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Films have produced countless iconic gangsters, but when it comes to fleshing out their lives, the small-screen has fitted the big-screen for concrete shoes. In the last decade and a half, series like Boardwalk Empire, The Sopranos, The Wire, Sons of Anarchy, and Justified have given viewers a new, more complete look at organized crime than short-running flicks ever could.
The rogues gallery of great television gangsters is growing every week. Bobby Cannavale's hot-headed, grudge-holding Gyp Rosetti on Boardwalk Empire, Harold Perrineau's vengeful grieving father Damon Pope on Sons of Anarchy, and William Forsythe's debt-wielding Constantine Alexander on The Mob Doctor are muscling out other characters and absolutely stealing their shows. Only time will tell where they rank amongst the best of all time, but our bet is that, in coming years, some of the G's featured in our countdown of The 25 Most Badass Gangsters in TV History will have to take it to the mattresses to fight them off.
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Written by Jason Serafino (@serafinoj1)
25. Al Capone from The Untouchables (1993-1994, CBS)
Played by: William Forsythe
This particular interpretation of The Untouchables wasn’t as great as the earlier ‘50s version, nor did it live up to the 1987 movie. Yet William Forsythe’s turn as the legendary Al Capone stood out amongst a sea of mediocrity. Forsythe’s performance was quiet, yet intense. At any moment you knew he could completely boil over, and just by looking at the burly shoulders of Capone, you knew he meant business.
It’s always tricky to bring such a well-known historical figure to the small screen, but Forsythe pulled this role off brilliantly. He’s the type of imposing presence that Capone must have been back in his prime. The simmering anger he put into his performance jumped right off the screen and made every episode completely unpredictable.
24. The Donbot from Futurama (1999-2003, FOX; 2008-present, Comedy Central)
Played by: Maurice LaMarche
As the bloated mechanical head of the Robot Mafia, the Donbot is the most feared crime boss in all of New New York and creates chaos across the galaxy.
Take the way he handles Bender, who has robot sex with Donbot's wife: After catching the two bots in the act, Mr. Don shot both of the cheaters and buried their metallic bodies. Screw marriage counseling.
When he's not righting domesting wrongs, so to speak, Donbot stacks paper through cigar smuggling and lottery swindling, proving that the world of Futurama really isn't that different from The Sopranos. Along with the help of his two associates, Joey Mousepad and Clamps, Donbot is the most intimidating stereotypical Italian robot on TV.
23. Jackie "John" Rhoades from "Nervous Man in a Four Dollar Room" (The Twilight Zone, October 14, 1960, CBS)
Played by: Joe Mantell
Appearing in the episode “Nervous Man in a Four Dollar Room,” Jackie Rhoades is an unsuccessful gangster with a spine made of jelly. In a seedy motel room, Jackie’s boss, George, orders him to kill a barkeeper or else he’ll kill Jackie in return. Consumed by guilt and fear, Jackie stews in his room, afraid to do anything. Then a voice calls to him: It’s his own reflection speaking to him from the mirror, but it turns out to be a much more violent, cutthroat, and proactive version of himself.
In typical Twilight Zone fashion, the two swap places, and this new Jackie Rhoades—now going by the name John—assaults his overbearing boss and promises his now meek reflection that he’s going to make something of himself. Rhoades goes from spineless underling to certifiable gangster in the blink of an eye.
22. Fat Tony from The Simpsons (1989-Presnt, FOX)
Played by: Joe Mantegna
Even in the small town of Springfield, organized crime is still seemingly everywhere, and one of the most prominent members of the only mafia family in town is Anthony “Fat Tony” D’Amico. Serving under Don Vittorio DiMaggio, Fat Tony usually leads a small group of soldiers in his never-ending quest to run his rat milk factory and his illegal gambling ring out of his “Legitimate Businessman’s Social Club.”
Always an ominous presence, Fat Tony has nearly killed every major character on the show, including Homer, Bart, Ned Flanders, Police Chief Wigum, and Mayor Quimby. Thanks to the on-point voice acting by Joe Mantegna, nearly every word out of Tony’s mouth is an absolute gem.
21. Gemma Teller Morrow from Sons of Anarchy (2008-present, FX)
Played by: Katey Sagal
Always guided by the need to protect her family, but Gemma Teller Morrow’s actions are incredibly malicious. She’s a master manipulator and does everything in her power to get to the top. Nothing exhibits this mindset more than when she, along with Clay Morrow (Ron Perlman), murdered her first husband and covered it up. This allowed the two to marry and run the Sons of Anarchy however they wanted.
These are the types of actions that land her on this list, and the character succeeds due to the fierce performance by Katey Sagal. She can flip the switch from affable to psychotic so quickly that it makes everything about Gemma that much more dangerous.
20. Vic Mackey from The Shield (2002-2008, FX)
Played by: Michael Chiklis
It might seem strange to have a cop on this list, but if you’ve ever seen The Shield you’ll know exactly why Vic Mackey here. He's not a by-the-books cop, and Mackey and his men would often work outside of the law in order to enforce it. Which included beating criminals, planting evidence, and even murder. There's little doubt that Mackey and his crew were a gang; the only difference here is that they wore badges.
This is all a means to an end for Mackey as he truly believes that his actions are completely justified as long as they produce the proper results. In addition to putting some criminals behind bars, Mackey also left a trail of bodies and crime behind him.
The sight of that bald head walking towards you in a dark alley is enough to make you think twice about committing a crime.
19. The Kingpin from Spider-Man: The Animated Series (1994-1998, FOX)
Played by: Roscoe Lee Brown
As one of Spider-Man’s most grounded villains, Wilson "Kingpin" Fisk pretty much runs all of the crime in New York City. Nearly every criminal, from the lowliest bank robber to the most sophisticated crook, works for Fisk in some capacity. He runs all of it from his impenetrable fortress, which is somehow located inside the hollowed-out Chrysler Building.
Even though Spider-Man: The Animated Series couldn’t show much in the way of violence and dangerous criminal activity, the Kingpin’s empire was still an overbearing force hanging over Spidey’s life. The best part about the Kingpin’s world is that while he is secretly running all of the city’s crime, he also moonlights as one of the most respected citizens of New York.
18. Louie the Lilac from Batman (1966-1968, ABC)
Played by: Milton Berle
Created specifically for the ‘60s Batman TV show, Louie the Lilac was a throwback to the classic gangsters from Hollywood’s golden age, with one exception: He was decked out from head to toe in purple.
Instead of trying to rule the drug or weapon trade like most gangs, Louie focused his efforts on the lucrative underground fragrance and flower market. He may wasn't a match physically for Batman, though we’re pretty sure the Caped Crusader had to spend weeks bleaching the hooker perfume smell out of his tights after tangling with Louie.
Louie the Lilac is the perfect example of not judging a book by its cover; his violet suits hid his malicious leanings. Plus, he was played by the legendary Milton Berle, who was packing more than his fair share of heat according to Hollywood lore.
17. Mags Bennett from Justified (2011, FX)
Played by: Margo Martindale
Think there's a bit too much testosterone on this list? Check out Mags Bennett, the matriarch of the Bennett family, whose hillbilly drug ring often went to lethal lengths to snuff out enemies. She monopolized the marijuana business on Black Mountain, not without the help of some poison-spiked "apple pie" moonshine. There's nothing sweet about that.
16. Margos Dezerian from The Shield (2002-2004, FX)
Played by: Kurt Sutter
Played to perfection by The Shield writer Kurt Sutter, who now runs Sons of Anarchy, Margos Dezerian was an ultra-violent hitman for the Armenian Mafia. On an already seedy show, he was one of the most ruthless characters, killing without thought and even cutting the feet off of his victims to keep as souvenirs that satisfied his foot fetish. Dezerian was about as deranged and despicable as they come.
15. Paul "Paulie Walnuts" Gualtieri from The Sopranos (1999-2007, HBO)
Played by: Tony Sirico
One of Tony Soprano’s closest associates, Paulie Walnuts is also the beloved HBO show’s most volatile mobster. With a quick temper and aversion to nearly everyone he has ever met, Paulie was an unpredictable member of the Soprano crime family. Regardless of his years of service, Paulie always felt like he was being looked over when it came to promotions within the family. He was hard-working and loyal, but he was always too hot-headed to really get the respect he deserved. Yet, even though that flaw was his Achilles heel, that's what made him so compelling.
14. Vinnie Terranova from Wiseguy (1987-1990, CBS)
Played by: Ken Wahl
Vinnie Terranova's backstory makes up for the fact that, technically, he wasn't a full-on gangster.
Terranova was tasked with infiltrating various mafia families in order to gather evidence and get the members of that crew sent to prison. To get his street cred for the job, Terranova was actually sent to prison for 18 months to gather intel on crime families and prove to them he wasn’t an undercover fuzz member.
That's one hell of a commitment, not to mention something you wouldn't do unless you’re ready to be whacked at any moment. At the same time, though, it caused a great amount of stress in Vinnie’s life. The constant pressures and lies were a running theme throughout Wiseguy, and the best part of the show was watching him twist like a hammock in the wind.
Even though he was just posing as a gangster most of the time, Vinnie Terranova was nothing less than a badass.
13. Ralph Cifaretto from The Sopranos (1999-2007, HBO)
Played by: Joe Pantoliano
During his brief time on The Sopranos, Ralph Cifaretto was one of the excellent drama's most interesting characters. Ralphie earned more than his fair share of money during his mob career, but he was also incredibly violent and untrustworthy. He took care of the business side of things without any trouble; when it came to his personal life, though, Cifaretto was a trainwreck.
Between killing strippers in public and setting fire to Tony’s beloved horse purely for the insurance money, Cifaretto could never stay in the good graces of his ill-tempered boss. It was only a matter of time before the two had it out in a brutal kitchen brawl that ranks amongst the series’ highlights.
Most of the praise for the character has to go to Joe Pantoliano's performance. The veteran actor brought an intimidating sleaziness to Cifaretto that cemented his status as one of the show’s more memorable troublemakers.
12. Clay Morrow from Sons of Anarchy (2008-2012, FX)
Played by: Ron Perlman
Clay Morrow is the former head of the SAMCRO biker gang. And it's "former" because, as the series has progressed, his greed and violence have eventually led to his dramatic downfall.
Before he turned into the shell of a gangster currently seen in season five, Morrow was the most powerful man in Charming, CA. He began the series as a guy who dispensed vigilante justice to keep his town safe (while moving guns for profit), but recently Sons of Anarchy fans have seen a much different Clay as he began to accept the drug trade into his community and plotted to have loved ones killed to cover up past sins (he and his wife Gemma killed John Teller, a club founder and her former husband, so they could run guns against his wishes).
Where he was once a badass you can root for, Clay quickly became a full-on villain, going as far as to murder one of his oldest, and totally innocent, club brothers, Piney, in order to save his own ass. The character comes to life through Ron Perlman's performance, in which the always on-point actor brings the right amount of pathos, ruthlessness, and vulnerability.
11. Avon Barksdale from The Wire (2002-2008, HBO)
Played by: Wood Harris
As the leader of a criminal drug empire in West Baltimore, Avon Barksdale was one of the single most powerful men in the state. At its best, his organization ran like a finely tuned machine, with Barksdale safely isolated from the drugs, virtually anonymous and like a ghostly street legend. Although he kept a low profile, he also made sure that no one ever tried to impede on his turf or power. He did this through violence and intimidation that knew no bounds or sense of morality. Simply put, Avon was a scary man with more power and backup than anyone should ever have.
His most memorable move was surrendering his second-in-command, Stringer Bell, to gunmen with a grudge after he discovered that his partner, who was attempting to go completely legit, had, without consultation or authorization, arranged the prison murder of Barksdale's nephew to ensure his silence and protect the organization.
10. Ellstin Limehouse from Justified (2012, FX)
Played by: Mykelti Williamson
The leader of the African-American enclave of Noble's Holler, butcher Ellstin Limehouse is a strict, no nonsense individual who acts as a sort of bank for other gangsters, including Mags Bennett, whose $3 million he hides inside an animal carcass. There is nothing that goes on that Limehouse does not know, and he doles this information out to criminals and lawmen alike whenever doing so benefits him personally.
A true-to-form, old school villain, Mykelti Williamson's performance elevates every sneakily charismatic monologue and disgusting tactic to another level. Limehouse is a man who's obsessed with keeping control of his backwoods underground community, and he does so by any means necessary, whether it means burning an employee with lye for failing him or hacking a rival gangster's arm off with a meat cleaver.
9. Chalky White from Boardwalk Empire (2010-Present, HBO)
Played by: Michael Kenneth Williams
Chalky White is the criminal head of the African-American community in Atlantic City, controlling liquor dispensation, the black vote, and the black work force. White men lynched his carpenter father when he was a boy but, thanks to the influence Chalky has gained despite his poor, uneducated upbringing, he is able to sit across from powerful white politician Nucky Thompson and dictate terms of agreements and even get away with killing KKK vigilantes.
Chalky’s character really comes together thanks to the acting by Michael Kenneth Williams, who brings an unpredictable intensity to the character that makes every scene he’s in one of the episode’s highlights.
8. Christopher Moltisanti from The Sopranos (1999-2007, HBO)
Played by: Michael Imperioli
As the young hot head in the Soprano family, Christopher Moltisanti’s tenure on the show was exceedingly unpredictable and violent (from shooting a baker for taking too long to serve him to pulling a gun on his boss and uncle in a jealous rage) but it was also some of the most compelling mob TV ever to hit the air. He was a man ruled by his personal demons, and because of that, he became a character of great sympathy and disgust. He could have risen through the ranks of the family if he had more patience and self-control, but he continuously got himself into bad relationships, drank too much, got hooked on drugs, and was a liability for the whole operation.
Moltisanti’s chaotic life was so engrossing because viewers could see themselves making similar mistakes if they were that young, rich, and powerful. He was incredibly flawed and human, but also incredibly fun to watch as you could never tell what he was going to do to piss Tony off next.
7. Stringer Bell from The Wire (2002-2008, HBO)
Played by: Idris Elba
Stringer Bell is one of the most complex characters on this list. The second in command in childhood friend Avon Barksdale's West Baltimore drug empire, he was more businessman than thug, but nonetheless capable of ruthlessness and violence whenever someone threatened their operation.
Bell took economics courses at community college, lived in a book-filled high rise apartment far removed from the streets, and attempted to shift the organization into legitimacy, but he was also the man who oversaw torture and interrogation and secretly ordered the murder of his partner's imprisoned nephew to prevent him from ratting. In the end, the incompatibility of his street reality and society leanings led to his bloody assassination. You truly cannot be half a gangster.
6. Al Capone from Boardwalk Empire (2010-Present, HBO)
Played by: Stephen Graham
No one in the history of American gangsters can touch Al Capone, so it shouldn’t come as a shock that the man makes it on this list for two separate portrayals. This one from Boardwalk Empire edges out the one from The Untouchables simply because this show airs on HBO where Capone is allowed to show off the brutal side we all know he had.
Boardwalk Empire shows young Capone making his way through the bootlegging world, while leaving piles of beaten, broken bodies in his wake. The man is a complete psychotic obsessed with power and money. There is an uncompromising rage that actor Stephen Graham captures perfectly as everyone needs to be on their guard at all times around Capone. His volatile unpredictability makes him the type of scary badass that we admire from afar, but wouldn’t want to go anywhere near.
5. Arnold Rothstein from Boardwalk Empire (2010-Present, HBO)
Played by: Michael Stuhlberg
By digging into actual mob history, Boardwalk Empire brought one of the most complex and powerful gangsters in U.S. history, Arnold Rothstein, to the small screen. Rothstein is perhaps best known as one of the men behind the 1919 Black Sox scandal, which left an indelible mark on sports in the real world. This show managed to give us a glimpse at the shady mind behind the event that still looms over baseball.
Played by Michael Stuhlberg, who hit the mainstream in A Serious Man, Rothstein is an incredibly sleazy, yet brilliant, mobster who harkens back to the classic Hollywood portrayals of organized crime. He’s classy, but conniving; he’s fairly meek, but utterly intimidating. Really, he’s the type of man you don’t want to mess with. It’s not that he’s physically imposing, but with a veritable army and unending supply of resources backing him up, you won’t come out of a confrontation with Rothstein alive.
4. The Greek from The Wire (2003-2008, HBO)
Played by: Bill Raymond
Much of The Greek’s life is a mystery. Hell, he’s not even really Greek apparently. But what we do know is that the man is the head of one of the most powerful international crime rings to ever hit television. Like most others, his army specializes in narcotics, but it’s also involved in other unsavory activity, such as human trafficking.
The Greek is a nasty old man who's willing to dispose of anyone or anything in his way of making money. Through-and-through, he is a ruthless capitalist, and there is no activity too illegal for him as long as it brings in cash. He’s also completely untouchable, thanks to his insulation from incrimination, Keyser Söze-like anonymity, and connections at the FBI that warn him when a criminal investigation is close. Despite his age, The Greek is virtually unbeatable.
3. Gustavo "Gus" Fring from Breaking Bad (2009-2011, AMC)
Played by: Giancarlo Esposito
He appeared friendly and harmless under the guise of a successful fast food franchise operator, but make no mistake about it: Gus Fring was a cold, despicable meth kingpin who used America's love of fried chicken to poison people and ruin communities for personal gain.
Fring was a savvy, organized businessman who compartmentalized his life extremely well, doing the devil's work while also playing the role of civic leader. He donated to the police force and shook hands with cops he tried to have killed; his laundromat housed a meth lab underneath; his fried chicken batter shipped with drugs concealed inside.
And to say that the two-faced menace was brutal and ruthless when it came to his empire is putting it mildly. In one of his most memorable displays of darkness, he personally slit the throat of a trusted underling like a chicken being sacrificed to a grill to keep other, more problematic employees in line. That he could do it all while looking like a mild-mannered, somewhat nerdy, businessman is enough to give anyone chills.
2. Enoch “Nucky” Thompson from Boardwalk Empire (2010-Present, HBO)
Played by: Steve Buscemi
If Boardwalk Empire has taught us anything, it’s that even if you’re involved in politics, you can still be a certified gangster. In the case of Enoch “Nucky” Thompson, the former sheriff and treasurer of Atlantic County, NJ, he made a fortune off of bootlegging with the other politicians from the area.
Thompson is one of the men that brought corruption to the Garden State, and thanks to the appropriately squirmy performance by Steve Buscemi, he’s one of the best characters on TV at the moment. Unlike most corrupt political figures with mob ties, Nucky isn’t afraid to get his hands dirty, as evidenced by the final episode of season two, when he murdered his own protege, a man he'd helped raise from boyhood, as a matter of business and payback for an assassination attempt on his own life.
1. Tony Soprano from The Sopranos (1999-2007, HBO)
Played by: James Gandolfini
Is there anyone else more worthy of this top spot than Tony Soprano? The broad-shouldered, overweight leader of the most prominent mob family in the Garden State brought movie gangster personality to the small screen, but with a far deeper examination of the psyche of a boss than the world had seen before (not even Michael Corleone sat for therapy sessions). During the course of the series, viewers saw Tony grow in stature as he rose through the ranks of the crime family thanks to his brutal style and street smarts.
But it's Tony’s family struggles and his personal foibles that make him feel like a true-to-life human, rather than a stereotype. This helped this otherwise despicable human being connect with audiences instead of repulsing them. Similar to Michael Corleone, Tony Soprano is the man you root for, and even when he’s busy killing foes in vicious mob style, he’s still a sympathetic figure.
Think about it: This is a man who rose to prominence and power off a business built on the blood of others, yet he still made viewers love him. Now that’s gangster.