The Sopranos: 10 Saddest Character Deaths, Ranked

The Sopranos may have offered a nuanced look at life within the mob, but it never shied away from reminding audiences of the often fatal consequences of organized crime. Death was very much a part of life on the show, adding a certain level of unpredictability to the unfolding events on screen.

Beloved characters came and went with alarming frequency. Sometimes they were collateral damage in the show’s ongoing turf wars. Other times they ended up in the cross-hairs of Tony himself. Whatever the circumstances, parting was such sweet sorrow for the show’s fans. Here are the saddest character deaths on The Sopranos.

Livia Soprano

Few fans would have mourned the death of Tony’s abusive and hateful mother Livia early in the third season of The Sopranos. However, her sudden passing following a second stroke left Tony struggling with a lot of unresolved feelings. Especially as it was his mother who previously gave the order to have him taken out.

Her demise saw Tony fail to achieve any form of closure. They never made peace. For that, alone, Livia makes this list. The fact that her exit was a result of actress Nancy Marchand succumbing to lung cancer lends it an added layer of emotional resonance.

Tony Blundetto

Tony Blundetto’s journey is tragic because, to borrow The Godfather Part III parlance, he tried to get out, yet they pulled him back in. Tony B’s misfortune began long before the events of the show – he winds up doing a 17-year stretch behind bars for an armed hijacking Tony Soprano was supposed to be involved in.

Left to rot behind bars, Tony B tries to go legit with work as a massage therapist upon release, but his desire to earn money and respect sets him on a dark path of unsanctioned hits and, ultimately, his own demise at the hands of Tony S.

Tracee

The Sopranos hesitated in depicting the dark side of organized crime. Nowhere was that truer than at the Bada Bing and in the case of Tracee. A 20-year-old mother-of-one working in the club to pay off expensive orthodontic work, she quickly strikes up a friendship of sorts with Tony, at one point turning to the Mafia boss for advice about a surprise pregnancy.

But her fate is sealed by the continuation of an abusive relationship with fellow Capo Ralph Cifaretto, who ends up taking her life after she dares to stand up to him following yet another verbally abusive barracking.

Vito Spatafore

Vito Spatafore had a small but powerful role to play in The Sopranos, coming to the fore in the show’s later seasons. A subordinate of Tony Soprano, for much of the show’s run he’s something of a bit-part player, on hand to dispatch the organization’s distinct brand of justice.

He only takes centre stage once it emerges he is a closeted homosexual – something that is deemed unacceptable in certain quarters of the Mafia. Soon on the run, in search of a new life, Vito meets his end at the hands of the homophobic Phil Leotardo and his associates. It’s another grim eye-opener.

Gloria Trillo

Tony Soprano is haunted by many ghosts throughout his time on The Sopranos, but few are as tormented as Gloria Trillo. A fellow patient of Dr. Melfi, Tony is warned against dating her because of her severe emotional issues but selfishly presses on regardless.

A man used to having women at his beck and call, as and when he wants them, Tony soon recoils from Gloria when he becomes aware of her possessive and obsessive tendencies. Tendencies that see her threaten to contact his wife. It’s all the more heart-breaking that, despite his various threats, Gloria ultimately ends up taking her own life.

Sal ‘Big Pussy’ Bonpensiero

From the moment he was arrested at a card game run by family capo Jimmy Altieri, there was an inevitability about Pussy’s fate. Having decided to serve as an FBI informant in exchange for a reduced sentence, Salvatore spent much of the second season of The Sopranos evading the suspicions of his fellow mobsters.

But somewhere at the back of his mind Tony always knew – he just didn’t want to take out his friend. It culminated in an emotional final confrontation, with Tony, Silvio, and Paulie saying goodbye to Pussy aboard the latter’s boat before leaving him sleeping with the fishes. 

Bobby Baccalieri

Nice guys are few and far between on The Sopranos, but Bobby Baccalieri comes closer than most. A big-hearted bear of a man, Bobby may come in for mockery for his size but he was honest, reliable and had no problem holding his own in a fight – as Tony found out after a disagreement over a game of Monopoly.

Bobby remained faithful to his wives too and didn’t whack anyone until late in the show’s run. His sad demise at the hands of Phil Leotardo’s crew was brutal and gut-wrenching, coming moments after tracking down a beloved vintage train set.

Christopher Moltisanti

Christopher wasn’t as loveable as Bobby Baccalieri but he was one of the most human of all of Tony’s crew. He was a hothead. He had flaws. He did some very bad things. But there was also a vulnerability there and sense he aspired to more away from the mob.

That notion shone through during his infrequent forays into the world of Hollywood as a writer and on-set consultant. But it was Christopher’s battles with addiction that painted him in the most sympathetic light and sealed his fate with Tony after one too many drunken mistakes for his uncle’s liking.

Adriana La Cerva

Like Pussy before her, Adriana seemed destined for the grisly end from the moment she got involved with the FBI as an informant. But the skill of the writing behind The Sopranos meant fans were left waiting and hoping as things played out. Maybe she would find a way of playing off both sides against each other? Perhaps Chris would understand when she told him the truth?

Even as Silvio drove her off towards Interstate 287 to meet the apparently hospitalized Christopher, viewers hoped for a last-minute reprieve or sudden twist of fate. But it never came and deep down you knew it never would.

Tony Soprano

Some may still be in denial, given the open-ended nature of that ending but, in their heart of hearts, they must know that Tony sleeps with the fishes. As Bobby notes during a conversation about meeting your maker at the hands of a fellow mafioso: “probably don’t even hear it when it happens, right?”

Even so, all of us hope somehow that Tony Soprano lives on. That he wasn’t taken out, in front of his family, with half an onion ring in his mouth. That would be depressing and strangely undignified. Yet, in a show about the realities of organized crime, it’s just about right.