This show, well-known for portraying The Mafia in a very unsympathetic light (no romanticism whatsoever), several viewers began to believe that this trope was the intention of the show. Given that, it's not hard to imagine that many of the characters were written to be unlikable.
- Livia Soprano, Tony's abusive mother. Livia derives little pleasure save from hurting others and making them miserable. She psychologically tortures Tony as much as she can and has a hit put out on him in revenge for trying to put her in a nursing home. Her abuse of Tony has been there for years.
- Janice Soprano. A toxic, annoying, manipulative, contemptible woman with a parasitic life that only generates problems for the actual money earners.
- From "Another Toothpick", Salvatore "Mustang Sally" Intile, as expected from a psychopathic Domestic Abuser. Ralph Cifaretto says (with disgust, to boot) that Salvatore threw a hot dog vendor off the second-floor mezzanine at Giants Stadium for serving too many onions on his hot dog. He is callous and has a morbid sense of humor, joking about the attack on Bryan Spatafore.
- Johnny Boy Soprano. Given that he was a psychopathic mobster who preyed on honest working people and made Tony what he is, it's not hard to imagine that Johnny Boy was written to be unlikable.
- Richie Aprile is one of the most despised characters on the show for his malicious personality and for having zero redeeming qualities. He's such a loose cannon that Tony has to stop him from killing gamblers. He also beats his fiancée for nothing more than saying she'd accept his son for being gay, which culminates in her snapping and murdering him herself. Besides that, he has numerous observations by other characters that he cares about no one but himself. Richie's worst act, however, was Beansie's brutal paralyzation, just for refusing to be shaken down, and continued to threaten him.
- Ralph Cifaretto. Given that he's a toxic, socially repugnant individual willing to kill his own pregnant girlfriend with his bare hands, it's easy to argue that his character was crafted to invoke this trope. Heck, even Tony and Paulie hate him. He tried to be better after his son's accident, but even that did not stop Tony's bubbly resentment, which culminates with him brutally murdering Ralph.
- Phil Leotardo is openly sadistic, volatile, brutal, and confrontational, utilizes bullying and fear against his victims, sets Vito up to be tortured and killed, orders his henchmen to kill Bobby and Silvio, and before that, he threatens to inflict the cruelest possible death upon Tony Blundetto. His brutality makes Tony Soprano himself look like a sane boss in comparison.
- Dominic "Fat Dom" Gamiello, Phil's dragon. He has no characterization outside of being a brutal mobster who takes rather obnoxious glee at gloating over Vito's death to Sil and Carlo.
- The two Jasons — Jason Gervasi and Jason Parisi. A duo of irresponsible, selfish, lazy, sadistic jerkasses. One of their cruelest acts was in "Walk Like a Man", where they used A.J.'s SUV to take a gambler into the woods and torture him by pouring sulfuric acid on his toes.
- Jesus Rossi, "The Employee of the Month", managed to become one of the most despised characters in the show in a matter of minutes after brutally raping Dr. Melfi in a parking garage. What makes this even worse is that he is eventually released after being arrested simply because there was not enough evidence. Melfi has a chance to hire Tony to assassinate him in revenge but she decides not to which makes Rossi one of the few characters in the show to be an outright Karma Houdini.
