Ranking The Most Tragic Characters On ‘The Sopranos’

A show like The Sopranos, (available to stream anytime on HBO Now), set in the violent world of the mafia, is bound to have more than its share of tragedy. The world of mob boss Tony Soprano (James Gandolfini) is based on usury, manipulation, intimidation, and murder, and anyone who got caught up in this world was bound to be chewed up and spit out like gum that’s lost all its flavor. Some of those who ended up discarded were lucky to walk away with nothing, where others weren’t able to walk away at all. Here are the 10 most tragic characters in Sopranos history.

10) ‘Pussy’ Bompensiero

Thanks to some well-timed food poisoning and a night of fever dreams, Tony realized what needed to be done after spending the better part of a year wrestling with the possibility that his associate and best friend, Sal ‘Big Pussy’ Bompensiero (Vincent Pastore), was talking to the FBI. Tony, Silvio, and Paulie (Tony Sirico) lured Bompensiero onto a boat in the middle of an ocean and, after a round of tequila shots, killed him. Knowing what was in store, Pussy even broke down and begged for forgiveness, going on and on about how he used disinformation in a desperate, last-ditch attempt to keep himself alive. It wasn’t enough, and in the end, they didn’t even let him sit down.

9) Junior Soprano

It’s easy to write off the human side of a character like Corrado ‘Junior’ Soprano. He was manipulated by Tony’s own mother, Livia (Nancy Marchand), into killing her son, and after a brief reign as boss, he ended up behind bars by the end of the first season. Later, he was placed under house arrest, and spent the rest of the show slowly withering away inside his wood-paneled walls.

Even after (sort-of) making amends with Tony, his mind gradually decayed to the point where he tried to kill him a second time, and spent his few remaining days in a run-down state mental hospital devoid of any real idea of who he was. He might not have been the most likable guy, but his life ending like that is enough to make even Tony shed a tear.

8) Vin Makazian

A police detective who had a side job as Tony’s personal private investigator, Vin Makazian provided valuable information that afforded him some leeway with his gambling issues. He never could quite get his life in order, but he was nonetheless a valuable commodity to Tony, even though Tony showed it by mercilessly berating him, calling him a “degenerate gambler with a badge,” only to turn around and placate him when he’d gone a little too far.

When he was busted in a prostitution raid with a few members of Tony’s crew, Vin couldn’t bring himself to add “disgraced cop” to his resume, and he decided to end it all. His death may have had little impact on Tony, though the information that died with him proved to be devastating, which didn’t help Tony’s slide into a deep depression.

7) Vito Spatafore Jr.

After his father’s public outing, prolonged absence, and then brutal murder, Vito Spatafore Jr. (Brandon Hannan) ended up harboring quite a few issues — and understandably so. He fancied himself a goth kid, wore black-and-white makeup, and, when bullied by classmates, he retaliated in very extreme ways. Both his uncle, Phil Leotardo (Frank Vincent), and Tony even tried to have heart-to-heart talks in an attempt to help. Seeing no other option, his mother, Marie (Elizabeth Bracco), begged Tony for enough money so she and her kids could simply move away, giving them all a chance to start over far from the shadow that the mob cast over their lives.

Had Marie asked Tony on a different day, things might have worked out that way, instead, she caught Tony amidst a particularly bad losing streak, and he offered up a cheaper alternative: send Vito Jr. to a child boot camp. Not seeing any other option, Marie agreed, and in the middle of the night, two men came into their home and dragged her son screaming into their van before driving off. Pretty rough ending for a once-normal kid whose life ends up ruined by circumstance.

6) Davey Scatino

Davey Scatino (Robert Patrick) was a small-time gambler who probably spent a little too much time at Richie Aprile’s (David Proval) card games, but it was when he tried to leverage his longtime friendship with Tony that he not only ruined his life but his family’s lives too. And after running up a $50,000 debt to his former friend, Davey learned very quickly that his years of history with Tony meant very little.

To recoup the money he owed them, Tony and company descended on Davey’s sporting goods store, running up his credit for bulk orders of everything from barber scissors to airline tickets to sell on the black market. As a result, Davey’s personal life fell apart, he alienated himself from his wife and son, contemplated suicide, and after he was left with nothing, left New Jersey in hopes of starting over out west. While his world was crashing down around him, it was just another run-of-the-mill business transaction for Tony and his crew.

5) Tracee

One of the show’s most heartbreaking deaths, Tracee (Ariel Kelly) was a single mother from a broken home who owed money to her boss, Silvio (Steven Van Zandt), and ended up pregnant with Ralphie’s (Joe Pantoliano) kid. Regardless, in her own clumsy, misguided way, she tried her best to make a normal life for herself, but in that environment, her tragic ending seemed to be all but inevitable.

While he did his best to distance himself from her while she was alive, Tracee’s (brutal) death had a profound impact on Tony that went way beyond the feud it started with Ralph. He mentioned her death in therapy (folded into a lie, which wasn’t unusual for him), and was reminded of her weeks later when trying to make amends with his daughter, Meadow (Jamie Lynn Sigler). For a character who only appeared in a single episode, her abrupt end has a real emotional weight to it that was not easily forgotten.

4) Tony Blundetto

After serving close to 20 years behind bars, Tony Soprano’s cousin, Tony Blundetto (Steve Buscemi), wanted nothing more than to start his life over. Despite what his cousin had planned for him, Blundetto tried to go straight, working long days delivering laundry and long nights trying to get his small business off the ground. While he wanted the best for him, Soprano couldn’t help but gloat a little bit when it became clear that Blundetto couldn’t seem to make it work, smugly reminding him that “it’s hard to do business with strangers.”

Still, even after Blundetto abandoned all hope of going straight and his cousin’s repressed guilt opened up some career opportunities, he still believed that he needed to do more for his twin sons. With the promise of a hefty payday, he involved himself in a New York family’s civil war. After taking matters into his own hands, he ended up setting in motion a chain of events that made his violent end just one more tragic inevitability that Tony Soprano had to deal with.

3) Vito Spatafore

The storyline about Vito Spatafore (Joseph R. Gannascoli) being outed as a gay man after lying to himself his entire life to avoid being ostracized (or worse) by those around him is one of the shows more heavy-hearted subplots. Once he’s spotted at a gay club by two associates making a collection, Vito hides out in a small New Hampshire town. While there, he longed for his wife and kids but managed to briefly live out the kind of life he had dreamed of.

Alas, it’s a fleeting moment, and as Vito realized he wasn’t cut out for small-town civilian life, he went back to New Jersey to try and piece his life back together. Of course, his effort is all in vain, and Phil Leotardo has Vito tortured, sodomized, and beaten to death in a cheap motel room. The hard truth of this one is that Vito’s sexual orientation wound up being enough to warrant his killing in the eyes of some in the underworld, something that an increasingly tolerant Tony has trouble accepting. The fact that it was done so violently (even by the mob’s standards) was both a hateful act of prejudice and an excuse for Phil to flaunt his power in front of Tony.

2) Meadow Soprano

It may have seemed like Meadow Soprano was doing pretty okay at the end of The Sopranos‘ run; she’d graduated from law school, was offered a job at a prestigious law firm with a six-figure salary, and was in a relationship with the son of a longtime family associate.

But looking back a bit, her overall story is layered with tragic undertones. When she was still in high school, she confronted her father directly about him being in the mafia, who then spent their entire road-trip together tracking down — and killing — a former associate. The night before she graduated high school, she walked in the door to find him being arrested in their home, a recurring sight that has a huge influence on her. Then, Tony’s racist attitude toward one boyfriend, Noah (Patrick Tully), ended up costing her her first real relationship, and the next guy she dated, Jackie Jr (Jason Cerbone), ended up dead. Even her college boyfriend, Finn (Will Janowitz) got pulled into the underworld enough times to be scared off of the Soprano family for good.

Top this all off with the fact that her inability to properly parallel park caused her to miss out on the best onion rings in the state, and that she may have very well witnessed her father being murdered in cold blood, (or possibly the whole family, depending on what theory you subscribe to), and it doesn’t seem like Meadow really managed to come out ahead here.

1) Adriana La Cerva

Out of all the characters on The Sopranos, just about every one of them had some kind of hidden agenda. All of them except Adriana (Drea De Matteo), the blindly loyal fiancée to Christopher (Michael Imperioli) — who was a tragic character in his own right.

All Adriana really wanted out of life was to be with Christopher, but after years of talking to the FBI, they ended up catching her trying to help cover up a murder. Facing a hefty prison sentence should she not cooperate, they demanded she wear a wire, but they let her go to try and convince Christopher to testify against Tony. With everything going wrong, Adriana still believed that she’d be able to start a new life with Christopher “away from all this sh*t.” For a little while, it even seemed like it might work out. That is, until it was revealed that she’d been tricked into thinking Christopher had attempted suicide and she was driven out to the middle of nowhere and gunned down by Silvio.

In the end, no character’s death managed to leave a void as devastating as Adriana’s. She haunted Carmela’s (Edie Falco) dreams, Christopher would talk about her to his new wife, Kellie (Cara Buono), and her mother, Liz (Patty McCormick), crawled further into the bottle, certain of her daughter’s fate and powerless to do anything about it. With Adriana gone, there was no more innocence, no more wide-eyed idealism, and no more heart. Just characters who worked tirelessly to lie, cheat, and undermine one another, simply because it was business-as-usual.