In the world of Boardwalk Empire, there's no such thing as clear-cut "good guys" and "bad guys." One of the most sympathetic characters to date, Richard Harrow, is a skilled marksman who has lost count of the number of people he's killed. Married Northside leader Chalky White has sullied his reputation and that of his family by running around with jazz singer Daughter Maitland, his true love. And we'd need a separate article to name every time series protagonist Nucky Thompson has lied, cheated and killed in the space of four seasons. But like Don Draper, Walter White and Tony Soprano before him, we're rooting for Nucky to come out on top, which is why, regardless of his murderous tendencies (at times), he can't necessarily be considered "evil." Still, Atlantic City has been graced with a substantial number of contemptible, charismatic and utterly incendiary gangsters that embody the very definition of the word "villain." As the fourth season wraps up this Sunday, check out our list of Boardwalk Empire's most vile residents, past and present. —Sarene Leeds
He didn't survive past the pilot, but Margaret's boorish, abusive husband led her directly into the cyclone that is life with Nucky Thompson. The black eye on a heavily pregnant Margaret's face doesn't go unnoticed by Nucky when she first beseeches him for financial assistance. The big wad of cash she comes home with that day doesn't go unnoticed by Hans, either. After Hans' latest beating causes Margaret to miscarry and puts her in the hospital, Nucky, unable to ignore his fascination with this sad-eyed Irish woman, flexes his gangster muscles for the first time in the series by making Hans sleep with the fishes (he's discovered in a fishing net along with the catch of the day). Her dangerous husband eliminated, Margaret embarks on a far more dangerous relationship in the coming episodes and seasons – with Nucky Thompson himself.
Never get into business with a butcher, especially one adept with a knife. Philadelphia gangster Manny Horvitz was regularly seen wearing a bloodied apron and fondling his meat blades, which only added to his menacing cadence. But even when his weapon of choice was a gun, the outcome was no less horrifying. At the end of Season Two, Manny ruthlessly shot and killed Jimmy's wife, Angela Darmody, and her lover Louise in cold blood merely because they were in the wrong place at the wrong time. "Your husband did this to you," Manny sneers at a helpless Angela before taking her life. Early in Season Three, however, Angela's death was avenged by her friend Richard Harrow, who shot Manny squarely in the eye on New Year's Day, 1923.
Behind Charlie "Lucky" Luciano, Gyp Rosetti and now Dr. Valentin Narcisse, there was New York mob king Joe Masseria, standing in the shadows and working the puppet strings of all the city's lower-level gangsters. He epitomizes the old-world ways of conducting business (in his case, speaking primarily in Italian, and expressing doubt over Luciano's partnership with the Jewish Meyer Lansky), but it makes him no less powerful along the Eastern seaboard. He was the brains behind Owen Sleater's jaw-dropping Turkish-bath murder in Season Three, sending the Irishman back to Nucky (and his pregnant mistress, Margaret) stuffed in a wooden crate. By the end of Season Four, Masseria had joined forces with Narcisse to control the burgeoning heroin trade, making him all but untouchable.
Whenever I watch this scene, where a young Scarface sings "My Buddy" to his deaf son, I have to force myself to remember that the man strumming the ukulele is one of the most notorious criminals in history. And that's what makes Boardwalk's version of Al Capone such a fascinating character – his love for his family is just as strong as his disdain for his enemies. Al thinks nothing of shooting a random police officer minding his business, reading about the Leopold and Loeb case, merely because his brother, Frank Capone, died at the hands of the law. He can be a pragmatic gangster, however. When Al and his men arrived in Atlantic City to assist Nucky in the fight against Gyp Rosetti in Season Three, he announced: "We need a bath, some chow, then you and me sit down, and we talk about who dies."
He started out on the "right" side of the law, as a Prohibition agent, but even before Nelson Van Alden went on the lam for drowning his partner, Agent Sebso (for the crime of being Jewish), he was always one of the series' most despicable characters. Whether he was pocketing the cash from liquor raids or neglecting his whiny baby mama Lucy Danziger, the deeply religious, sexually repressed Van Alden was just asking for a punch in the face. Once settled in Cicero, Illinois, with his new Norwegian wife and their children in Season Three, Van Alden seemed to be loosening up. And by Season Four, Van Alden had transitioned from unwitting errand boy for the Capones into a Walter White-esque gangster with a hard-on for bloodshed, big bucks and boning (Sigrid).
It's next to impossible to find a more damaged soul on Boardwalk Empire than former Atlantic City showgirl Gillian – her deceased son, Jimmy, comes in at a close second. Raped and impregnated at 13, it's understandable that Gillian grew up with a warped sense of right and wrong, but her sins are far more heinous than those of most mobsters: She committed incest with Jimmy, drowned an innocent man for her own financial gain, tipped off Gyp Rosetti to Nucky's whereabouts one night – resulting in a bomb at Babette's Supper Club that killed starlet Billie Kent – and worst of all, tried to erase her grandson Tommy's memories of his parents. Her arrest last week by her lover, Roy Phillips (who turned out to be a Pinkerton detective), while tragic, is a well-deserved comeuppance for her nefarious deeds.
Warren Knox's "baby face" and his innocent, Midwestern charm belie his true nature – a vicious, unhinged member of the Bureau of Investigation with the myopic goal of taking down Nucky Thompson's operation. He solidified his role as one of Season Four's most diabolical villains in Episode Five, where he tortured Nucky's manservant, Eddie Kessler, to the point that the German native's only chance at peace was to commit suicide. Knox – real name Jim Tolliver – is also enmeshed in a game of one-upmanship with his law-school frenemy, the newly named director of the Bureau, J. Edgar Hoover. Unable to face Hoover empty-handed, Knox blackmails Nucky's brother, Eli, into turning informant – for the price of keeping his son, Willie, out of jail.
The primary antagonist of Seasons One and Two, the Commodore groomed Nucky Thompson to take over as Atlantic City boss. Trouble was, once that happened, the aging mobster didn't like the view from the cheap seats. By the end of the first season, the Commodore had enlisted both Eli and Jimmy to assist in his coup d'état, turning two of Nucky's closest confidants against him. Even a severe stroke the following season didn't incapacitate him for long – although it allowed Gillian to unleash her pent-up rage at him for raping her all those years ago (yep, the Commodore is Jimmy's dad – awkward!). In the penultimate episode of Season Two, Jimmy, in a drunken stupor, attempts to strangle Gillian, who made several callous remarks in the wake of his wife's death. The Commodore saves her by stabbing Jimmy in the shoulder with a spear, but his attempt to kill his own son is thwarted when the younger, stronger Jimmy finishes off his father instead.
When New York sociopath Gyp Rosetti's reign of terror was finally brought to a screeching halt in the Season Three finale, everyone – not just Nucky – breathed a huge sigh of relief. Just look at this guy the wrong way and you could find yourself drenched in gasoline and lit on fire, while Gyp numbly stares you down. A second-rate gangster consistently emasculated by his wife, daughters and Joe Masseria, Gyp's hotheaded behavior was understandable, although certainly not forgivable. His life on the Boardwalk didn't last more than 12 episodes, with him getting stabbed in the back – literally – by his right-hand man, Tonino Sandrelli. But Bobby Cannavale's stellar, frightening performance solidified Gyp's exalted place in the series' history as he picked up a Best Supporting Actor Emmy (the only acting award given for Boardwalk to date) earlier this fall.
The most dangerous villains are also the most charismatic, and newcomer Dr. Valentin Narcisse is no exception. The Trinidad native and Marcus Garvey supporter presents himself as an early proponent of African-American civil rights, but in reality, he's a merciless killer who deeply lacks any sort of empathy. He brutally lynched a bigoted white woman who displeased him, and in one of the season's biggest twists, it's revealed that Narcisse murdered Daughter Maitland's prostitute mother before taking the eventual blues singer under his wing. Narcisse's grasp of Atlantic City's Northside – and his subsequent war with Chalky White – has been one of the most riveting story lines of the season, and the Season Four finale is certain to be a real nail-biter as the two men prepare for a showdown.