HBO’s The Sopranos is a brilliant show about horrible people. No one is innocent. Almost every player is a killer or a master manipulator who makes a living through the destruction of others. If we were to take a moment to step back and ponder, with some degree of objectivity, which Sopranos’ personality comes out on top in terms of how bad they are?
Honestly, the choices are endless, but there are some players, like New York’s Phil Leotardo and Richie Aprile, who have little to no redeeming qualities and are just downright rotten to the core. From Tony’s oldest sister, Janice Soprano, to the sick and twisted Ralph Cifaretto, these are 10 of the worst characters from The Sopranos, ranked from bad to simply pure evil.
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10. Janice Soprano
Played by Aida Turturro
Janice Soprano is one of the most hated characters in a show chock-full of unsympathetic, cold-blooded murderers. This unassuming, bratty older sister of Tony’s is a mainstay of Season 2 and becomes increasingly shrewd throughout the series. 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 and the successor to Livia’s particular brand of torment.
Despite her claims of liberalism, she blackmails a worker with a disability, goes on racist tangents, and has zero qualms about accepting her brother’s blood money 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 beloved wife are beyond infuriating. Janice doesn’t care about anyone or anything unless it directly benefits her, making her one of the worst characters in the series.
9. Mikey Palmice
Played by Al Sapienza
Mikey Palmice is a loyal and sadistic old-school gangster who follows orders and does what he’s told, and even though he was killed off at the end of the show’s first season, he left a lasting (and sinister) impression that earns him a spot on this list. Mikey has been Junior Soprano’s (Dominic Chianese) right-hand man for many years and is responsible for every ordered hit.
Similar to other Mafiosos, Mikey adds a bit of showmanship to his work, such as delivering Brendan Filone (Anthony DeSando) with a Moe Green special in season 1, episode 4, “Meadowlands.” Mikey’s charismatic charm and sarcasm make him an unreadable character who will greet you with a welcoming smile one second and deliver a brutal beat down the next. While it’s expected for him to put on a tough and empathetic face, he doesn’t take it off when he gets home and berates and degrades his wife, Jojo (Michele Santopietro), out of pure amusement.
8. Corrado “Junior” Soprano
Played by Dominic Chianese
From the inception of the series, Corrado “Junior” Soprano is portrayed as an insecure, out-of-touch racketeer who has constantly lived in the shadow of others, specifically his younger brother and Tony’s father, Johnny Boy. He desperately wants to be respected and treated like a boss, but he lacks the ingenuity and confidence to be a leader and, instead, tries to earn it by trying to strike fear into others.
Even though he takes over as boss of the family, he’s so self-involved and enamored with the title that he fails to realize that Tony is still secretly running things behind his back. Despite Junior’s long list of qualms, he does have his moments of honorable intentions, mainly when he refuses to flip on Tony in one of The Sopranos‘ best episodes, “I Dream of Jeannie Cusamano,” in exchange for leniency, which is the only reason why he’s not ranked higher on this list.
7. Tony Soprano
Played by James Gandolfini
Played with powerful charisma by the late, great James Gandolfini, it’s sometimes easy to forget that Tony Soprano is a monstrous human being. Tony is horrible to almost everyone he comes across. Whether it’s a stranger or his wife, no one is spared from his rage and bullying tendencies. A glutton in every sense, Tony is a severely disturbed individual who is in total denial about how wicked he is, rationalizing heinous actions as “the way things are.”
He constantly uses his “lifestyle” as an excuse for verbally and mentally abusing his family and falls back on his panic attacks whenever someone confronts him about his behavior. Tony can commit the worst crimes imaginable, then turn around and claim to be the real victim, which is a classic ploy by every narcissist. 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).
6. Paulie Gualtieri
Played by Tony Sirico
Paulie Gualtieri (Tony Sirico) is one of the funniest Sopranos characters and is also responsible for some of the most memorable malapropisms in the series. Unlike similarly ranked members of the family like Silvio Dante (Steven Van Zandt) or Big Pussy (Vincent Pastore) who are smart 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 (Louis Mustillo). What makes Paulie so scary is that he lacks any self-awareness and impulsive control, which sometimes lands him in hot water with Tony, such as the incident with the Russian, Valery (Vitali Baganov) in season 3, episode 11, “Pine Barrens.” If it weren’t for his sense of humor and undying devotion to his mother, Paulie would easily rank higher on this list.
5. Phil Leotardo
Played by Frank Vincent
Phil Leotardo is an ambitious and entitled capo who enters the fray in season 5 of The Sopranos when he’s released from prison as part of the “Class of ‘04.” Phil isn’t much worse than the average capo or boss in The Sopranos. Phil is 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.
When he discovers that Jersey capo, Vito (Joseph R Gannascoli) has been unfaithful to his cousin, Marie (Elizabeth Bracco), with other men, he becomes bound and determined to whack him. Not only does he accomplish this in season 6, episode 11, “Cold Stones,” but it is one of the ugliest executions that would make any crime-drama, gangster-loving aficionado shudder. Even worse, Phil fails to think about Marie and the impact Vito’s death would have on her and their kids and, instead of trying to genuinely help out, he expects Tony to take care of the mess he created.
4. Livia Soprano
Played by Nancy Marchand
Tony’s mother, Livia Soprano, is a classic martyr who loves to play dumb to the fact that she’s the one who calls the shots in the powerful Soprano family. She plants seeds of deception and paranoia in Junior’s head by vaguely whispering in his ear like a devil on his shoulder. While Junior had a legitimate reason to whack Tony, Livia basically set the plan in motion simply out of spite and wanted her own son dead because he placed her in Green Grove, which she eventually started to enjoy!
An illuminating moment comes in season 1, episode 7, “Down Neck,” in a flashback, where Livia threatens to stab young Tony in the eye with a fork. With a mother like that, it’s no wonder why Tony has so many issues with women and expressing his emotions. Her constant negativity, back-handed compliments, and her desire to let her son be murdered because he was trying to take care of her makes her one of the absolute worst characters in the show.
3. Christopher Moltisanti
Played by Michael Imperioli
Unlike Tony’s love of animals or Paulie’s humanizing foolishness, Christopher Moltesanti has little to zero redeemable qualities and ranks as one of the coldest characters in the series. Christopher has always had a cinematic idea of what it’s like being in the mafia and his determination to earn his button and prove himself instead of working his way up the ranks speaks volumes about his over-inflated ego.
There are dozens of reasons why Christopher earns a spot on this list, like senselessly murdering a waiter who complained about his lack of a tip and smothering poor Cosette, but nothing compares to his mistreatment and shocking betrayal of his fiancé, Adriana (Drea de Matteo) in the sad Sopranos episode “Long Term Parking.” The way he treats her, especially when he finds out she may not be able to have kids, is among the most distressing behaviors exhibited on television, and how he allows Tony to lure Adriana out is just cruel.
2. Richie Aprile
Played by David Proval
Richie Aprile is Jackie Aprile’s (Michael Rispoli) older brother and a vicious sociopath who has a deadly stare that would rattle even the toughest criminal. Richie makes his entrance in a savage episode of The Sopranos, “Toodle-Fu*king-Oo,” where he pays a seemingly friendly visit to his former associate, Beansie Gaeta (Paul Herman). When Beansie refuses to kick up to him, Richie reveals his true, violent colors by smashing a pot of coffee across his face and eventually running him down with his car, paralyzing Beansie for life.
Richie reacts to a level 1 situation with a level 10 response, making him an unpredictable ticking time bomb who is only loyal to himself. Between plotting to take Tony out and disowning his son for being gay are just the tip of the iceberg of reasons why Richie is one of the most evil characters in The Sopranos. What solidifies Richie’s spot on this list is when he punches Janice in the face. Unfortunately for him, that was one step too far for Janice, who without hesitation pulls a gun and fires two satisfying shots into his chest.
1. Ralph Cifaretto
Played by Joe Pantoliano
A sadomasochist who abuses women, Ralph Cifaretto is about as disgusting as a human being can be and the most evil character in The Sopranos. The absolute worst quality about Ralphie is that he’s a wolf in sheep’s clothing and manages to fool others outside this thing that he’s just an everyday guy. Ralphie is a sick fu*k who has zero respect for human life and showcases this by beating a Bada Bing girl, Tracee (Ariel Kiley), to death in season 3, episode 6, ‘University,’ and intentionally setting Jackie Jr. (Jason Cerbone) up simply out of spite.
After the senseless murders of Tracee and Jackie Jr., tensions are high between him and Tony, but when Ralphie’s son almost dies in a bow and arrow accident, Tony thinks he might be turning over a new leaf. Sadly, that glimmer of hope is quickly dashed after Tony realizes that Ralphie killed Pie-O-My to collect on the insurance, which is essentially the final straw for Tony. Ralphie did bring a little comedic relief to the show, but no joke or good deed could ever redeemhis long list of evil and sin.