Greatest Gangster Characters of All Time

These tough guys did more than just steal the loot.

Greatest Gangster Characters of All Time

The gangster genre has captivated audiences since the first pre-Code films hit the silver screen almost a century ago. Even though the definition of being a gangster has changed, our love for movie and TV tough guys has only grown stronger with each passing decade.

A life of crime isn't for most people, but it sure can be fun to watch. These are the best gangster characters of all time.

30. Bandit Who Fires at Camera

Warning: Content contains spoilers.

Movie: The Great Train Robbery

Year they first appeared: 1903

Actor: Justus D. Barnes

Bottom line: This silent film follows an outlaw gang who robs a train and eventually gets caught by a sheriff’s posse. While it wasn’t the first Western film, it was a smash success due to its groundbreaking effects by director Edwin S. Porter.

The close-up of a gang member shooting at the camera was so new to audiences, they were afraid they were being shot. This sequence was the inspiration for "Goodfellas" in its story and its final sequence. Joe Pesci "shoots" the audience much in the same manner.

29. Caesar "Rico" Bandello

Movie: Little Caesar

Year they first appeared: 1931

Actor: Edward G. Robinson

Bottom line: "Little Caesar" tells the story of a small-town criminal, Rico (aka Little Caesar), who ascends the ranks of the mob. While it’s a well-worn trope, it was one of the first gangster films ever made and captivated audiences.

Rico is a ruthless bully, but he’s charismatic, clever and extremely manipulative. Robinson played him so convincingly it made him a bona fide star and created a genre that continues to fascinate us to this day.

28. Tom Powers

Movie: The Public Enemy

Year they first appeared: 1931

Actor: Jimmy Cagney

Bottom line: Rico walked so Tom Powers could run. When "Public Enemy" came out, it was so successful, some theaters showed it on a loop 24 hours a day for several weeks. This is due in large part to Cagney’s magnetic screen presence.

He didn't play the role like a cartoon caricature of a gangster. He used street slang and body language he remembered from organized crime members he saw as a child.

27. Jack Carter

Movie: Get Carter

Year they first appeared: 1971

Actor: Michael Caine

Bottom line: Jack Carter, a gangster from London returns to the small town in England where he was raised after finding out his brother has died under mysterious circumstances.

As he's been on the wrong side of the law for much of his life, he knows something's fishy when he sees it, and investigates, only to find out his brother was murdered by the local mob.

"Get Carter" paints a grim picture of the seedy underbelly of working-class England in the 1970s. While it first opened to mixed reviews, it has since won critical acclaim and has been cited as an influence by Quentin Tarantino and Guy Ritchie.

26. Tony Montana

Movie: Scarface

Year they first appeared: 1983

Actor: Al Pacino

Bottom line: Cuban refugee Tony Montana is a man with no prospects and no courage when he arrives on American shores in 1981. But he pretends he has both (with the help of a mountain of cocaine) and moves up the ranks to be a high-powered crime boss in Miami.

Al Pacino’s bombastic performance as Tony Montana is the stuff of a thousand memes. Think about it. How many times have you heard "Say hello to my little friend"?

25. Marsellus Wallace

Movie: Pulp Fiction

Year they first appeared: 1994

Actor: Ving Rhames

Bottom line: A Los Angeles strip club owner and high-powered gangster, Marsellus is brutal and controlling (as most people in his line of work tend to be), but he carries himself with a quiet confidence and charm, even in the most unexpected situations.

Those who cross him live to regret it. However, when he meets his match in Bruce Coolidge, a boxer who betrays him but comes to his aid when he needs it the most, he shows unexpected fairness and empathy, allowing Bruce to leave town with his pride and limbs intact.

24. Chalky White

TV series: Boardwalk Empire

Year they first appeared: 2010

Actor: Michael K. Williams

Bottom line: Chalky White is a shrewd, tough and extremely powerful racketeer operating out of Atlantic City during Prohibition. Despite occasional disagreements with Nucky Thompson, a local politician and crime boss who runs the town on both fronts, Chalky is fiercely loyal to Nucky.

Actor Michael K. Williams said that playing Chalky was an honor. "[He]came from seeing his father be lynched and [only having] a limited education, but still had the finer things in life and gave his kids the best life he could. That’s the American dream right there. As a Black man, being able to play a role like that, especially in that time and era, it made me very proud and was a very humbling experience."

23. Winston Wolfe

Movie: Pulp Fiction

Year they first appeared: 1994

Actor: Harvey Keitel

Bottom line: If you’re in trouble, Winston Wolf is the man to call to clean up the mess. There’s no problem he can’t handle.

When hitmen Vincent Vega and Jules Winnfield end up with a dead body in their car, the Wolf comes over to cover the evidence in mere minutes.

The Wolf is a consummate pro, who has no time for small talk. He comes in, does the job, and leaves. And, of course, he’s wearing a tux the entire time.

22. Paulie 'Walnuts' Gualtieri

TV series: The Sopranos

Year they first appeared: 1999

Actor: Tony Sirico

Bottom line: Tony Soprano’s wise-cracking loyal foot soldier, Paulie Walnuts offers levity in moments that are dead serious, even when he’s the one doing the killing.

The standalone "Pine Barrens" episode, featuring only him and Christopher Moltisanti (Michael Imperioli) chasing a Russian mobster through the woods and getting hopelessly lost, remains a fan and critical favorite.

If you think Tony Sirico’s portrayal of Paulie Walnuts is a little too spot on, it’s alleged he was in the mob in the late 1960s, and he has admitted to spending several years in prison.

21. Sonny Corleone

Movie: The Godfather

Year they first appeared: 1982

Actor: James Caan

Bottom line: The eldest son in the Corleone crime family, Sonny was also its most impulsive and violent member. As the oldest, he was slated to inherit his father’s role in running the family, but he acted out of turn on too many occasions, which resulted in a hit taken out on his father (Vito, who survived) and led to Sonny's eventual demise.

While a hothead, Sonny showed empathy in a number of situations. When he was a child, he convinced his family to take in a homeless boy, Tom Hagen, who later became the family’s consigliere.

Sonny also was highly protective of his siblings and couldn’t bring himself to harm a person who was weaker than he was.

20. Keyser Söze

Movie: The Usual Suspects

Year they first appeared: 1995

Actor: Kevin Spacey

Bottom line: Roger "Verbal" Kint is a disabled, sad-sack con man being questioned by the cops for his role in a heist gone wrong.

He weaves the tale of the mysterious Keyser Söze, whose ruthlessness was said to be so great that he killed his own family after they were taken hostage by a rival gang, which he later massacres before going underground.

Söze's techniques in artful evasion are as legendary as his mercilessness. We don't find out until the end of the movie who he really is and when we do, we are gobsmacked.

19. Johnny Sacrimoni

TV series: The Sopranos

Year they first appeared: 1999

Actor: Vincent Curatola

Bottom line: Johnny Sack worked his way up the ranks in the Lupertazzi crime family until he eventually took it over. Despite his self-proclaimed desire to stay out of New Jersey’s business, he easily infiltrates the Soprano family in a number of ways using psychological tricks, including flattery and gossip.

However, he has no tolerance for gossip when it comes to his wife Ginny, who is massively overweight. When he hears a member of the Soprano’s crew make a joke about her, he demands his death to defend her honor.

18. Bonnie Parker

Movie: Bonnie and Clyde

Year they first appeared: 1967

Actor: Faye Dunaway

Bottom line: Bonnie Parker is the heart of "Bonnie and Clyde," the film based on real-life criminals, Bonnie Parker and Clyde Barrow (played by Warren Beatty). Bonnie writes poems about their bank-robbing adventures and generally romanticizes their time on the road.

Desperate times call for desperate measures. It is the Depression, after all, but the film never quite lets the duo off the hook. They look good, but they live fast and die young in a hail of bullets.

In the film, Dunaway looked as if she was a product of both the 1930s and the 1960s all at once. In fact, her look, down to the character’s penchant for berets, was a major influence on fashion in the years following its release.

17. Al Swearengen

TV series: Deadwood

Year they first appeared: 2004

Actor: Ian McShane

Bottom line: Al Swearengen is the tough as nails owner of Deadwood's Gem Saloon, a pimp, and controls the town's gold claims (and Deadwood in general) with an iron fist.

He will kill or hurt anyone to maintain control of Deadwood, and seek opportunity wherever he can find it, no matter its legality or questionable morality.

Deadwood fans love the character's cynicism and his extremely vulgar, cynical way of speaking, but if you were to meet him, you'd likely want to keep your distance.

16. O-Ren Ishii

Movie: Kill Bill Vol. 1

Year they first appeared: 2003

Actor: Lucy Liu

Bottom line: Of all the members of the Deadly Viper Assassination Squad, O-Ren Ishii (aka Cottonmouth) is the deadliest member, with the exception of Beatrix Kiddo, who kills her and most of the Crazy-88 in a duel at the House of Blue Leaves.

A Chinese-Japanese American, she became powerful enough to become "Queen of Tokyo's underworld" and rule over all the Yakuza clan leaders. When one of them objects, she simply cuts his head off to ensure the others remain in support.

How’s that for getting the point across?

15. Vincenzo Coccotti

Movie: True Romance

Year they first appeared: 1993

Actor: Christopher Walken

Bottom line: Vincenzo "Vincent" Coccotti's time in "True Romance" is short (at about 10 minutes) but certainly memorable. As the main antagonist, he sends a stream of hitmen to find Clarence and Alabama as they make their way out west.

Vincent makes only one appearance — to shake down Clarence’s dad, Cliff, who knows his minutes are numbered and decides to go out in a blaze of glory by telling the most offensive joke about Vincent’s heritage he can muster.

An angry Vincent admires the man’s bravery before pumping him full of lead.

14. Paulie Cicero

Movie: Goodfellas

Year they first appeared: 1990

Actor: Paul Sorvino

Bottom line: Paulie Cicero is the quiet, larger-than-life boss of the Brooklyn neighborhood where the "Goodfellas" main character, Henry Hill, grew up. Paulie takes Henry under his wing, shows him the ways of the wiseguy, and treats him like a son.

But every relationship has its breaking point. Henry's drug issues and bad decisions (including his role in the murder of Billy Batts) force Paulie to cut ties with Henry, which is something he clearly doesn't want to do.

13. Wilson

Movie: The Limey

Year they first appeared: 1999

Actor: Terrance Stamp

Bottom line: After decades in an English prison, Wilson flies to Los Angeles to avenge his daughter’s mysterious death. She was killed by her boyfriend when she threatens to tell police about a drug deal he’s involved in.

We learn through flashbacks that this was something she used to do with Wilson when she was a little girl because she was afraid of what would happen to him.

Wilson’s revenge drives the film forward, but at its core, the movie is about the consequences of following a life of crime and the regret and loss that accompany it.

12. Enoch Malachi 'Nucky' Thompson

Movie: Boardwalk Empire

Year they first appeared: 2010

Actor: Steve Buscemi

Bottom line: Nucky is both a politician and criminal in Prohibition-era Atlantic City. While he can be charming, kind, and generous to his friends and family, he also won't hesitate to kill anyone who threatens his power.

He makes more money from his criminal associations and running booze through the city than he does as a politician, but he stays partially on the up and up because his political connections greatly support his dealings in the underworld.

As he says: "If you wanna be a gangster in my town, then you'll pay me for the privilege."

11. 'Fat Tony' D'Amico

TV series: The Simpsons

Year they first appeared: 1991

Actor: Joe Mantegna

Bottom line: Even the town of Springfield has its own mafia and leading the local crew is Fat Tony, who, despite being a cartoon mobster, is not a one-dimensional character.

Sure, he has a predilection for violence, but he is sensitive, emotional, and a huge fan of "The Divine Secrets of the Ya-Ya Sisterhood."

When Fat Tony dies ("whacked by natural causes") his cousin, Fit Tony, takes his place and became Fit-Fat Tony before gaining enough weight to be a carbon copy of the original.

10. Sonny LoSpecchio

Movie: A Bronx Tale

Year they first appeared: 1993

Actor: Chazz Palminteri

Bottom line: Based on a real person of the same name, Sonny is a mob boss who takes a liking to an Italian-American teen named Calogero, much to his hardworking father’s dismay. While torn between the "life," and his father’s working-class values, it is Sonny who eventually steers Calogero away from becoming a criminal.

This film is semi-autobiographical for Palminteri (whose real name is also Calogero) and knew men like Sonny as a boy. "They’re not black-and-white. … Sonny is telling me the exact same things as my father! Sonny’s not telling me to be a wiseguy. He’s telling me the opposite. ‘Stay away from these guys and these bad influences ... Make something out of yourself ... Go to college.' That’s what makes these guys such a paradox and makes the story unique."

9. Jimmy Conway

Movie: Goodfellas

Year they first appeared: 1990

Actor: Robert De Niro

Bottom line: Because he’s half Irish, Jimmy will never become a "made" man in the mob, but his ruthlessness is equal to those of any true mob boss.

While he’s generally more cool and calculated than close cohort Tommy DeVito, Jimmy is equally violent and dangerous, and when his neck is on the line, he won’t hesitate to kill anyone who he deems a threat to his livelihood, including people he once considered friends.

Jimmy Conway is based on a real-life mobster, Jimmy Burke, who was said to be far less sophisticated and far more violent than his onscreen counterpart. De Niro makes him seem likable and he offers levity to a dark story with memorable lines, including "Never rat on your friends and always keep your mouth shut."

8. Bill 'The Butcher' Cutting

Movie: Gangs of New York

Year they first appeared: 2002

Actor: Daniel Day-Lewis

Bottom line: William "Bill the Butcher" Cutting is a Nativist who runs New York’s Five Points and leads his men to fight and defeat Irish immigrant gangs. He’s smart, sophisticated, and as an actual butcher, knows how to use a knife. (He refuses to use guns, stating they are dishonorable.)

Like many mob bosses, he also has a softer side. He provides neighborhood widowers and orphans with free meat, and his obsession with honor is equal to his ruthlessness. He hates corrupt politicians more than he hates the Irish.

7. Tommy DeVito

Movie: Goodfellas

Year they first appeared: 1990

Actor: Joe Pesci

Bottom line: Tommy is both hilarious and terrifying, and once he appears onscreen you know right away which side of his you'll want to be on. His hair-trigger temper causes him to make the fatal mistake of whacking a "made" man in a rival crew named Billy Batts.

Tommy leaves an impressive body count and some of the best scenes and quotes in the movie are his. Also, look for his homage to the "Great Train Robbery" at the end of the film.

6. Richard Harrow

Movie: Boardwalk Empire

Year they first appeared: 2010

Actor: Jack Huston

Bottom line: Richard excelled as a sniper in World War I and continued using those skills in Atlantic City working as a hitman for Nucky Thompson. Harrow has suffered disfiguring injuries to his face and longs for a normal family life, but is sure it is no longer available to him.

He doesn’t take pride in being a gangster, but he knows he's good at it (he admits to killing 63 people in Season 3), and it’s something he does to make a living. But he’s always haunted by what his life could have been.

5. Vincent Vega

Movie: Pulp Fiction

Year they first appeared: 1994

Actor: John Travolta

Bottom line: Vincent is a gun for hire for Marsellus Wallace and is a partner to hitman Jules Winnfield. Vincent does whatever Marsellus asks of him, whether it be executing a group of guys who stole his briefcase or taking the boss' wife out for a friendly dinner date.

The character of Vincent Vega is fun, curious, and lackadaisical and won Travolta an Oscar in 1995. The role single-handedly revitalized Travola’s career and placed Vega firmly in the pop culture lexicon.

4. Jules Winnfield

Movie: Pulp Fiction

Year they first appeared: 1994

Actor: Samuel L. Jackson

Bottom line: You know when Jules quotes Ezekiel 25:17 (or Tarantino’s version of it), you’re in for trouble. This was something he would say to his victim just before a hit, until he was nearly killed himself and believed he was saved due to a "miracle."

Jules is as philosophical as he is deadly. After this incident, he decides to the give up the life and "walk the earth." Some fans have theorized he got his wish.

3. Michael Corleone

Movies: The Godfather I, II, III

Year they first appeared: 1972

Actor: Al Pacino

Bottom line: Michael, who never intended to go into the family business, ended up being more ruthless than his father. Vito was a man of reason who would implore his enemies to consider other options. His son, however, just had them killed. Family members weren't off-limits either.

He eventually gives up all criminal operations by the late 1970s but doesn't get away so clean. Mary, his beloved daughter, dies as a result of his criminal lifestyle.

2. Vito Corleone

Movies: The Godfather I

Year they first appeared: 1972

Actor: Marlon Brando

Bottom line: Vito led a powerful criminal enterprise, but didn't take the role lightly. He was fair when the situation called for it and ruthless when he needed to be. He also had a conscience. Violence was a last resort and only occurred when all reason was exhausted.

Brando's portrayal of the don to end all dons is the gold standard by which all other gangsters are measured. His voice, lines, and his gestures are deciphered, parodied and mimicked to this day.

1. Tony Soprano

TV series: The Sopranos

Year they first appeared: 1999

Actor: James Gandolfini

Bottom line: Although he was a ruthless mob boss, Tony Soprano was also deeply conflicted. He suffered frequently from panic attacks, doubt, and emotional upheaval while dealing with familial and work issues.

"Tony Soprano was the first lead character to be a bad guy who did bad things, yet the audience chose to root for him. He’s a murderer, he’s a drug dealer, he’s a thief, he cheats on his wife, he hits all the sins," said Steve Schirripa, who played Bobby Baccalieri on the series. "Yet, for whatever reason, the audience likes him."