Idiots Guide: 12 Best Gangsters in Film History

Every good movie needs a good villain, but what happens when the entire movie is about villains? Awesome is what happens! Especially, if you’re the kind of movie fan who has a tendency to root for the bad guy. The kids in film school used to call them ‘Anti-Heroes’ these days however, we like to call them exactly what they are…’Bad-Ass Mothers’. Some of these characters have variations of complex inner emotional turmoil that they deal with through violence, some have personal demons they are exercising, but they all have something about them that in some unique way, audiences identify with. That something is decided on an individual basis, depending on an individuals personal level of catharsis. Idiots Guide presents a thoughtful list of 12 of the best gangster characters in film history.


#12.  Robert De Niro  /    “Neil McCauley”   /   Heat    (1995)  


A professional thief is what Neil McCauley did for a living, the illegality of which was compounded by the murders he sometimes had to commit in order to successfully complete the job. He lived a solitary life with a mantra that stated “Don’t ever let yourself get attached to anything you are not willing to walk out on in 30 seconds flat if you feel the heat around the corner.” What a cowboy, right?  De Niro was masterful in Michael Mann’s ‘Heat’ (1995). Added bonus? Arguably the best shootout scene (Downtown Los Angeles) in film history.

#11.  Johnny Depp   /   “James ‘Whitey’ Bulger”  /   Black Mass  (2015) 

Johnny-Depp Black-Mass

It couldn’t have been easy for Johnny Depp to play a man who many consider to be a model of evil. Whitey Bulger was certainly on the short list of candidates for the devil incarnate during his hey day ruling the South Boston underworld. His menace was if nothing else, diabolical to the point that a movie about his life of crime was green lit. A compelling drama for audiences, a tragic outcome for his many victims.

#10.  Vinnie Jones  /   “Big Chris”  /   Lock, Stock and Two Smoking Barrels   (1998) 

Vinnie Jones

Lock, Stock and Two Smoking Barrels introduced Vinnie Jones to worldwide audiences…as an actor. The former Chelsea footballer was cast as ‘Big Chris’ in Guy Ritchie’s hit film. Jones played a likable, albeit ultra violent debt collector thug and played it magnificently. His imposing ‘tough guy’ image has served him quite well.

#9.  Michael Madsen /   “Mr. Blonde”  /   Reservoir Dogs   (1992)  

Michael Madsen 3

Simply put, Michael Madsen’s ‘Mr. Blonde’ was the sadistic psychopath dog of the pack in Director Quentin Tarantino’s classic heist picture ‘ Reservoir Dogs’ (1992). How sadistic you ask? Here’s an insightful quote that sums it up “Listen kid, I’m not gonna bullshit you, all right? I don’t give a good fuck what you know, or don’t know, but I’m gonna torture you anyway, regardless. Not to get information. It’s amusing to me, to torture a cop.” – Mr. Blonde.  Any questions?

#8.   Ving Rhames   /   “Marsellus Wallace”   /   Pulp Fiction   (1994) 


‘Pulp Fiction’ is an all-time classic film-noir crime drama/ black comedy, if that sounds like a lot then take the title into consideration ‘Pulp’ is by definition an odd mixture. There are great performances throughout Quentin Tarantino’s  3 (+) hour film, not the least of which is Ving Rhames as crime boss ‘Marsellus Wallace’. Fans of this picture will understand what is specifically memorable about this character. Here’s a hint, it isn’t about socio-pathetic murder. Nevertheless, Rhames’s character will always be memorable to fans both old and new. Now, if I can just get the image of that red ball out of my mind…

#7.   Al Pacino  /   “Carlito Brigante”    /  Carlito’s Way   (1993) 

Al pacino carlitos way

Director Brian De Palma’s 1993 release of ‘Carlito’s Way’ included a star studded cast with the likes of Sean Penn, Penelope Ann Miller, Luis Guzman and John Leguizamo doing their part in this classic crime picture. Of course there’s the title character ‘Carlito Brigante’ played flawlessly by acting legend Al Pacino, a man who gets an unlikely second chance at life after being released 5 years into a 30 year prison sentence on a technicality. The problem is of course that he’s finished with the streets, but the streets aren’t finished with him, not by a long shot. Brigante is an old gangster who can’t seem to shake free of the life fast enough to save his own life. A highly compelling drama, a great gangster role.

#6.  Christopher Walken   /  “Don Vincenzo Coccotti” /  True Romance  (1993) 

Christopher Walken True Romance

Fans of  Director Tony Scott’s ‘True Romance’ will remember that Christopher Walken’s ‘Don Vincenzo’ character doesn’t get a ton of actual screen-time, the genius is what transpires during that special time. There is a famous dialogue sequence between Walken and Dennis Hopper that delves into the racial history of Sicily as Hopper tells it, Walken’s reaction to this is the stuff of movie lore. Walken plays this character with a quiet, sinister intensity that would shake the hardest of criminals. Memorable? Definitely, One of the best gangsters in film? Abso-f*cking-lutely.

#5.   Joe Pesci   /   “Tommy DeVito”   /  Goodfellas   (1990) 

Joe Pesci  Goodfellas

“You mean, let me understand this cause, ya know maybe it’s me, I’m a little fucked up maybe, but I’m funny how, I mean funny like I’m a clown, I amuse you? I make you laugh, I’m here to fuckin’ amuse you? What do you mean funny, funny how? What the fuck makes me so fuckin’ funny?” – Tommy DeVito  There’s not a ‘Goodfellas’ fan in the world who doesn’t remember this dialogue exchange between Joe Pesci and Ray Liotta. It’s just one of many memorable parts to one of the greatest gangster roles of all-time.

#4.   Robert De Niro   /  “Al Capone”   /  The Untouchables   (1987)  


Al Capone has been portrayed many times in film history. It’s arguable that Robert DeNiro’s take is the very best of the bunch. He gained the appropriate weight for the role and played it masterfully. Once again Director Brian De Palma helmed a memorable gangster picture, and with the help of DeNiro, it’s an all-time classic, you want to witness a true gangster in action? Watch this.


#3.   Harvey Keitel   /   “Charlie Cappa”   /   Mean Streets  (1973)

Harvey Keitel Mean Streets

In Director Martin Scorsese’s ‘Mean Streets’ you will find the Charlie Cappa character who is a young  and up and coming Italian-American mobster trying to make his bones in the New York Mafia. Harvey Keitel plays this character in virtuoso fashion, dark and brooding.

#2.  Christopher Walken   /  “Frank White”  /  King of New York   (1990)

Christopher Walken King of NY

Abel Ferrara’s ‘King of New York’ is an all-time cult classic gangster film. Christopher Walken’s  ‘Frank White’ is the kind of gangster that is widely idealized in theory but doesn’t exist in the modern world anymore, if ever. Frank White is a modern day gangster with an understated ‘Robin Hood’ quality to his persona. He loves his city and has plans for it’s resurrection. It’s an amazing movie, and an even better performance by Walken. You want to see a real gangster do his thing? Take a look…


#1.   Al Pacino   /  “Tony Montana”  /  Scarface  (1983) 

al pacino scarface

Al Pacino’s ‘Tony Montana’ in ‘Scarface’ (1983) is the hands down best gangster portrayal in movie history. There have been many that have been close, but none as good as this movie, this character and this performance…Not convinced? Take a look.