The Sopranos: the most eccentric, manipulative and downright sociopathic characters

My viewing companion and I have just finished watching The Sopranos. It’s a brilliant series, albeit packed to the gills with death and bloody violence, and of course that ending. As you might imagine from a show about mobsters, everyone is pretty much out for themselves; more than that, however, some of them are just downright emotionally manipulative borderline sociopaths. In this article, I run down some of the worst offenders.

Anthony “AJ” Soprano Junior

At the start of the series, AJ is a fat kid with an impressive appetite and possible ADHD. Compared to his brilliant sister Meadow, he’s a lazy, below average disappointment of a kid, whose delicate stomach and lack of killer instinct mean he’ll never succeed Tony as the head of the family.

Even so, by the time he’s in his late teens and early twenties, AJ has certainly inherited a fair amount of his parents’ selfishness and manipulative ability. Whilst there’s no doubt that he’s genuinely suffering from some emotional problems, he nonetheless manages to get full mileage out of a diagnosis of depression, using it any time someone calls him on his behaviour. Every week he has a different career plan – anything from running a club to joining the army and then becoming Donald Trump’s personal helicopter pilot – and according to him, the only thing holding him back is the fact that his parents won’t help him get started.

Amongst his friends, AJ is happy to play the “Tony Soprano’s son” card when there’s respect or material gain to be had, but he never uses his influence for good. When his companions beat up a Somali boy, AJ stands back, but he makes no move to stop them. Later, in counselling, he bemoans how everything in the world is terrible and there’s no point to anything, but he lacks the strength to do even the things within his power to change that.

Livia Soprano

Livia Soprano is the perfect example of how our parents can really fuck us up. She is the archetypal Italian mother taken to an extreme – always disappointed by her children and disapproving of the world she lives in. When she’s not bemoaning her life or reminding everyone that her deceased husband Johnny was “a saint”, Livia’s words are chosen for maximum cutting effect, and she rarely fails to draw blood. In the guise of commiserating with Artie over the fire at his restaurant, she just happens to let slip that Tony was responsible. Later on, she even conspires with Junior to kill her own son.

Livia isn’t above using her age to her advantage either. Although it’s possible she really is descending into senility by the end of her life, there’s no doubt that there are times she’s just putting it on to make life difficult for Tony. You can never be quite sure what she’s thinking, only that it will end badly for someone.

Janice Soprano

Janice is the character everyone loves to hate. She’s the kind of person who would trip you over at the top of the stairs, and then sue you for injuring her ankle. More than anyone else in the series – and that is saying something – Janice is out for Janice, and no one else.

Like her mother, Janice has a talent for saying seemingly innocent remarks with a hidden agenda. She manipulates people as easily as breathing, and, when called out on it, feigns upset at being accused of ulterior motives. Janice even goes as far as stealing Svetlana’s prosthetic leg in order to blackmail her nto giving up her entitlement to Livia’s record collection.

As someone who hates work and gainful employment, there’s very little Janice won’t do to ensure a free ride for herself. After the death of Bobby Bacala’s wife, she sets her sights on a cosy life with him, and manages to manipulate herself into becoming his second wife. Even then, she has little interest in doing her share of the chores and childcare.

Irina Peltsin

Tony had many mistresses, or “goomars”, over the course of the series, and not all of them were very mentally stable. Take Irina, the first girlfriend we see on screen. Tony was never going to leave his family for her, and yet she didn’t quite get that; in fact, she threatened to kill herself when he broke up with her. Later, when Tony starts sleeping with her cousin, she ruins the happy Soprano home for an entire season by telling Carmela all about Tony’s indiscretions.

Elliott Kupferberg

As Melfi’s therapist, Elliott’s job was to sit and listen to what she had to say, and counsel her appropriately. Instead, he often ended up telling her what to do – especially when it came to the matter of Tony Soprano.

For most of the series, Elliott is just a minor arsehole in the grand scheme of things, but as the show draws towards its finale, he ramps it up a bit. First, he deliberately draws Melfi’s attention to a study that shows that criminal patients often use talk therapy as a way to hone their skills. Having sowed the seeds of doubt in her, the topic then comes up again at a dinner party, in which Elliott completely and utterly breaches confidentiality by letting slip that Melfi has been Tony’s therapist all this time. One could even argue that he is the reason that Melfi decides to stop seeing Tony as a patient.

Paulie Gaultieri

Oh Paulie, Paulie, Paulie. In some ways, he might just be the most eccentric and psychopathic character to grace The Sopranos. Paulie is paranoid, vindictive, easily upset, and all too keen to resort to violence. A master of insensitivity, if there’s something outrageously tactless or inappropriate to be said in any given situation, Paulie will say it.

Although his loyalties have wavered on occasion, for the most part he is fanatically devoted to Tony – to the extent that he defied orders to burn a painting of Tony with his racehorse, instead getting Tony repainted in a general’s uniform and hanging it on his wall.

Upon finding out that the woman he thought was his aunt is actually his biological mother, he immediately becomes enraged with his adoptive mother, accusing her of taking advantage of his love. Not a man given to empathy, Paulie only ever sees things from one perspective – Paulie’s.

Richie Aprile

Even by Sopranos standards, Richie Aprile is a nasty bit of work. As soon as he is released from prison, he begins a rampage of bloody violence, starting with ramming his former partner with a car and then running him over once more for luck.

It’s this kind of behaviour that characterises Richie throughout his time on the show. Even when he’s trying to be conciliatory, all it takes is one little thing to rub him the wrong way, and suddenly someone’s getting hurt. He meets his end at the hands of his fiancée Janice Soprano not a moment too soon.

Tony Blundetto

When Tony Blundetto gets out of prison, he does at least try to live an honest life – his plan is to forget his mafia past and open a massage parlour. Unfortunately, it just doesn’t last – before too long he’s in debt, beating women and killing people for money.

Back when he and Tony were younger, Blundetto was basically that kid at school who was always telling off-jokes and playing dubious pranks. It seemed funny at the time, but flash forward to the present day, and he’s still doing it, even though everyone else has grown up and is bored of his antics. Ultimately, it’s inevitable that he manages to make such a mess of things that he incurs the ire of not one, but two crime families. And since two Tonys turn out to be too many, it’s up to Tony Soprano to resolve the situation by taking him out of the picture.

Ralph Cifaretto

When you reach the end of season two, it seems impossible to imagine that there will be a worse character than the unpredictably violent Richie Aprile. But Richie pales into nothingness once Ralph comes along.

Right from the start, Ralph is irritating, obnoxious and insubordinate. He elevates casual insults to a fine art, even going so far as to earn the wrath of Johnny Sacrimoni by making a joke about his wife’s weight. Pretty much everyone wants to see the back of Ralph, but he manages to get away with his behaviour because he’s such a good earner.

Ralph takes it to another level when he gets a stripper pregnant and then beats her to death. It’s not this that seals his fate, however; that happens when he desperately needs cash for his son’s operation. The required money comes in the form of an insurance payout when Ralph and Tony’s racehorse suddenly dies in a mysterious stable fire. As we all know, Tony can get very attached to animals, and this is enough to send Tony round to Ralph’s for an angry and violent confrontation. It doesn’t end well for Mr Cifaretto, but none of us are sad to see him go.

Gloria Trillo

Gloria Trillo isn’t Tony’s usual type of girlfriend. She’s not young, naive and in the thrall of a powerful mob boss – she’s older, poised and rich enough to be able to buy Tony gifts. That being said, she has a set of issues all her own.

Gloria loves flirting with danger. She deliberately befriends Carmela just to push Tony’s buttons, and seems to like it any time his temper is raised. Not that she doesn’t play the anger card herself sometimes, at one point even flinging a plate of steak at Tony’s head. She enjoys provoking and manipulating Tony, to the extent that he realises that his interactions with her echo the fractious relationship he had with his own mother.

Sadly, Gloria is a deeply troubled person, and even the ministrations of Dr Melfi can’t help her – some time after Tony ends their relationship with a vicarious death threat, she takes her own life.

Phil Leotardo

Phil Leotardo isn’t a man you want to cross. He’s a man with some serious emotional baggage – why else would he be so upset that his family’s surname has changed over the years from the venerable ‘Leonardo’ to the less impressive ‘Leotardo’?

When Phil is angry with someone, they tend not to live long. He threatened Lorraine Calluzzo by staging a mock execution, only to end up killing her later on anyway. Phil obsessively pursued a revenge killing of Tony Blundetto, in which he intended to capture and torture Tony once he got his hands on him. Tony Soprano was forced to kill his own cousin just to spare him the likelihood of a lingering and painful death. Naturally, Phil wasn’t happy to hear about Blundetto’s death at the hands of someone other than himself – if anything, he was angrier than ever to have been denied his personal vengeance.

As Phil rose to power in the Lupertazzi family, he became ever more difficult to deal with. Disgusted by any action he considered weak and effeminate, he became obsessed with killing Vito after learning that Vito was a closet homosexual. When Phil finally caught up with Vito, he had his men not only kill him, but shove a nightstick up his backside.

As the series draws to a close, tensions between Tony and Phil only continue to rise, and the situation escalates. Ultimately, Phil decides to put a hit out on Tony, Bobby and Silvio, before going deep into hiding. After a long and bloody back and forth that costs Bobby his life and sees Silvio put into a coma, Phil is finally taken out – not only is he shot, but his SUV subsequently rolls over his head.

Christopher Moltisanti

Objectively, Chris is not a nice person. He’s violent and impulsive and quick to provoke his allies. Right from the start, he flouts authority, gets people’s backs up, and even finds himself the target of a mock execution – just a prelude for the time he actually does get shot.

We see him hitting his first fiancée, Adriana, and generally being an arsehole to her – even blaming her when he’s the one in the wrong. When he finds out that she’s become an FBI snitch because they threatened her with a prison sentence, he even orders a hit on her. In his opinion, why couldn’t she just have done the five years in prison?

All that being said, as the series progresses, you find yourself starting to like Chris. Whether he’s at odds with Paulie or battling his heroin addiction, you want Chris to succeed. You start to feel a bit sorry for him, desperate as he is for Tony’s approval, and surrounded as he is by peer pressure to fall off the wagon.

When Christopher marries Kelly and fathers a child, you want to think of it as a fresh start for him, but of course he can’t keep it up. “Oh, Christopher”, you sigh, as he takes heroin with his goomar. Of course it doesn’t end well. Christopher crashes his car whilst high, and instead of getting him prompt medical attention, his passenger Tony decides to end his suffering.

Tony Soprano

In the very first episode, we get a sense that there is more to Tony than just a standard, heartless mob boss. After all, he has panic attacks and has to go to therapy – not to mention how upset he felt when the ducks living by his pool up and leave.

From there, it’s easy to spend the next six seasons waiting for Tony to get in touch with his emotional side, to reveal that, deep down, he really is a good person. And yes, through his dreams and hallucinations, we know that there are things that trouble him – that he really is haunted by the ghosts of the people he killed. Even so, as we get to the end of the series, we have to appreciate that he is never going to have that emotional breakthrough.

As boss of the family, Tony has plenty of blood on his hands, both directly and indirectly. Cold-blooded hits, mercy killings, spur of the moment rage – Tony can lay claim to it all. What’s more, in Tony’s eyes he is never wrong, and he never learns from what he has done.

The Sopranos isn’t meant to be Tony’s redemption arc, but for those of us indoctrinated into narrative tropes, we might still expect that on some level. But Tony is never going to turn around and realise the horror of what he has done, or stop doing it. Six seasons after we first make his acquaintance, we see him end the life of his ‘nephew’ and protégé Chris, only to completely deny any guilt or remorse. He was right to do it, because Christopher was a liability who could have killed his own child by driving whilst high. He’s not sad that Chris is dead – he’s downright relieved.

At home, Tony is much the same. In his eyes, he’s never in the wrong, which is why his arguments with Carmela get so heated. His on-again, off-again relationship with therapy demonstrates his reluctance to believe that he could ever have something to learn from it. In his mind, he’s the benevolent provider for his family, and the boss of his Family – and everyone should realise and respect that.

Yes, Tony is the protagonist, and we find ourselves mostly on his side. But we should never make the mistake of thinking that he is a nice person.

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