One amazing thing about TV is that audiences can sympathize with anyone. Loki is a mass murdering war criminal; however, fans all over the world simp for him daily. Walter White is a power-hungry monster, yet his wife receives way more hate than Walter ever does. Like Loki and Walter White, viewers can also root for the ruthless mobsters at the center of David Chase’s gangster masterpiece, The Sopranos.
The Sopranos is a brilliant show about horrible people. No one is innocent. Almost every player is a killer who makes their living through the destruction of others. If we were to step back and ponder, with some degree of objectivity, which Sopranos’ personality comes out on top in terms of how bad they are?
10) Jackie Aprile Jr. (Jason Cerbone)
No other Sopranos character is more deserving of a firm slap to the face than Jackie Jr. The son of the deceased acting boss, Jackie Aprile, Jackie Jr. had everything handed to him. Instead of using his immense privilege to get an easy white-collar job, Jackie squanders everything. Even before he starts doing criminal acts, his demeanor, smirk, and body language is enough to make watchers loathe him.
Jackie is a lazy wannabe who flunks out of school to become a lackey to Ralph Cifaretto (Joe Pantoliano). What makes us genuinely despise Jackie is his treatment of Meadow Soprano (Jamie-Lynn Sigler). While dating her, he regularly cheats and lies to both her and Tony. His disrespect for Meadow awakens the parental instincts in viewers, who feel protective of one of the few genuinely nice characters in the show. After Meadow dumps him, Jackie’s recklessness peaks. He holds up a mob-run card game, bungles it miserably, carjacks a lady, then leaves his friend behind to be murdered by Christopher Moltisanti (Michael Imperioli). If Vito (Joseph R. Gannascoli) hadn’t taken Jackie Jr. out, who knows what kinds of wretched misdeeds he would have gotten into.
9) Phil Leotardo (Frank Vincent)
Phil Leotardo is an ambitious capo played by crime-movie legend Frank Vincent. Leotardo enters the fray when he’s released from prison as part of the “Class of ‘04”, along with mad-dog Feech La Manna (Robert Loggia) and Tony Blundetto (Steve Buscemi). Phil serves Johnny Sack (Vincent Curatola), patiently waits to strike, then orders hits on his colleagues to take the top spot in his crew, becoming the ultimate “Big Bad” of the final season.
Phil isn’t much worse than the average capo or boss in The Sopranos. He’s stubborn, misogynistic, violent, and arrogant, but that’s par for the course in the underworld. Yet, in a world where intolerance is a given, Phil’s bigotry shocks even his nastiest peers. His slaying of Vito is one of the ugliest in the series, a hate crime of such unspeakable cruelty that would make any crime-drama aficionado shudder. Even worse, Vito was married to Phil’s cousin, Marie, crushing her and mentally scarring her kids for life, to which Phil doesn’t even bat an eye.
8) Junior Soprano (Dominic Chianese)
From the inception of the series, Corrado Soprano Jr., aka “Uncle June” or simply “Junior” (Dominic Chianese), is framed as a pathetic, out-of-touch racketeer. The Fredo Corleone of the Sopranos family, Junior desperately wants to strike fear into the hearts of his underlings but lacks the ingenuity to do so. He has an insecure meltdown when his comare Bobbi Sanfillipo reveals that Junior performs a certain “generous” act in the bedroom, he tries to kill his nephew, and he orders the execution of the Soprano’s highest earner, Rusty Irish, on a whim.
Though he’s often shrugged off as a joke, the worst of his betrayals is unveiled in the prequel film, The Many Saints of Newark, where Junior secretly organizes the assassination of Dickie Moltisanti; all because Dickie laughed when Junior slipped and fell over. Like the death of Ned Stark, this one action has ripple effects throughout the entirety of the series.
7) Janice Soprano (Aida Turturro)
It’s a testament to the acting chops of Aida Turturro that Janice Soprano is one of the most hate-able characters in a show chock-full of unsympathetic, cold-blooded murderers. This unassuming, bratty sister of Tony’s is a mainstay of Season 2 and becomes increasingly shrewd throughout the show’s run. With Livia Soprano’s (Nancy Marchand) exit, the writers bulked up Janice’s role to serve as the avatar for Tony’s deep-seated childhood trauma. She is the successor to Livia’s particular brand of passive-aggressiveness.
Janice pretends to be open-minded, but she’s a wolf in sheep’s clothing. Despite her claims of liberalism, she blackmails a disabled worker, goes on racist tangents, and subtly suggests Richie Aprile should overthrow Tony. She has zero qualms about accepting her brother’s blood money and using it to maintain her layabout lifestyle. The many scenes of Janice upending Bobby’s life, shaming his children, and gaslighting him while he’s grieving the death of his wife, are beyond infuriating. Janice isn’t even a funny or interesting person; she has no purpose in life but to cause unnecessary drama. Janice doesn’t care about anyone or anything unless it directly benefits her. She is a true narcissist.
6) Livia Soprano (Nancy Marchand)
If it weren’t for Nancy Marchard’s passing, Livia Soprano would likely be higher on this list, as there was no floor as to how manipulative this matriarch could be. Livia steals every scene in the first two seasons: her constant complaining is always an excellent highlight. Livia is Uncle June’s puppeteer, whispering in his ear like a devil on his shoulder. Junior only has the nerve to order the hit on Tony because Livia gives the go-ahead. Don’t mistake her unending whinging for weakness; it’s merely a cloaking mechanism so that she can hide in plain sight. There are many moments, like in the hospital when she rats out Tony to Artie Bucco, where you question, “Wait. Is she senile or a Machiavellian genius?”.
An illuminating moment comes in the 7th episode, “Down Neck,” in a flashback, where Livia convinces her husband to stay in the mafia instead of moving the family to Reno. She does this by threatening to smother their kids. Livia is the brains in the Sopranos household; no one notices they’re dancing to her tune. Even four seasons after her death, Livia’s nihilistic attitude is still poisoning her family, weighing heavily on the soul of her depressed grandson, AJ (Robert Iler).
5) Tony Soprano (James Gandolfini)
Because he is our protagonist, played with powerful charisma by the late, great James Gandolfini, it’s sometimes easy to forget that Tony Soprano is a monstrous villain. Tony is abusive to almost everyone he comes across, exacerbated by his anger issues, gambling addiction, and unparalleled mommy issues. A glutton in every sense, he is a severely disturbed individual in total denial about how wicked he is, passing off his heinous actions as “the way things are.”
Despite his wife staying with Tony through his abuses and endless adulterous escapades, he consistently betrays her trust and screws over Carmella’s construction project, unable to reconcile her enterprising spirit with his male chauvinism. Tony can commit the worst crimes imaginable, then turn around and claim to be the real victim. What saves him from the #1 spot is his genuine love of animals, righteous anger at violence against women (sometimes), and occasionally progressive views relative to his cohorts (which isn’t saying much).
4) Paulie Gualtieri (Tony Sirico)
Paulie (Tony Sirico) is the funniest Sopranos character. He’s responsible for the most memorable malapropisms in the series. He’s also a petulant, violent manchild like Tony. Whereas similarly ranked members of the family like Silvio (Steven Van Zandt) or Big Pussy (Vincent Pastore) are slick enough to put on a gentler face when out in broader society, Paulie has no idea how to hide his brutality. Even under the pretense of committing acts of kindness, he makes everyone’s lives more miserable, such as his run-in with gardener Sal Vitro.
What makes Paulie so scary is that he lacks any self-awareness. When he is confused or feels slighted in any way, he lashes out in fits of ultra-violence. In many ways, he is the American equivalent to Begbie from Trainspotting, unstable, petty, and impossible to reason with. The only thing preventing Paulie from being the most unhinged cast member is his undying loyalty to Tony, who keeps Paulie on a tight leash.
3) Richie Aprile (David Proval)
Richie (David Proval) is the villain we all love to hate. A vicious, uncaring ghoul, he’s not the most complex character, though his engagement to Janice is inexplicable and suggests a hidden depth beneath his moody exterior. Richie barges into season 2 and throws everything into a tailspin, especially after slamming his car into Beansie Gaeta, disabling him for life, much to the chagrin of Tony. His calm, monotone threats are enough to send a shiver down even the toughest criminals’ spine. Richie can’t be bargained or reasoned with, like an old, leathery Terminator.
According to Silvio and Janice, when Richie suspected his son was gay, he immediately disowned him. The key conflict of Season 2 revolves around Richie plotting to overthrow Tony to become boss of the family, but luckily his plans never come to fruition, as his physical abuse of Janice was one step too far for her. Richie’s death at the hands of Janice is probably the most satisfying in the entire series.
2) Ralph Cifaretto (Joe Pantoliano)
Joseph Pantoliano is a national treasure. No one plays an insidious creep quite like him. His portrayal of Ralph Cifaretto is his best role, even better than his portrayal of a cowardly husband in Bound. Ralph is a microcosm of how the characters in The Sopranos are their own worst enemies. When he beats Tracee to death, angering Tony, all Ralph has to do to survive Tony’s rage was to let go of his ego a little, but remorse isn’t on the cards for him.
A sadomasochist who abuses women, Ralph is about as disgusting as a human being can be. You know you’re a real scumbag when Paulie, Tony, and Johnny Sack think you’re too unpleasant to be around. Out of all the despicable crimes Ralph is responsible for, it’s delightful that Tony kills him over a horse. Ralph was so despised that his death was barely investigated, as seemingly everyone had the motivation to kill him.
1) Christopher Moltisanti (Michael Imperioli)
Christopher Moltisanti may be the most loathsome lead character in TV history. Unlike Tony’s love of animals or Paulie’s humanizing foolishness, Cristopher has zero redeemable features. He is humorless and miserable. Even when he’s at his most vulnerable, it’s apparent that there’s no decency inside. His relationships are all self-serving; he’s ungrateful, narrow-minded, and a brilliant example of the Dunning-Krueger effect in action. It’s bad enough that he makes everyone call him “Christopher” instead of “Chris,” but his crimes are even worse. Christopher has all of Tony’s flaws, but he lacks the likeability Tony exudes, resulting in severe jealousy on Christopher’s part.Christopher Moltisanti may be the most loathsome lead character in TV history. Unlike Tony’s love of animals or Paulie’s humanizing foolishness, Cristopher has zero redeemable features. He is humorless and miserable. Even when he’s at his most vulnerable, it’s apparent that there’s no decency inside. His relationships are all self-serving; he’s ungrateful, narrow-minded, and a brilliant example of the Dunning-Krueger effect in action. It’s bad enough that he makes everyone call him “Christopher” instead of “Chris,” but his crimes are even worse. Christopher has all of Tony’s flaws, but he lacks the likeability Tony exudes, resulting in severe jealousy on Christopher’s part.
Christopher is the ultimate cry bully, a guy who can assault others without hesitation but throws a hissy fit if someone even looks at him funny. Probably the most shocking episode, “Long Term Parking,” involves a cowardly Christopher ratting on his fiancé Adriana (Drea de Matteo) for being an informant, leaving Silvio to execute her. The way he treats Adriana, especially when he finds out she may not be able to have kids, is among the most distressing behavior exhibited on television. His wife and daughter are fortunate Tony murders Christopher before he can ruin their lives.