Ranking The Most Satisfying Character Deaths From ‘The Sopranos’

Every great show has a villain that we, as an audience, outright revile. We not only root for their demise, but we wonder how it will happen as opposed to when it will happen, and when it does, we expect it to make up for all those terrible things they’ve done over the course of the show. And when it does, we relish those moments. When talking about a show like The Sopranos (available to stream anytime on HBO Now), this is an entire cast of double-crossing, homicidal mobsters who lie, cheat, and steal for a living. While the show had its antihero in Tony Soprano (James Gandolfini), to be a villain on The Sopranos takes a special kind of character, one who’s repulsive even by the standards of other criminals. But when they went down, it was an occasion worth celebrating. So, for all those moments of collective bloodlust, here are five great Sopranos character exits that likely made you smile.

Mikey Palmice

While Tony’s uncle, Junior Soprano (Dominic Chianese), was the show’s big bad throughout the first season, it was Mikey Palmice who became the first character we actively rooted against. Even though he was fiercely loyal to Junior, he was strongly disliked by his friends, enemies, even his neighbor’s dog. However, as Junior rises to power (or so he thinks), Mikey was there to eagerly cling to his coattails and carry out his orders without a second thought.

Mikey was not only cocky and mean-spirited, he was just an all-around unpleasant guy, though it was the rancor between him and Tony that really cemented him as a loathsome character. Tony may have loved and respected his uncle Junior, but he didn’t have a shred of respect for Mikey, and he made no effort imply otherwise. Naturally, there’s a tremendous sense of payoff when he’s gunned down in the woods by Paulie (Tony Sirico) and Christopher (Michael Imperioli) on his morning jog — complete with him begging for his life out of sheer desperation. When it was over, he proved to be so despised that Christopher couldn’t stop shooting him, even after he ran out of bullets.

Richie Aprile

Released from jail with a real chip on his shoulder, Richie Aprile (David Proval) starts out by being welcomed back into the family with open arms. But once he starts making the rounds of his old neighborhood, that chip on his shoulder manifests itself when he beats up family associate Peter “Beansie” Gaeta (Paul Herman) in one of his own restaurants, all over the fact that he never came to visit Richie in jail. Despite Beansie’s best effort to try and stand his ground, Richie waits for him outside one night, running him over and crippling him in the process. And this was all over the course of a single episode.

The more he was around, the more Richie proved to be a constant thorn in Tony’s side, always feeling entitled to more than he was getting. All the while, Tony’s sister Janice (Aida Turturro), works to convince him to take action against her younger brother. While Richie’s gut reaction is to stay loyal to the family — arguably his only redeeming characteristic — before long he starts plotting Tony’s murder. Once Tony gets word of all this, he makes plans of his own, but neither end up panning out, as Richie ends up shot to death by Janice after hitting her during an argument. When Janice collapses into a panic afterward, she (of course) turns to Tony for help, and as he cautiously enters her kitchen, his smile when he sees Richie’s body on the floor mirrors our sentiments perfectly.

Ralph Cifaretto

Of all the despicable characters that The Sopranos paraded around over six seasons, none were more universally despised than Ralph Cifaretto (Joe Pantoliano). A wily, coke-addled mobster whose penchant for violence was shunned even by his fellow wiseguys. Tensions between Tony and Ralph were always high, but after Ralph brutally beat a girl to death outside The Bada Bing Club, Tony’s hatred of Ralph could no longer be contained. The two ended up coming to blows, which set off even more turmoil throughout the family.

Eventually, Ralph and Tony were able to squash their beef, and despite their truce, most fans were surprised to see Ralph make it out of the third season alive. It wasn’t until halfway through the fourth season, when an accident lands Ralph’s son in a coma, that we start to see a different side to him — a caring father. Beside himself with grief, Ralph starts to slowly unravel, breaking down in tears and even feeling remorse over things he’d done. It’s a testament to The Sopranos to have gone out of their way to make such a revolting character so surprisingly empathetic, even if those sentiments were short-lived.

After all, it’s in this very episode that Tony pays a fateful visit to Ralph’s house, and their discussion about scrambled eggs quickly turns into him accusing Ralph of killing their racehorse, which Ralph ends up admitting. A brutal fight breaks out and ends with Ralph laying dead on his kitchen floor. Once the moment’s initial shock wears off, we’re treated to 40 more minutes of nothing but Tony and Christopher (stoned on heroin) methodically disposing of Ralph’s body, giving us plenty of time for the reality of his death to sink in and for us to smile over the realization that we’d never have to hear another bad Gladiator quote again.

Phil Leotardo

Introduced early in the show’s fifth season along with a group of recently-released criminals, Phil (Frank Vincent), started off as little more than a minor inconvenience to Tony. Still, he was a merciless killer who helped Johnny Sack (Vincent Curatola) win his war with “Little” Carmine Lupertazzi (Ray Abruzzo) over control of the New York family. We didn’t start to see what Phil was truly capable of until his brother, Billy (Chris Caldovino), was killed in a botched assassination attempt by Tony’s cousin, Tony Blundetto (Steve Buscemi).

From that moment on, Phil had a straight-up vendetta against the Soprano family, particularly after Tony takes it upon himself to solve their problem with his cousin, robbing Phil of the satisfaction he’d planned on getting. Not long after, once Johnny Sack is out of the picture and in federal holding, Phil goes on a mission to make life for Tony Soprano as miserable as possible before electing to end it. During the final episode, Tony learns from his longtime frenemy Agent Harris (Matt Servitto) where Phil had been hiding out, and once Tony’s crew tracks him down, his sudden, and decidedly non-cinematic death, is every bit as shocking as it was satisfying.

Christopher Moltisanti

This may surprise you, but if you look within yourself, you’ll admit that you were kind of happy to see Christopher’s story end. For years, Christopher was being groomed to be Tony’s replacement despite being on perpetually thin ice for his behavior. He was both a failed dreamer and an irrational hothead who regularly relapsed into drug and alcohol addiction, constantly putting Tony’s entire operation in jeopardy. Still, for all his screw-ups, Tony was always there to give him another chance. Maybe it was the fact that Tony himself was so dependent on his therapy that no matter how many times Christopher came close to the brink, he was always there to forgive him.

As the end of the show drew near, the relationship between Tony and Christopher soured. Christopher became increasingly distracted from his life in the mafia, coupled with a self-imposed isolation brought about by another attempt at sobriety, all of which turned into a deep-seated resentment for his former mentor. He relapsed one last time, never able to firmly grasp sobriety, and his carelessness cost him his life on a dark country road. As he sat in his car bleeding to death, Christopher’s life was finally snuffed out by Tony while he rambled on about the drugs in his system.

While everyone in his world mourned the loss of Christopher, Tony only spoke of relief and took a trip out to Las Vegas, where he did enough celebrating for everyone.