25 Mobsters In Entertainment We Really Like But Shouldn’t

Posted by , Updated on October 31, 2022

There’s no doubt that gangsters and mobsters are some of the most dangerous and cruel people out there and it’s a safe bet that not many decent people would look up to them in real life. Despite this fact, it’s really weird but also quite true that for some reason many TV and film gangsters, hit men, mobsters, and criminals have become some of the most iconic and admired characters in film history. Here are 25 such “heroes” who have become some of our favorite TV and movie characters for one reason or another. I guess we can’t help but like these mobsters in entertainment…guilty pleasure maybe?


Frank Costello – The Departed

Frank Costello – The Departed

To be honest there is nothing that special about Frank Costello in The Departed except the “rats’’ scene of course, but the fact that Jack Nicholson finally portrays a gangster is enough for us to include Costello on our list. We just loved it.


Lucky Luciano – Hoodlum

Lucky Luciano – Hoodlum

Hoodlum is a fictional story that includes the names of many legendary gangsters. The story takes us back to 1930s Harlem where African-American gangsters struggle for dominion and power against Dutch Schultz who is trying to invade their territory. However, it’s another man who steals the show here, Lucky Luciano, and truth be told, being Italian gives you the clear edge to play in gangster films. What can we say? It’s a matter of being true to life.


Brick Top – Snatch

Brick Top – Snatch

I think we all (or most of us, anyway) agree by now that Guy Richie has managed to take the whole crime and Mafia genre to another level in the past two decades with films such as Snatch, RocknRolla, and Lock, Stock and Two Smoking Barrels. Brick Top is one of the many epic roles Guy Richie “invented” in his films to portray a powerful crime lord who controls and fixes illegal boxing bouts in London and loves to feed the victims of his violent crimes to pigs. How could someone be so cruel, sadistic, and at the same time hilarious? Only Guy Richie has the answer.


Pippi De Lena – The Last Don

Pippi De Lena – The Last Don

Before The Sopranos and James Gandolfini there was The Last Don and Joe Mantegna. All right, all right, maybe the comparison is a bit off but still this superb TV miniseries from the ‘90s is classic material when it comes to Mafia-themed shows and Joe Mantegna as Pippi De Lena was pretty awesome.


Benjamin “Lefty” Ruggiero – Donnie Brasco

Benjamin “Lefty” Ruggiero

“Lefty,” as Benjamin Ruggiero was known to Mafia circles, was a real person and a soldier in the Bonanno crime family. The masses got introduced to him, however, in the film Donnie Brasco where the mighty Al Pacino portrays “Lefty” in a way that makes him look more like a victim when in reality Ruggiero was responsible for the death of twenty-six people.


Sal “Big Pussy” Bonpensiero – The Sopranos

Sal “Big Pussy” Bonpensiero – The Sopranos

Joe Montana had Jerry Rice; Dean Martin had Jerry Lewis; Paul Simon had Art Garfunkel; and Tony Soprano would never be who he was if he didn’t have Sal “Big Pussy” Bonpensiero to look after him. Some things just go together.


Frankie – The Business

Frankie – The Business

This low-budget but unexpectedly good British gangster flick by Nick Love introduces us to Frankie (portrayed by the amazing Danny Dyer) and takes place in sunny Spain in the ‘80s. This totally amateur wannabe gangster, who sounds more like your typical British football hooligan than anything else, dresses like a tennis star of the era, drives his boss’s expensive luxury car, and does all the little errands in order to rise in the ranks. We liked him from the first time we watched the film simply because this boy is all a gangster should never be.


Mr. Blonde – Reservoir Dogs


Reservoir Dogs was one of the early and more awesome works of Quentin Tarantino when the famous director gave to the world many legendary characters without even trying as hard as he’s been trying recently. Even though we could easily select any gangster from this brilliant film we’re gonna stick with sadistic psychopath Mr. Blonde (portrayed by Michael Madsen) simply because we recently discovered that he was the brother of Vincent Vega (John Travolta) from Pulp Fiction which followed shortly after Reservoir Dogs. Be honest, did you know that? We sure didn’t.


Sonny LoSpecchio – A Bronx Tale

Sonny LoSpecchio – A Bronx Tale

Sonny LoSpecchio is a character in 1993’s A Bronx Tale, which was directed by Robert De Niro, and was interpreted as the autobiographical story of the legendary Italian-American actor. As for Sonny? He’s doubtless one of the coolest and best-dressed gangsters in film and even though he wasn’t Calogero’s father, he’s the one who’s remembered as the caring father figure in the film.


Big Chris – Lock, Stock and Two Smoking Barrels

Big Chris – Lock Stock and Two Smoking Barrels

After a lifetime of hits, gang brawls, and petty thefts Big Chris gets “promoted” and is commissioned to go on a special assignment to find four gangster wannabes. Guy Richie once again pleasantly surprises us by hiring a retired footballer and certified badass, Vinnie Jones, who in his film debut is so good and convincing to the point that his character, Big Chris, is now considered an icon among crime/gangster film fans, especially in the UK.


George Jung – Blow

George Jung – Blow

The real George Jung, whom Johnny Depp portrayed so accurately in Blow, was released from prison on June 2, 2014, after serving nearly twenty years for drug smuggling. As the movie clearly shows, Jung was a major player in the cocaine trade in the United States during the 1970s, and we must admit that never again has a gangster’s lifestyle resembled a rock star’s so much in both film and real life.


Jacques Mesrine – L’instinct de mort

Jacques Mesrine – L’instinct de mort

If you’re familiar with French cinema or twentieth century French history then there’s a good chance you know about the notorious gangster Jacques Mesrine. The man who escaped from prison more times than Houdini escaped from a straitjacket wrapped in chains was responsible for numerous murders, bank robberies, burglaries, and kidnappings in France and Canada where he was considered both countries’ number one public enemy. A pair of French films came out in 2008 based on Mesrine’s life in which he was portrayed by the awesome Vincent Cassel, you know Monica Bellucci’s ex-husband.


Léon – Léon: The Professional


Technically Léon isn’t a mobster or gangster but a hit man who works for the mob and has some standards that he never breaks such as killing women or kids, for example. Léon: The Professional is Luc Besson’s best film to date, Jean Reno’s most memorable role, and Gary Oldman as a corrupt cop steals the show. Additionally, we are introduced to Mathilda (played by a twelve-year-old Natalia Portman) who helps Léon open his heart to love again.


Johnny Quid – RocknRolla


We’ve said it a couple of times already on this list but we will say it again—only Guy Richie can come up with characters like this for some reason, and with Johnny Quid he probably shocked even himself. Johnny Quid is an underground musician who tries to make it big and a junkie who fakes his own death so he can help his music sales. Now some of you might wonder what this junkie and rock-star wannabe has to do with the mob, right? Well, Lenny Cole, the head mobster of London’s declining old-school mob, is Johnny’s stepfather and that makes him the only legit heir to Cole’s vast “legacy” in the world of crime. It’s time for Johnny Quid to become a real “RocknRolla.”


John Dillinger – Public Enemies

John Dillinger – Public Enemies

John Herbert Dillinger was an American gangster and bank robber during the Depression and it is estimated that the gang he was leading robbed over two-dozen banks and four police stations. There have been several films made about his story, but in our opinion none was as good as Michael Mann’s Public Enemies with the one and only Johnny Depp in the role of the legendary gangster.


Carlito – Carlito’s Way


Carlito Brigante is a Puerto Rican ex-convict trying to make a decent living and stay out of trouble but a series of unfortunate circumstances and a bad social environment won’t let him do the right thing. Al Pacino takes the role to another level and portrays him as only he could—as one of the most sympathetic, charming, and humane gangsters in film history.


Tommy DeVito – Goodfellas

Tommy DeVito – Goodfellas

The most fascinating part of Tommy DeVito’s story—a role based on a gangster named Thomas Anthony “Two-Gun Tommy” DeSimone—is that Joe Pesci did not physically resemble the tall, muscular “Two-Gun Tommy” at all, who was only in his teens and twenties during the events depicted in Goodfellas. However, Pesci’s portrayal was between 90 and 95 percent accurate according to police reports and that should tell you something about Joe’s incredible acting skills, which certainly make up for his small stature.


Vincent Vega – Pulp Fiction

Vincent Vega

Vincent Vega is not just another mobster but the role that resurrected John Travolta’s career and gave him an Academy Award nomination. Vincent is a hit man working for mob boss Marsellus Wallace (Ving Rhames) and looks-wise he resembles more a rockabilly music star a la Elvis than your typical Mafia man. Last but not least, he’s easily the greatest dancer-gangster in film history and his iconic dancing scene with Mia Wallace (Uma Thurman) is clear proof of this.


Fat Tony – The Simpsons

Fat Tony – The Simpsons

Some of you might complain about this one being just an animated character but then again so what? Marion Anthony “Fat Tony” D’Amico is a gangster and the underboss of the Springfield Mafia and we were first introduced to him in the third season of The Simpsons. He is voiced by Joe Mantegna and there’s no doubt that this character has made gangsters look and sound cool even in the world of animation.


Nikolai – Eastern Promises

Nikolai – Eastern Promises

Eastern Europeans have this “magic” thing going on about them when it comes to badass and tough “jobs.” They have proved that historically in war and more recently in combat sports such as boxing, MMA, and wrestling that once they started participating professionally they literally changed the face of these sports. Same goes with the Mafia we’re afraid; once the Russian Mafia got into the “game” the Italians started to look kind of soft really. Nikolai in Eastern Promises is the perfect example of a Russian Mafia character and if you have seen the film then you definitely know what I am talking about.


Michael Corleone – The Godfather


Michael Corleone is the main character of The Godfather trilogy, portrayed by the legendary Al Pacino, who was twice nominated for an Academy Award for his portrayal but unfortunately never won. This role has been named the eleventh most iconic villain in film history by the American Film Institute but we’re pretty sure that he ranks even higher in the hearts of the movie’s fans.


Keyser Söze – The Usual Suspects


Keyser Söze is probably the most mysterious, vicious, supernatural, and dark mobster in film history, at least according to his self-description or, to be more accurate, as described by his alter ego, Roger “Verbal” Kint. After all these years we’re still trying to figure out if he was a man or the devil himself. “And just like that . . . he’s gone.”


Tony Soprano – The Sopranos

Tony Soprano – The Sopranos

Tony Soprano is without doubt the most famous and charismatic TV mobster in history and this role in the outrageously popular HBO drama The Sopranos made James Gandolfini one of the highest-earning and most awarded TV actors (for one role) ever but unfortunately he left us too soon.


 Tony Montana – Scarface


Tony Montana is legally to blame for possibly the most famous quote in the history of any gangster and Mafia film ever made, and of course I am referring to the epic “Say hello to my little friend!” Tony Montana (portrayed so convincingly by Al Pacino) has become a pop culture icon and is one of the most recognizable movie characters of all time, and in 2006 a video game called Scarface: The World Is Yours was developed by Radical Entertainment and published by Sierra Entertainment in honor of the film.


Vito Corleone – The Godfather

Vito Corleone – The Godfather

Vito Corleone is another character from Mario Puzo’s novel The Godfather and its film adaptation. The role has been portrayed by Robert De Niro (as a younger man) and the one and only Marlon Brando in the first film of the trilogy. Premiere magazine named Vito Corleone the greatest movie character in history and I don’t think many can disagree with that.

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