More from EW
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Most Method Mafioso: Don Vito Corleone, 'The Godfather'
The gold standard of made men. Years of training led to Marlon Brando's ''brilliant submersion in character,'' which decades later remains the definitive image of the mafia in pop culture.
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Biggest Emotional Roller Coaster: Christopher Moltisanti, The Sopranos
Thanks to a nuanced performance by Michael Imperioli, Tony Soprano's nephew was believable from the most hilarious high (an attempt to talk Sir Ben Kingsley into signing on for his hack job of a movie, Cleaver) to the most devastating lows (a battle with heroin addiction, the character-defining decision to bless his fiancée's murder). Christopher was unforgettable from the moment we met him to his last, gurgling breath.
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Most Casually Homicidal: Frank Lucas, American Gangster
Pro tip: Do not challenge this Harlem heroin overlord (Denzel Washington). Tango learned the hard way.
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Mustache-Twirliest: Stefano DiMera, Days of Our Lives
The bane of Salem is basically the Allen wrench of villainy. The only thing more fascinating than the nebulously nefarious Stefano's actual plotlines (especially ones where he dispatched comically evil genius henchman Rolf) was the behind-the-scenes battle between star Joseph Mascolo and Days' producers. Let's just say any actor who uses the phrase ''double crossing'' in a Soap Opera Digest interview was born to play bad.
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Gangster With a Heart of Gold: Roy Earle, High Sierra
He may have earned the nickname ''Mad Dog'' with his violent ways, but the gangster showed his true colors while caring for a mutt named Pard (played by star Humphrey Bogart's real-life dog Zero). Bogart broke out with the complex performance, which also showed Earle paying for corrective surgery for a disabled young woman (for whom he developed unrequited feelings), turning desperately to a taxi dancer for love, and meeting a heartbreaking end.
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Most Unlikely Mob Man: Nelson Van Alden, Boardwalk Empire
The former Prohibition agent (Michael Shannon) stumbled into organized crime when he murdered his partner and had to flee Atlantic City. He may be a newb, but he's taken to his new calling with eerie ease.
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Loosest Cannon: Tommy DeVito, Goodfellas
You think he's funny? ''I'm funny how? I mean funny like I'm a clown? I amuse you?'' In a scene that single-handedly won Joe Pesci his Best Supporting Actor Oscar, the rough-around-the-edges raconteur turned on a dime to wonderfully terrifying effect.
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Best Long Game: Don Domenico Clericuzio, The Last Don
The smartest thing any power player can do is quit when he's ahead. Though the octogenarian mafia head was apparently powerless to stop his empire from crumbling beneath his feet, the 1997 miniseries concluded with the ultimate twist: Don Domenico (Danny Aiello) had it in the bag all along.
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Most Musical Mobster: Fat Sam Staccetto, Bugsy Malone
The pint-sized club owner (John Cassisi) may have been plagued with fears that his rival would take over his business...but he was also locked and loaded with a gun full of custard and an Oscar-nominated Paul Williams track list. Win some, lose some.
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Most Skin-Crawling: Ben Diamond, Magic City
Despite his perfect tan, the Miami mobster (Danny Huston) had a dark, dark soul. You don't get the nickname ''The Butcher'' for nothing, and two dead wives (who died on operating tables while Ben watched) were just a few bodies on Ben's ever-growing pile. Most icky of all, when Ben discovered wife no. 3 was carrying on with his business partner's son, Ben was once again watching — as the paramours did the deed.
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Most Informed (and Informative): Frank Costello, The Departed
Thanks to Frank's elaborate tapestry of moles and doubled-down lies, the Southie mob boss gave us all whiplash during The Departed's kinetic, complex finale. It was a role so gaga, only an actor with the crazy-like-a-fox chutzpah of Jack Nicholson could pull it all together.
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Most Heartless: The Donbot, Futurama
We mean that in a literal sense. Anyone who crosses the Donbot will face the pain of his goons Joey Mousepad and Clamps. Word to the wise: Don't ever (ever) attempt to duplicate his meatball recipe.
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Certified Whack Job: Paul Vitti, Analyze This
After years of playing to type, Robert De Niro poked a little fun at his tough-guy reputation by playing a character as dangerous as he was neurotic in Harold Ramis's 1999 comedy, which snagged a 2002 sequel, Analyze That.
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Oscar-Bound Baddie: Mel Profitt, Wiseguy
Before he went on to score Academy Award gold portraying another untrustworthy character, Kevin Spacey played the pill-popping, turtleneck-rocking international evildoer for seven episodes in 1988. Fun fact: Despite his short stint on Wiseguy, Spacey's character was influential — he partially inspired a later cult-favorite series Profit.
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Most Vicious Mama's Boy: Cody Jarrett, White Heat
Perhaps it's his crippling headaches, perhaps it's the family history of mental illness (his father died in the loony bin), or maybe there's something to be said for the fact that Cody (James Cagney) is a grown man who sees nothing wrong with sitting on his mother's lap. Whatever is at the root of the killer's mania, it all added up to a character permanently etched into moviegoers' brains.
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Most Honorable Intentions: Frank White, King of New York
Sure, his moral compass goes in and out — Frank (Christopher Walken) presides over an ascendant drug ring and kills some associates because he disapproves of their participation in child prostitution and human trafficking, but it's all for a good cause! The underworld's answer to Robin Hood hopes to save a hospital in the South Bronx.
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WTF-iest Mafiosa: Jennifer Smith, General Hospital
No, your eyes aren't deceiving you. Yes, that is Roseanne. For three episodes in 1994, at the height of her eponymous sitcom's fame, the soap opera superfan (along with then-husband Tom Arnold) stepped in to play the heiress to Port Charles's organized crime syndicate.
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Style That Jumped the Shark(suit): Vinnie Antonelli, My Blue Heaven
Penned by Nora Ephron, the fish-out-of-water comedy starred Steve Martin as a rat relocated to suburbia who just couldn't let go of his big-city finery. If you think that concept isn't wacky enough, ponder this: Arnold Schwarzenegger was originally hired to play Vinnie.
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Best With a Catchphrase: Tony Montana, Scarface
''Say hello to my little friend!'' Find me a single person who hasn't, at some point, uttered those six words Al Pacino made iconic in 1983. It's okay...take your time....