We’ve already covered some of the best crime movies ever made, but what about the individual gangsters who made those movies so great? We wanted to go back and take a look at some of the performances that defined those iconic gangster films, and see if we couldn’t isolate the 10 best gangsters in movie history and take a peek at what makes these violent, psychopathic criminals so compelling. Steeped in violence, crime, and profanity, many of the individuals portrayed here are downright despicable folks; so why can’t we turn off the television when they’re on the screen? That’s what we want to talk about today, and that’s what we want to hear from our readers about. Which one of these famous performances is your favorite, and why? Sound off in our comments section and let us know which gangster you’d root for in a shootout of epic proportions.
10. Bullet Tooth Tony (Snatch)
Guy Ritchie films are a gold mine for lists like this, as his movies tend to focus on the criminal underworld of the United Kingdom and feature a wide array of intriguing characters, not the least of which is Bullet Tooth Tony, the smarmy and intimidating enforcer portrayed by Vinnie Jones in Snatch. A big, nasty man with an even bigger and nastier gun (a Desert Eagle, .50 to be exact), Bullet Tooth Tony is an expert in intimidation, retrieval and enforcement services, a set of skills which make him very valuable to the higher ups of London’s seedy sects; when he’s called upon to do a job, Bullet Tooth Tony gets it done, as we see numerous times over the course of the film. Ritchie, who always pairs his violence with a wry sense of humor, imbues Bullet Tooth Tony with a levity that makes it almost amusing to watch him slam a car door on a man’s head. Funny how that works, eh?
9. Jules & Vincent (Pulp Fiction)
Alright, so it’s technically the eleven greatest gangsters in the history of cinema, but are you really going to hold Jules and Vincent against us? Have there ever been a more iconic pairing of gangsters? We just couldn’t leave them out, and their casual bickering and conversation while engaging in horrendous acts of the criminal nature is part of what makes Quentin Tarantino’s Pulp Fiction the compelling masterpiece that it is. Jules and Vincent, who are technically hitmen working for the gangster Marsellus Wallace (which, we think, makes them sort of gangsters by proxy) are smooth talking characters who are quick with the trigger finger, a character trait that finds them in some hot water after poor old Marvin ends up hitching a ride in the backseat (spoiler alert, Marvin doesn’t make it out of the film alive). Jules and Vincent, who are portrayed by Samuel L. Jackson and John Travolta, respectively, earn a role on this list due to their excellent chemistry and criminal proclivities.
8. Stansfield (Leon: The Professional)
Who’s to say corrupt cops can’t be gangsters too? If anyone were to argue with us on that point, we’d refer them to Luc Besson’s Leon: The Professional, which features one of the most terrifying gangsters ever put to film in Gary Oldman’s Stansfield. A corrupt police detective with a fondness for classical music and killings sprees, Stansfield is a maniac who has his eye on Natalie Portman’s character, Matilda, after she escapes from him while he’s murdering her family. An underrated film that features dynamite performances from Portman, Jean Reno (in the lead role) and most importantly Oldman, Leon: The Professional undoubtedly features one of the greatest movie gangsters of all time in Stansfield, whose visibly restrained demeanor still gives us the heebie jeebies. Oldman, who is a master of the performing arts and excels when playing a villain, is gleefully unhinged here, and if you haven’t already checked out this excellent movie released in 1994, we’d recommend you do it immediately.
7. Don Logan (Sexy Beast)
Ben Kinglsey doesn’t get as much credit as he’s due, especially in the last little while (to be fair, his choice in films during this time has been…let’s say, less than stellar). One of the greatest actors of his generation, Kingsley has shown time and time again that he’s able to commit fully to a role, whether that role is of a peaceful nature (like when he played Ghandi), or a role of the more violent persuasion, like his portrayal of Don Logan in Jonathon Glazer’s Sexy Beast. The story of a safe cracker (the normally intimidating Ray Winstone) drawn out of retirement when his nemesis, Logan, appears and coerces him into one last job, Sexy Beast sees Kingsley playing Logan with a sort of childish impatience, and the result is a hilarious mix of violent criminal and petulant youth that rates as one of the more intriguing gangster performances we’ve ever seen on screen.
6. Frank Costello (The Departed)
It should come as little surprise that many of the affectations and mannerisms of Frank Costello, the deranged criminal overlord from Martin Scorsese’s The Departed, were added at the suggestion of Jack Nicholson, who played the volatile character with a sort of crazed intensity that he seems able to bestow on most all of his performances. Nicholson, who has never been more at home than when playing unstable characters, shines as Costello, and his presence in the film adds a level of authenticity to an altogether exceptional tale of the criminal underworld. The Departed, which remains one of the more acclaimed films on this list (it’s the film that finally won Martin Scorsese his elusive Best Picture Oscar), is at its best when pitting Nicholson’s Costello against the leaky machinations of his criminal underlings, as he attempts blindly to find the informant hidden in his crew.
5. Al Capone (The Untouchables)
The old adage that art imitates life is most especially true at the movies, where audiences gravitate towards stories based on historical events. Time and time again we’ve seen Hollywood take a familiar story from the history books and re-purpose it for entertainment, and oftentimes this marriage of fact and fiction results in a more compelling story than either could tell alone. As such, it’s little wonder that The Untouchables, the Brian De Palma-directed story of Elliot Ness and his crew of law enforcers tasked with stopping Al Capone (as played by Robert De Niro), provides us with a wildly engaging portrayal of a gangster in Capone, the real life criminal who made a fortune running booze during the Prohibition era. In De Niro’s hands, Capone is a stylish and understated gangster who isn’t afraid to talk pretty or get ugly, and his propensity for the shootout helps make The Untouchables an electrifying ride that is frequently underrated among crime film aficionados.
4. John Dillinger (Public Enemies)
Say what you will about Michael Mann’s Public Enemies (namely that it wasn’t a very good movie), but Johnny Depp’s version of notorious real life bank robber John Dillinger was spot on. In Depp’s hands, Dillinger is a charming, dangerous and calculating gangster with an affinity for taking money from whatever bank he wants, whenever he wants. Public Enemies, which was released to lukewarm reviews despite Depp’s strong lead performance, never truly lived up to the potential of its historical narrative and excellent cast, which also included Marion Cotillard, Christian Bale and Billy Crudup. Regardless of how you feel about the film, it’s a pleasure to watch Depp in a role devoid of camp or absurdity, and Public Enemies offers a glimpse of just how good Depp can be when he isn’t slathered in makeup and gallivanting around a Tim Burton set.
3. Tony Montana (Scarface)
We’re well aware that Scarface isn’t the greatest gangster film of all time. Brian De Palma’s ultra-violent film is too long for our tastes, and features some elements and scenes we aren’t particularly fond of. That said, it undoubtedly features one of the greatest gangster performances of all time, as Al Pacino’s portrayal of Cuban immigrant turned drug kingpin Tony Montana has become as inseparable from the crime genre as a performance could be. In Pacino’s hands, Montana does disservice to the word “volatile,” as his unpredictable and psychotic behavior gives audiences an accurate portrayal of a man lost to the forces of violence, terror, drugs and power. It’s an infinitely compelling performance that shines through in even the most gruesome of Scarface‘s scenes, and this masterful portrayal is part of the reason why De Palma’s film has gained more critical favor in the years since its release.
2. Tommy DeVito (Goodfellas)
Henry Hill (Ray Liotta) may be the main character of Martin Scorsese’s masterpiece Goodfellas, but it’s Tommy DeVito, as portrayed by Joe Pesci, who rates as the most iconic gangster in the definitive film about gangsters. Goodfellas, which tells the story of Hill’s involvement with the Lucchese crime family through their rise and fall, remains one of the most cited examples of excellence in the crime film genre, and Pesci’s iconic performance as Tommy DeVito, the nasal-voiced, fast talking, violent enforcer for the Luchesse family, is ranked number two on this list for a reason. Equal parts hilarious and insane, DeVito is the quintessential wiseguy, and Pesci was rewarded for his dominating performance with an Academy Award for Best Supporting Actor.
1. Vito Corleone (The Godfather)
Could anyone but Brando have topped this list? We gave Pesci a good hard look, but in the end we decided having anyone but Vito Corleone atop a list of the greatest gangsters in movie history would be a sham. An iconic performance that’s only grown in legend since The Godfather was released in 1972, Marlon Brando’s Vito Corleone is the soft-spoken patriarch of the Corleone crime family, and his understated yet intimidating performance has ensured viewers are rapt while watching this now-legendary film. Brando’s performance as Corleone, now one of the most acclaimed in the history of cinema, almost didn’t happen; in fact, Ernst Borgnine was the studio choice for the role, but director Francis Ford Coppola went to bat for Brando, suggesting the actor was the only one who could truly portray the criminal overlord as he needed to played. Turns out, the director knew best.