartment. And we find out later, he is. Despite that scene, Ving Rhames steals the show as Wallace in Pulp Fiction. This is one boss who isn’t afraid to get dirt under the fingernails. Could you imagine Vito Corleone chasing Bruce Willis into a pawn shop before being held up by rednecks then getting raped? What kind of speech would Vito make after-the-fact? Here’s how Wallace does it:

6. Keyser Söze (The Usual Suspects)

Yeah, it’s Kevin Spacey, who isn’t exactly Robert De Nero or Al Pacino, which is why I was hesitant to even put him on this list. But The Usual Suspects is so well written that ultimately Spacey is the best bad guy on here because of how he gets away with it. See if Jabba the Hutt can pull this off.

5. Tony Montana (Scarface)

I always found Al Pacino in this role to be more comical than serious, particularly with that catch phrase, but the film is serious and it’s carved out a role in pop culture so here he is.

4. Francis “Frank” Costello (The Departed)

The character that Jack Nicholson plays shares the same name as a legendary mobster named Frank Costello, but is actually loosely based on James “Whitey” Bulger, who has been on the FBI’s Top Ten Fugitive list for the last decade or so.

3. Michael Corleone (The Godfather II)

Because The Godfather and The Godfather Part II are arguably two of the best films ever made, the Corleone family bosses rise to the top of this list, though they clearly don’t have the pizazz as some of the other gangsters. In fact, relatively speaking, they’re boring. But their power is supreme. Michael took a kingdom that his father made out of nothing and turned it into a criminal empire.

2. Anthony “Tony” Soprano (The Sopranos)

Tony Soprano has more screen time than anyone else on this list combined, and therefore rises up the ranks. We know more about Tony than anyone. Sure, he’s only the northern Jersey boss of what the N.Y. families call a ‘glorified crew,’ but that actually made the show even better.