The Most Devastating Deaths On The Sopranos

There's no question that "The Sopranos" is one of the greatest television shows ever. In six seasons on HBO, the saga of Tony Soprano and his families (his Mafia crime family and his actual family) shocked and engaged audiences. Tony set a blueprint for the many antiheroes in the late '90s and early 2000s who were compelling characters but were never presented as virtuous or heroic. Tony was perhaps a tad less psychopathic than some of his colleagues and enemies, but he was presented as a violent sociopath from the very beginning. 

Violence on "The Sopranos" was never glamorized. It was ugly and demeaning, and that was especially true when someone was killed. Death was a constant in the life of Tony and his gang, either in dealing it out or having it dealt to them. At the same time, "The Sopranos" examined death from a number of angles that included disease, old age, and just plain bad luck.

Let's take a look at the most devastating deaths on "The Sopranos." Some of them were mob-ordered hits, some were born out of rage or desperation, some were ridiculous, and some were people succumbing to painful natural deaths. Some of the deaths made it to the list because they were especially humiliating or upsetting.

John "Johnny Sack" Sacrimoni (Vincent Curatola) was the head of New York's Lupertazzi crime family and usually a close ally of Tony Soprano. They weren't exactly friends, but both were usually the cooler heads that prevailed for the sake of peace and expanding "business."  At one point, he nearly started a war out of sheer outrage when a member of Tony's crime family insulted his beloved but overweight wife Ginny with a tasteless fat joke. That conflict was averted, but another one started when Tony's cousin Tony Blundetto killed the brother of Phil Leotardo, one of Johnny Sack's capos. Just when that crisis was defused, Johnny was arrested by the FBI, who had reams of evidence on him thanks to an informant.

Johnny didn't flip and become a rat himself, but he did plead guilty and perform an allocution, which included admitting that the Mafia existed — a huge breach of Cosa Nostra protocol. He did this in part to get a reduced sentence so he could get out and still be young enough to enjoy his life and his grandchildren, but fate had a way of playing a cruel trick on him. Years of smoking led to advanced lung cancer, and he died in a prison hospital. The mundane nature of his death made it all the more relatable, as it reaffirmed that mob figures weren't invincible. He died in Season 6, Episode 14, titled "Stage 5."

Richie Aprile (David Proval) was the brother of Jackie Aprile, who was head of the DiMeo crime family when the series started. Tony eventually became the de facto boss when Jackie died, although he positioned his uncle Junior (Dominic Chianese) as the nominal head. Richie was in prison for 10 years when all of this was happening, so when he re-emerged, things were much different than he remembered. He resented Tony as the boss, seeing him as the young guy who had to buy him dinner and take orders from him.

Moreover, Richie made the other mobsters look like cultured, calm gentlemen. Violence was his only solution to virtually everything. Another complicating factor was that Richie started dating his old flame Janice Soprano (Aida Turturro), Tony's older sister. The scheming and power-hungry Janice would needle Richie about Tony, urging him to make a move to take over the family. But what looked like it would become a deadly power struggle between Richie and Tony had a shocking ending. 

After Richie and Janice got engaged, they got in an argument as Janice defended Richie's gay son Little Ricky. Richie nonchalantly punched her in the head and then started eating dinner. A shaken and enraged Janice grabbed a gun and shot him dead. Tony cleaned up after her and put her on a bus out of town, as two of his biggest headaches canceled each other out. Richie died in Season 2, Episode 12, "The Knight In White Satin Armor."

"Jackie Junior" (Jason Cerbone) was living proof that brains and cunning did not necessarily run in the family. His dad was a beloved and respected crime boss who was smart enough to know that his son wasn't cut out for the family "business" and encouraged him to go to college. After he died and his uncle Richie got out of prison, Jackie Aprile Jr. started gravitating toward mob life, even though he was thick as a brick.

After Richie died, Jackie Junior seemed to turn his life around, until his mother Rosalie started dating the truly vile Ralph Cifaretto. Jackie Junior started dealing drugs just as he started dating Tony's daughter Meadow (Jamie-Lynn Sigler). Tony had promised Jackie Sr. that he'd look after his son, but Jackie Junior was selling and using drugs, and Meadow dumped him when she found out he had slept with a sex worker.

Jackie Junior assembled his own young crew even dumber than he was and tried to rob a card game run by one of Tony's men. He did it partly because his dad and Tony had done something similar when they were kids. Of course, Jackie panicked and killed the card dealer when he realized he had been identified and went into hiding.

After some deliberation, Tony had Vito Spatafore shoot Jackie Junior in the back of the head in Season 3, Episode 13, "Army Of One." Naturally, Tony blamed the killing on Black drug dealers — but Meadow knew better.

Phil Leotardo (Frank Vincent) was another mobster who was released from prison during the course of the show. He served a 20-year sentence and went back to work for the Lupertazzi family and Johnny Sack. Leotardo had a veneer of respectability, but he was a brutal killer and sickening homophobe. He nearly started wars with Tony Soprano several times over various offenses related to business and his men getting killed or beaten. That included him wanting to kill Tony's cousin Tony Blundetto and one of Tony's soldiers, Vito Spatafore. 

After yet another conflict, Leotardo got the go-ahead to kill Tony and his top men. After Tony evaded him, he negotiated with Leotardo's disgruntled captains and got their permission to kill him. Leotardo was the last onscreen death of the entire series, occurring during Season 6, Episode 21, "Made In America." Tony's men spotted him at a gas station and shot him, with the car running and his grandkids in the back seat. What made the scene particularly horrifying was that the car lurched forward and crushed Leotardo's skull, rendering him unrecognizable.  

Ralph Cifaretto (Joe Pantoliano) was the single most grating character on the show. His smart mouth and vicious streak meant that he always had a cutting remark at the ready. He was the ultimate example of how a mob leader like Tony had to weigh business utility against personal interactions, because Ralph was easily his top earner but no one could stand him. Ralph's mouth and temper frequently created problems. His tasteless joke about Ginny Sacrimoni's (Denise Borino-Quinn) weight nearly caused an all-out war. He coldly murdered a stripper named Tracee. He pranked Paulie Walnuts' mother and nearly gave her a heart attack. His bad influence helped lead Jackie Aprile Jr. to his death. In short, Ralph was just the worst and was killed in Season 4, Episode 9, "Whoever Did This."

When one of Ralph's sons nearly killed the other accidentally with an errant and unsupervised arrow, Ralph suddenly needed a lot more money for hospital bills. While he felt horrible about his son, that didn't stop him from burning down the stable that contained a race horse co-owned by Tony and him. When Tony talked to him about it and Ralph more or less confessed to it, Tony went into a rage. What followed was the essence of "The Sopranos" in many way: an awkward, ugly, visceral fight that was uncomfortable to watch. Tony eventually strangled Ralph and slammed his head into the floor to kill him. He and Christopher then spent a long time chopping him up and disposing of the body. 

Lorraine Calluzzo (Patti D'Arbanville) was an unusual character in that she was the rare woman who operated as a member of a crime family. She ran a loan shark business as part of the Lupertazzi crime family. When Carmine Lupertazzi died of a stroke, Johnny Sack became the new boss of the family. However, Lorraine did not recognize his authority and kicked up her money to Lupertazzi's son, "Little" Carmine. 

This did not sit well with Johnny Sack, who gave her one warning when he staged a mock execution. Tony tried to intervene on her behalf with Johnny Sack but to no avail. She continued to ignore Johnny Sack's orders, and he responded by sending over two hitmen. As she stepped out of the shower, the killers chased her naked halfway across the house before mercilessly executing her. It was a tremendously awkward and vulnerable scene, as Calluzzo literally had no defense and not a shred of dignity when she was killed next to her lover. It emphasized and underlined the dehumanization that takes place when a killer makes a hit; she might as well have been a bag of meat. She was executed in Season 5, Episode 6, "All Happy Families..."

J.T. Dolan (Tim Daly) was an example of a civilian who got caught up in the orbit of organized crime and paid the ultimate price. Dolan was a screenwriter who met Christopher Moltisanti (Michael Imperioli) in rehab, and they bonded over their mutual love of movies and writing. Dolan had a weakness for gambling on horse racing and soon found himself in debt to Christopher. When he couldn't pay, Christopher beat him up and took his car.

Later, Dolan went back to rehab and started teaching screenwriting. Christopher had him kidnapped and gave him an ultimatum: either help him write a screenplay for his "Cleaver" film idea or else. If Dolan wrote the screenplay, his debts would be forgiven. Dolan did it, and the film had a successful debut, though Christopher pretended that Dolan had little to do with it. 

Dolan tried to distance himself from Christopher, but the young mobster still thought of Dolan as a sort of friend and artistic confidant. In Season 6, Episode 17, "Walk Like A Man," Christopher started confessing various crimes to Dolan. Dolan just wanted him to shut up and leave, at one point yelling out, "Chris, you're in the Mafia!" as a way to get him to stop talking. Well, it sort of worked, as an alarmed Christopher realized what he was doing and shot Dolan in the head. For Dolan, it was all about being in the wrong place at the wrong time with an unstable addict with severe anger issues.  

Many times on "The Sopranos," it's clear that the mobsters tried to justify and assuage their guilt over being killers by comparing it to being soldiers in a war. If a guy got hit, he knew what the stakes were. If someone disobeyed them or owed them money, they knew what the potential dangers were. However, that façade was paper-thin, as they inflicted plenty of other violence on innocents for no good reason. They were violent men with hair-trigger tempers who solved their problems with blunt force.

A perfect example of this came in Season 4, Episode 12, "Eloise." Paulie Walnuts (Tony Sirico) needed more money in order to keep his beloved mother in a retirement home. When he learned that Minn Matrone (Fran Anthony) was excluding his mother from social activities after his mom nearly killed them accidentally, Paulie was outraged. When he learned that Minn kept her money under her mattress, he set out to solve a cash flow issue and get back at Minn.

When he found Minn at her house after thinking she'd be away, she threatened to call his mom and kicked him. He took her down and suffocated her with a pillow in a brutal, ugly scene. For a character who had provided a lot of comic relief in the show's run, this was a shockingly repellent scene that he gleefully embraced because it solved a number of his problems. 

Sometimes, the illusion of freedom is far worse than being resigned to a lifetime of servitude. Such was the case for Eugene Pontecorvo, a loyal soldier of Tony Soprano who was given a life-changing amount of money by a dead aunt. It was so much money that he hoped to move to Florida with his wife and kids and retire from mob life. He gave Tony a taste of the cash and a variety of gifts, in an attempt to buy himself out of servitude. At the same time, it was revealed that he was also an informant for the FBI. They also wanted him to stay, especially since another of their informants had just died.

The problem was that Pontecorvo had counted his chickens before they hatched and assured his wife that Tony would say yes. Even after he was forced to help Christopher Moltisanti with a hit in order to curry Tony's favor, Tony still ultimately said no. He didn't want to lose a useful asset and told Eugene, "You took an oath." His wife was furious and wouldn't accept any kind of compromise. With seemingly no way out, Eugene shockingly went into his basement and hung himself. This took place in Season 6, Episode 1, "Members Only." The scene as shot was long and lingering, as a way of reminding the viewer just how desperate things had become for Eugene. 

Sal "Big Pussy" Bonpensiero (Vincent Pastore) was not only a loyal soldier of Tony Soprano's, he was also a loyal soldier to Tony's father Johnny Boy. He was a beloved, jovial figure in the crew and a family man with an even temper. Indeed, he loved his wife and kids so much that he started to live outside his means and launched a sideline of selling heroin. He did this against the advice of Jackie Aprile, Sr., given its risk. Sure enough Big Pussy was caught and arrested. Facing 30 years in prison, he became an informant for the FBI.

For a long time, he felt conflicted about informing, feeding the FBI as little as possible. A crooked cop in Tony's employ learned that Big Pussy was an informant, but Tony would not act without total certainty. When another member of his organization who bore a resemblance was outed, Big Pussy was seemingly safe for a while. But when Big Pussy was demoted by Tony, he was suddenly more amenable to informing on him. 

Guided by a dream, Tony found a pretext to search Big Pussy's bedroom and found a wire. He then lured his former best friend onto a boat at sea, where Tony, Paulie and Silvio Dante (Steven Van Zandt) shot him after getting him to admit he had flipped. This happened in Season 2, Episode 13, "Funhouse." It was a stunning death because he was the biggest protagonist to die on the show up until that point.

The death of Tony Blundetto (Steve Buscemi) was one of the more painful and significant in the history of "The Sopranos." Known as "Little Tony," he and Tony Soprano were cousins and grew up together. Tony B. went to prison but when he came out, he intended to go straight and get a job as a massage therapist, much to everyone's surprise.

For a while, he did just that, even turning down a job with his cousin Tony in the organization. When working with an outsider started to go sour, Tony B. went back to crime. The problem was that even though he was dealt back in, he didn't advance as quickly as he wanted. He took a contract killing job from associates of "Little" Carmine, shooting an associate of Phil Leotardo. Tony B. denied taking the job but things escalated, as Phil avenged that killing and Tony B. retaliated by killing Phil's brother Billy and wounding Phil.

Phil was out for blood, but Tony Soprano was reluctant to give Tony B. up. That was partly out of love, but mostly out of guilt, as he had lied about what happened the night Tony B. was arrested, saying he was jumped. Ironically, Tony realized this in a therapy session and later confessed it to Tony B. After dealing with a near-revolt from his own men, Tony took matters into his own hands, cleanly killing Tony B. so that Phil wouldn't torture him before executing him in Season 5, Episode 13, "All Due Respect."

Vito Spatafore (Joseph R. Gannascoli) was the quintessential "Sopranos" character: deeply flawed morally yet sympathetic in some ways. Vito was one of Tony's top earners, a family man, and a loyal soldier. He carried out the hit on Jackie Aprile Jr., for example. Vito also had a secret: he was a closeted gay man who sought out public hook-ups and frequented gay bars. For the mob, being gay was almost worse than being an FBI informant until only recently, according to Metro.  

Vito was spotted in a gay bay in full leather regalia by an associate of Tony's. No one quite wanted to believe it and Tony revealed he honestly didn't care what people did behind closed doors. However, Phil Leotardo was out for blood, as Vito was married to his cousin, and Phil was a rampaging homophobe. When Tony sent two of his men to bring Vito in for a little chat, Vito fled to New Hampshire.

In a small tourist town, Vito found refuge. Pretending to be a sportswriter, he struck up a romance with a cook. Though he relished the freedom to be himself, he missed his family and the excitement of the mob lifestyle. Plus he hated actually having to work for a living as a handyman, so he went back to New Jersey.

Phil ambushed Vito and had his men brutally beat him to death in Season 6, Episode 11, "Cold Stones." Phil's sheer exuberance in watching Vito die made this one of the show's most disturbing death scenes.

On "The Sopranos," life was frequently cheap, especially if you weren't part of the mob and a "made man." The tragic story of Tracee (Ariel Kiley) dramatically illustrated this, reminding the viewers that these mobsters were sociopathic killers, not cool guys, even if they pretended otherwise. A dancer at Tony's strip club, the Bada Bing!, Tracee had the misfortune of being involved with the particularly vile Ralph Cifaretto. Tracee had her own problems: she had her baby taken away by child protective services after she burned her, due to anger brought on by years of abuse.

She wanted to quit dancing after she shacked up with Ralph, but she owed money for orthodontia to her boss, Silvio Dante. He literally dragged her kicking and screaming from Ralph's and made her get back to work. She confessed to a sympathetic Tony that she was pregnant with Ralph's kid, and it was clear that he thought of Tracee as a daughter. He advised her to get an abortion despite being a Catholic.

When she told Ralph, he initially seemed happy and promised to marry her but then revealed he was just kidding and said a number of demeaning things to her. When she slapped him outside the Bada Bing! in Season 3, Episode 6, "University," Ralph responded by savagely beating her to death. Tony hit him, violating mob protocol, but Ralph was punished not for killing her but for "disrespecting the Bing." 

Christopher Moltisanti was technically Tony Soprano's cousin, but due to their age difference, he referred to him as his nephew. He was one of the people closest to Tony and a loyal soldier. Unfortunately for everyone, Christopher was also an addict who drifted in and out of heroin and alcohol dependency. When Tony needed someone to do dirty work like disposing of Ralph Cifaretto's body, he'd call Christopher. He literally knew where all the bodies were buried. Conversely, Tony was there for Christopher as well. He urged him to get clean in an intervention and later had Christopher's fiancée Adriana killed when that had to be done. 

What led to his death? An impaired Christopher was driving Tony on a highway and drifted into the wrong lane. He swerved and they flipped multiple times into a ditch. Christopher wasn't wearing his seat belt and was coughing up blood but still alive. However, he begged Tony for help, saying that he couldn't pass a drug test. When Tony saw the baby seat for Christopher's infant daughter pierced by a huge branch, he realized that Christopher was way too much of a loose cannon. As an addict, he was also vulnerable to being flipped by the feds.

Instead of helping Christopher, Tony pinched his nephew's nose and suffocated him. As with many of the show's characters, it was a pathetic ending for a cruel, sad life; even the show's major characters weren't immune. Christopher was killed in Season 6, Episode 18, "Kennedy and Heidi." 

Bobby Baccalieri (Steven R. Schirripa) was the closest thing to a decent human being on "The Sopranos." Ridiculed for his weight and gentle manner, he nonetheless was highly loyal to Junior Soprano and then Tony when he became part of his crew. Bobby was born into this life thanks to his dad, who was a ruthless hitman. Bobby managed to avoid murder for most of his career, making money as a loan shark. He didn't live the kind of fast-paced lifestyle of the rest of the crew and didn't even keep a mistress.

That changed after he married Tony's sister Janice. Bobby's longtime wife Karen died in a car accident and Janice insinuated her way into his life and that of his kids. When Tony and his wife Carmela went on a cabin excursion with Bobby and Janice, Bobby got in a fistfight with Tony and won, defending his wife's honor. Tony resented losing and gave Bobby his first hit assignment, much to Bobby's chagrin.

When Phil Leotardo decided to wipe out Tony's mob, Bobby was one of the targets. In Season 6, Episode 20, "The Blue Comet," poor Bobby was shot down in a public hit in a model railroad store. It was a sad end for a man who probably would have had a different career if he hadn't been born into this one.

The tragic tale of Adriana La Cerva (Drea de Matteo) was the saddest ending for any character on the show. The niece of Richie and Jackie Aprile, she was familiar with the temptations and perils of mob life and certainly didn't shy away from it. In dating Christopher Moltisanti and eventually becoming engaged to him, she clearly saw herself eventually living a life of luxury. Indeed, when Chris gave her a nightclub to manage, it was all that Adriana had wanted. 

Adriana had the misfortune of being targeted by the FBI as a potential way of getting incriminating information on Tony Soprano. They sent agent Deborah Ciccerone (Lola Glaudini) undercover to befriend her, and before long Adriana was blabbing her whole life's story to her. When Christopher hit on Deborah and Adriana blamed her, they brought Adriana in and told her that either she was going to jail or she was going to become an informant. Adriana reluctantly flipped but said as little as possible until a murder happened in her club that she tried to cover up. They wanted her to wear a wire and said she and Christopher could go into witness protection. When she told Christopher, he in turn told Tony, who made up a story about Chris being in an accident and had Silvio pick her up. Silvio took her to the woods and executed her. Chris chose Tony over her, or more precisely, he chose mob life. Adriana was killed in Season 5, Episode 12, "Long Term Parking."