Looking for some money he heard was stashed away by a friend of his beloved ma, Paulie ended up suffocating the friend with a pillow when she caught him rifling through her things.
Christopher Moltisanti was never much of a boyfriend, but he reached an all new level of depratvity when he sold his longtime girlfriend out to the family and Tony subsequently sicced the memorably coiffed Silvio Dante on Adriana.
Tony, Silvio and Paulie shoot their FBI informant pal to death while on a boating trip and dump him in the ocean—one of the hardest triggers Tony ever had to pull in six seasons.
We could see it building throughout season four, but when Tony's wife finally exploded with rage over his latest infidelity and admitted to falling for his driver, leading to their temporary separation...Chills. "I felt probably like someone who was terminally ill and somehow they managed to forget it for a minute!" Carmela spit at him.
Newly single (not that it ever stopped him with anyone else), Tony makes a play for his longtime shrink, who politely rejects her favorite sociopathic patient's advances.
Tony Blundetto tried to go legit but just ended up beating the crap out of his boss instead. After he agrees to do a job for a rival family, big Tony has to take his cousin in hand...with a shotgun blast to the face.
Tony had endless reasons to kill the relentlessly scummy Ralph Cifaretto, but it ended up being the death of the race horse Pie-O-My in a fire that Ralph set for insurance reasons that sent Tony into a murderous rage—and sent Ralphie's head packing.
Soprano family goon Vito Spatafore ditches his family and takes off to be openly gay in a small New Hampshire town. He finds love with a diner owner who he nicknames "Johnny Cakes," but eventually the pull of New Jersey takes him home. Things don't end well for him.
Even Tony's right-hand goon couldn't escape the vengeful blood-letting that dominated the series' last few episodes. Sil only ended up in a coma, though, so...maybe he and Tony made it out alive in the end that David Chase wanted us to always wonder about.
Was any moment of The Sopranos more shocking than the last second, when Journey's "Don't Stop Believin'" abruptly stopped and the entire series cut to black? Debate rages to this day over whether creator David Chase was being a genius or a jerk.
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