From 1999 to 2007,The Sopranosspanned six seasons and eighty-six episodes, forever altering the fabric of television.

As he conducts nightly bedtime rituals, Hesh talks to an off-screen Renata, who is already in bed.

When he realizes she isn’t responding, Hesh walks into the bedroom to find her lifeless body.

Custom image of the saddest deaths on The Sopranos

Image by Federico Napoli

Renata’s death is believed to have been a stroke, but never underestimate Tony’s reach.

Desperate to execute this plan,Eugene approaches Tony with giftsand a cut of his inheritance.

Dejected, Eugene returns home to an unimpressed wife and a teenage son with a drug addiction.

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Audiences watch in horror asEugene chooses his exit strategy.

Humiliating Phil and his family in this manner is punishable by death.

Vito briefly gets to live freely but is overcome with boredom and flees New Hampshire.

Jerry Adler as Herman “Hesh” Rabkin squints into the sun from the series The Sopranos

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In a scene reminiscent of Jackie Jr.’s final moments,Vito kills the man execution style.

While audiences weren’t invested in the Jeep Guy, his death was tragic and unnecessary.

The same can be said for Vito’s death in the next episode, “Cold Stones.”

New Jersey mobster Eugene Pontecorvo (Robert Funaro) talks to someone in the Sopranos

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Live free or die, indeed.

The waiter’s head injury results in a seizure, and a panicked Paulie shoots him.

RIP, bold food industry employee.

Joseph R. Gannascoli standing next to his car on the roadside in The Sopranos

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Tony’s tumultuous yet passionate fling with the Mercedes Sales Associate was memorablebecause of Sciorra’s fearless portrayal.

She didn’t put Carmela in that E-Series Wagon, but damnit, she tried.

Tracee forgets her place and implements a public tone Ralphie cannot abide.

Tony Sirico as Paulie Gualtieri and Michael Imperioli as Christopher look off-screen at a waiter who has met them outside of restaurant to talk about his tip in The Sopranos

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Ina gross exaggeration of punishment, the young woman’s time runs out before her twenty-first birthday.

In a show where random acts of violence are commonplace, the brutality that befalls young Tracee shocked viewers.

After bouts of debilitating ulcerative colitis brought on by extreme stress and anxiety,the belovedSopranoscharacter finally confidesin Christopher.

Annabella Sciorra as Gloria Trillo looks at Tony in backseat of car from The-Sopranos

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The ducks were great, but Pie-O-My was a splendid specimen capable of generating repeated revenue.

Next:The 10 Best Carmela Episodes on ‘The Sopranos,’ Ranked

Steven R. Schirripa as Bobby Bacala shops for toy trains from the episode The Blue Comet in The Sopranos

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Drea Matteo as Adriana with her dog Cosette look ahead during a car ride from The Sopranos

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Ariel Kiley looking at Joe Pantoliano with anger in The Sopranos

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Silvio driving a terrified Adriana in The Sopranos

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James Gandolfini as Tony Soprano sits in a barn with his dead horse Pie O My and a goat

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