The Most Brutal Deaths In The Sopranos

While "The Sopranos" had a critically-beloved run that resulted in 21 Emmys, "College" (Season 1, Episode 5) might be the most highly-regarded episode, right up there with "Pine Barrens" and "Whoever Did This."

The defining encapsulation of Tony Soprano's balancing act as half gangster, half family man, the episode employed this stark contrast to depict a man attempting to violently multi-task, but with both worlds constantly threatening to fall apart. Okay, maybe Tony was more like 3/4 gangster, 1/4 family man. 

The episode began with Tony and his daughter Meadow touring universities in Maine, some 500 miles away from New Jersey. During a stop at a gas station, Tony noticed a familiar figure cleaning his car. When Christopher Moltisanti ran the plates, Tony knew it was Fabian Petrulio, a former "made guy" who was put into the witness protection program after becoming a valuable informant. 

Of course, Fabian spotted Tony, too — and the result was a sharp detour from college recruitment. After 24 hours of following each other, Tony proved himself to be a 250-lb ninja, pouncing on Fabian with a Garrotte wire, strangling him to death. It would be the first of Tony Soprano's eight murders on the show.

Season 3, Episode 5 opened with Mustang Sally, a despicable scumbag, attacking Bryan Spatafore with a golf club, causing massive damage to his skull and leaving him for dead on the sidewalk. Performed by the late Brian Tarantina, Sally did this during a public argument with his girlfriend, who had the nerve to ask Bryan for a lift uptown.

Unfortunately for Sally, Bryan was the brother of Vito, one of Tony's men. Soon enough, Mustang Sally had a target on his head, and Tony wanted Bobby Baccalieri Sr. to do the hit, even though he was suffering from advanced lung cancer. Actor Burt Young must have given himself a raw throat, as most of his work here is conveyed through a series of coughing and spluttering. It was a wheezing, eye-watering, gory cough that was hard to watch.

Although concerns were voiced about Bobby's suitability for this hit (especially from his son Bobby Jr.), Bobby Sr. possessed a serious case of bloodlust. Mustang Sally being his godson seemed to only add to the excitement of the hit, which unfolded with a blown-off ear and brain matter on the ceiling. 

Once he was done, a blood spattered Bobby Sr. drove away smoking a pack of Camels, sending his shredded throat into such a frenzy that he crashed into a signpost and died on impact. An utter debacle, all around.

Tony never liked Ralph Cifaretto, even before he killed Tracee or refused a conciliatory drink. The only thing that kept Ralph breathing was his ability to crack heads and earn money. 

That changed, however, with the death of Ralph's racehorse Pie-O-My, for whom Tony had genuine affection. Although the old girl got some big wins at the track, she was blighted with colic and other expensive maladies, costing Ralph thousands in medical bills. Ralph also had to share his winnings with Tony because in the mob world, everything flows up. 

So, when Pie-O-My died in a stable fire, Tony became suspicious. The fire department declared it an accident, but Tony knew Ralph had access to skilled arsonists such as Corky Ianucci — hired to immolate Artie Bucco's restaurant in Season 1. After viewing Pie-O-My's charred remains, he drove to Ralphie's house to break the bad news. Sincere condolences were then followed by snide remarks, which were followed by physical violence involving a colander, a carving knife, and a can of bug spray. 

In this violent tussle, Tony overpowered Ralph and began battering his head into the stone tiled floor, shouting: "She was a beautiful, innocent creature, what did she ever do to you?!" Whether he was referring to Pie-O-My, Tracee or perhaps both was unclear. 

Chris and Paulie had one of the most amusingly contentious relationship on the show, always bickering and often times coming to blows. This acrimony was central to "Pine Barrens," a self-contained story of the hapless pair lost in the New Jersey Pine Barrens. 

Their relationship's most brutal occasion occurred outside a restaurant, after Chris had been forced to foot a $1200 tab that Paulie increased with frivolous purchases. Just as the pair began to square off, a waiter approached them with complaints over his small tip. Much like Michael Imperioli's previous character Spider in "Goodfellas," the waiter made the fatal error of insulting two egotistical mobsters. 

Naturally, Chris responded by throwing a brick at his head, sending him into a violent seizure. Realizing that he was in a very bad way, Paulie finished the waiter off with a round to his chest, then made off with the money they had just paid.

Tony hated Ralph, but he loved Tony Blundetto. Or rather, he had an affection for him that was twisted with guilt because of a truck heist that sent Blundetto to the can for 17 years. 

Soprano was supposed to have been in Blundetto's place on that heist, but he was incapacitated by a bad panic attack. So, when Blundetto returned to his old stomping ground, Soprano wanted to accommodate him as best he could. After all, Blundetto had balls — and a 158 IQ — a rare combination. 

However, Blundetto became a free agent, whacking several people including Billy Leotardo — the brother of Phil Leotardo, the most vindictive man in the series. Not unreasonably, Billy's death sent Phil into violent frenzy, as he demanded to know where the "animal" Blundetto was and made threats against the whole Soprano crew, which Tony knew were very legit. Tony also knew that if Phil found Blundetto, his death would be agonizing. 

So, in an act of mercy, Tony lied in waiting at Blundetto's hideout. When Blundetto returned from grocery shopping, Tony blasted him in the head with a pump action shotgun, sending his body into a pile of logs. 

This was the moment that redefined Phil Leotardo as the worst kind of evil, reptilian scumbag. Already a nasty piece of work, his scheming brutality here was just hateful. 

After Vito was spotted performing a sex act on a man and then found in a gay club, he fled Jersey and went on the run, picking up odd jobs in rural New England. However, the reality of actually having to work proved to be too much, so Vito returned to Jersey claiming that his homosexuality was caused by medication and that he's all "better" now.  

Paulie wanted blood, but Tony was split. If he could, he'd make room for Vito somewhere, perhaps in a job "running girls" in Atlantic City. After all, he's a good earner. 

Unfortunately, in their malignant world, Vito's safety was impossible. So Leotardo and his men — including Fat Dom — waited for Vito in his motel room, where they ambushed him with duct tape and batons, beating him to death.

Unlike his father — the executioner in the Mustang Sally debacle — Bobby Baccala was a "gentle giant" type. Soft, fat and cuddly. Unless, of course, you incessantly joke about his wife Janice, Tony's malignantly awful sister. 

This scene kicked off during Tony's birthday weekend at Bobby and Janice's cabin in upstate New York. The drinks were flowing so liberally that you could almost smell the liquor, and the vibes were good and the surroundings beautiful enough that you never could have seen what was coming — even on a show like "The Sopranos." 

Ultimately, nothing could pacify the toxic relationship between Janice and Tony — who made a series of snide remarks about her promiscuity. An inebriated Bobby took exception, but Tony didn't take him seriously. As he made another salacious joke, Bobby punched him in the face. Tony, no doubt shocked by Bobby's newfound "balls," tore into his brother-in-law as best he could, but Bobby won the fight. 

Tony, of course, blamed things of his gunshot injury and the rug, but he seemed fine with his butt-whooping. In actuality, he was formulating a nasty plan to get his vengeance another way. 

Bobby had never killed a man, so Tony made that happen for him, organizing a hit on a Montreal hoodlum. The hit could be passed off as just part of Bobby's job, but Tony purposefully did this to make Bobby uncomfortable. Bobby passed the challenge, but it became a personal, bloody act. 

This may have been the most cathartic moment of "The Sopranos." David Chase and his writers knew that they couldn't just whack Phil Leotardo. They had to get creative, and they did so brilliantly. 

Yet, Phil's death was not some overly-elaborate set piece, but instead a wonderfully chaotic, gory end to a genuine demon of a man. This was Season 6, Episode 21 — the final episode of what many still consider the finest show in TV history. 

Phil's Lupertazzi crime family had killed Bobby Bacala and seriously injured Silvio Dante in their attempt to kill the Soprano leadership and "do business with what's left." Tony and his family went into hiding as he tried to locate Phil, who had also "hit the mattresses." Just as the odds seemed stacked against Tony, he managed to sanction the hit on Phil, which was enabled by vital information from Special Agent Harris, Tony's old FBI foe who had been jaded by the War on Terror. 

The scene was modestly staged. Phil and his wife Patty were on a trip with their young grandchildren when they stopped at a gas station. Just before he went to make a phone call, Phil reminded Patty of some menial task that needed doing — and a gun appeared next to his head, firing a round into the base of his skull. Patty screamed as the hitman fired another round into his chest, making off in a getaway vehicle. 

In many ways, it was a standard hit. But then Patty put the automatic gearbox in drive as she exited the car in hysterics, inching the car forwards toward Phil's head and accidentally crushing it with the car's rear wheel. In the mob business, the end result was what they would label a "beautiful hit."