There are too many reasons whyThe Sopranosis an all-time great show to count, but an undeniably big one is its vast array of very flawed – and consistently interesting – characters. Plenty of them even show an inability to change in meaningful ways, like most TV characters might be expected to do, but they remain engaging either in spite of that, or simply because of that (and the quality of the writing and acting help ensure this becomes a feature, rather than a bug).
Everyone was flawed and capable of having moments that made them come across poorly, to say the least, but a few characters inThe Sopranoswent the extra mile on the irritation front. It’s pretty subjective, picking such characters, and most ofthese characters are still good, if not essential to the show, especially since some of the most irritating are the source of a great deal of compelling drama. Also, if a character is outright villainous or hateable, rather than annoying (or maybe unlikable and annoying), then they might not be featured here (so, no Jesus Rossi, from theinfamous season 3 episode “Employee of the Month”). And neither of Tony’s kids, either. A.J. is whiny and annoying, sure, but he’s also a kid for most of the show, and it doesn’t entirely feel like his fault that his teenage years were particularly bratty; he became a little more sympathetic – and even tragic – by the final season, in any event.
This article will contain some spoilers for all six seasons of The Sopranos.
The Sopranos
10Elliot Kupferberg
Appeared in 14 episodes
It’s funny picking on relatively minor characters and singling them out for things that are technically less serious than some of the acts many of the main characters do. If you don’t find it funny, too bad, because that’s why Elliot Kupferberg is here. Essentially, he’s the shrink of the show’s main shrink, Dr. Melfi, whose primary role in the show is being in charge of Tony’s therapy sessions.
Anyway,he seems either bad at his job or kind of shady and manipulative; maybe even a bit of both. He also has a stupidly oversized water bottle, and lets slip some stuff he shouldn’t have at a dinner party late in the show’s final season, breaching the doctor-patient confidentiality he had with Melfi. And he ends up inadvertently screwing Tony over, playing a role in convincing Melfi to drop her patient of almost a decade for goodin the penultimate episode of the series.
9Janice Soprano
Appeared in 49 episodes
It was tricky figuring out whether to put Janice here or not. She is pretty terrible at times, but so is just about everyone else in the Soprano family. She acts as a source of irritation for Tony, especially once his mother’s gone (more on her in a bit), but at the same time, he’s also not the greatest brother to her,being willing to act out in cruel waysfor petty reasons.
So, Janice is sometimes victimized by Tony, and she’s also incredibly mistreated by Richie Aprile (we’ll get to him later, too), to the point whereshe shoots him after he gets physical with her… and that is the key moment that makes Janice sort of awesome, at least for a while, and not entirely worthy of being mentioned here. Still, by and large, Janice is an intentionally grating premise most of the time, but she’s also a great character for similar reasons to her mother, Livia. You can get annoyed with her the way Tony often does, butThe Sopranoswould’ve been a technically lesser show, had she never appeared on the show.
8Brendan Filone
Appeared in 4 episodes
Like Janice, Christopher Moltisanti rides the line between annoying yet also great as a character. Maybe, like Paulie, he’s more irritating to characters in the show (like Tony) than he is annoying to those watching at home, with a screen separating viewer from moron(s). Butthen there’s Christopher’s friend in season 1, Brendan, who’s basically like him with all his negative traits dialed right up.
He’s a more irritating Chris, and he’s supposed to be, feeling a little stupider, more reckless, and, ultimately, more disposable, since he’s only around for a handful of episodes before becoming one of the show’s earlier fatalities.He had it coming, and might well have been genuinely painful had he stuck around longer… or, like Christopher, there’s a small chance he might’ve been humanized or reworked in some way where many of his flaws became darkly funny or entertaining somehow.
7Fran Felstein
Appeared in 1 episode
Even whenThe Sopranoswas at itsworst, it was still a pretty good show, and that goes for the somewhat infamous season 5 episode, “In Camelot,” which is the only one to feature Fran Felstein. So it says something about the sort of impression she makes that she’s worthy of being counted here, when it comes to irritating or otherwise anxiety-provoking characters fromThe Sopranos.
She’s an old mistress of Tony’s long-deceased father, Johnny, and Tony forms something of a bond with her,since she’s a link to his father in a somewhat unconventional (and, typical for the show, dysfunctional) way. She’s kind of intense and a bit off, from the start, and there’s already some level of weirdness to her spending time with Tony… but then she sings “Happy Birthday” in a way that’s supposed to mirror Marilyn Monroe, and everything goes to hell. It’s a candidate for the title of the single most uncomfortable scene in any episode of the show’s run.
6Matthew Bevilaqua and Sean Gismonte
Appeared in 6 and 4 episodes, respectively
Two annoying characters for the price of one, Matthew Bevilaqua and Sean Gismonte are largely inseparableand, in season 2, sort of fill a similar role to Brendan in season 1. Admittedly, they’re not exactly the same, though, since even though they’re associated with Christopher, they’re both aggressively desperate to impress him to move up in the mob world.
When that doesn’t seem to be working out, they betray Chris and try getting on the side of Richie, misreading the whole situation and sealingtheir fates when they attempt to kill Chris, thinking it’s what Richie wants.Their characters and violent endsare used to drive home the idea of it taking time to become a made guy, and the rejection that comes when people try to force or rush their way into “that thing of theirs.”
5Richie Aprile
Appeared in 10 episodes
Richie Aprile has been mentioned often enough before this point, so it’s only fitting to give him an actual placement on this ranking. He bursts into the show with absolutelyno chill at the start of season 2, being established within the mob life, sure, but being out of step due to a lengthy stay in prison. He feels like he’s being mistreated and overlooked by Tony, and this causes him to lash out in increasingly intense ways.
He’s sort of the central antagonist in season 2, and has fewer redeeming qualities than Junior by a wide margin (and he was, arguably, pretty close to the central villain in the first season). He’s generally terrible in pretty much every scene he appears in, but works to raise the stakes as a more outwardly violent villain than the show had had before. Also,the way he exited the show was awesome.
4Livia Soprano
Appeared in 24 episodes
It’s impossible to talk about tyrannical and wonderfully irritating characters inThe Sopranoswithout a shoutout to the most nightmarish of matriarchs herself: Livia Soprano. She’s only a real presence in the show’s first two seasons, owing to thecharacter’s actress,Nancy Marchand, passing awayin real life, but she’s one hell of a thorn in Tony’s side, and continues to haunt both him and the show at large followingher sudden (and surprisingly emotionally complex) exit.
Livia was ahead of her time, because she’s basically what would now be called a troll;put another way, she elevates bullying and being overbearing in mortifying ways. She’s unbearable, sure, but Livia is also kind of hilarious, and might well be oddly likable because of how much she brings to the show. Make no mistake, that likability is not conventional, but, like with Janice,The Sopranoswould’ve been a weaker show had Livia not been a part of it.
3Phil Leotardo
Appeared in 30 episodes
Just as Livia was the ultimate foil to Tony in the first couple of seasons ofThe Sopranos,Phil Leotardo is basically a living nightmare for him in the last couple of seasons of the show. After the likes of Richie, Ralph, and various other minor antagonists, Phil emerges as perhaps the most dangerous and threatening, since he does act in a way that starts a genuine war between the New Jersey and New York crews (a brief one, but still).
He is also an undeniable d**k. Phil is the grumpiest, pettiest, and most vindictive character in a show filled with people who could be described in such a way, and this makes him immensely hateable. He does contribute to the showgetting darker as it approaches the endbut, this beingThe Sopranos, things aren’t that simple, and he’s also an oddly hilarious character at times. Some of his negative qualities enhance the drama, but some of his flaws are played for laughs (“20 years in the can,” “Turn that off!”, “Whatever happened there?”, etc.).
2Jackie Aprile Jr.
Appeared in 11 episodes
Jackie Aprile Jr. is kind of the worst, or, actually, the second-worst, and he only gets a little by way of (extremely mild) forgiveness because he’s young, and that can excuse a little of his immaturity… but certainly not all of it. He’s impulsive, continually idiotic, and shockingly lastsuntil the very end of season 3, after spending the better part of that season just making a mess of everything he breathed in the vicinity of.
Somehow, he also manages to charm Tony’s daughter, Meadow, for a little while, but maybe she gets the benefit of the doubt for also being young and immature at that point.Jackie Jr. is, to reiterate, kind of the worst, after all. He’s also one of those rare annoying characters who’s irritating while also not being unconventionally entertaining or hilarious; things you could, debatably, say about the likes of Phil and Livia.
1Ralph Cifaretto
Appeared in 20 episodes
Unlike Jackie Jr., Ralph Cifaretto is older and should know better, but acts even more recklessly than his fellow season 3 agent of chaos (and Ralph sticks around for most of season 4, too). Richie and Phil were also sociopathic and ruthless, but when Ralph was at his most impulsive, he proved capable of arguably greater evil, as anyone who’s seen the brutal season 3 episode, “University,” can probably attest to.
Ralph does create some compelling drama andJoe Pantolianogives the role his all, to the extent that he can be entertaining to watch, but it’s a guilty sort of entertainment value. Ralph is pure evil, and the fact that he gets away with being evil for so long is what makes him kind of annoying on top ofbeing a love-to-hate sort of character.When it comes to the quality and quantity of viewer frustration caused, no one else in the show hits as uncomfortably hard as Ralph Cifaretto.
