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Those sitting down to watch The Sopranos in 1999 had no idea David Chase’s US gangster series would become a cultural touchstone that enabled other showrunners to get future acclaimed shows off the ground.
On the surface, the series was another Mafia thriller in a similar vein to Scorsese’s Goodfellas . But beyond the violence and machismo was a complex and brilliantly unpredictable drama about a dysfunctional family, with James Gandolfini’s flawed, anxiety-ridden Tony Soprano at its helm.
Helped by its standout cast (Gandolfini, Edie Falco, Michael Imperioli, Dominic Chianese, to name but a few), The Sopranos remains as watchable and enjoyable as it’s ever been.
We’ve compiled the 20 best moments from its 86 episodes, which you can see in the gallery below.
A book, titled The Sopranos Sessions , was released in time for the show’s 20th anniversary in 2019. Within its pages is what appears to be Chase’s confirmation of what actually happened to Tony in the show’s controversial final scene.
Show all 21 1 /21The 20 best moments from The Sopranos The 20 best moments from The Sopranos The 20 best moments from The Sopranos - 20-1
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The 20 best moments from The Sopranos 20. Nancy Sinatra’s cameo Season six – part one, episode four : "Chasing It"
The Sopranos featured several surprising guest stars – Lauren Bacall, Sir Ben Kingsley, Annette Bening – but none were bigger for New Jersey than Nancy Sinatra, who plays herself and sings “Bossman” at the “making” ceremony for Phil Leotardo (Frank Vincent).
Her younger brother Frank Sinatra Jr had appeared in season two episode “The Happy Wanderer” and their presence played as a joke about their father’s much-touted mob connections.
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The 20 best moments from The Sopranos 19. Junior's C-words Season two, episode two : "Do Not Resuscitate"
Dominic Chianese ensured Junior remained one of The Sopranos ‘s funniest and most terrifying characters throughout its six seasons. It’s his sporadic deployment of the C-word that looms large – most notably the season two scene in which he slips in the shower (”Your sister’s c***!”).
Another standout sees Junior berate his Russian nurse for not bringing Tony a coffee. “I’m registered nurse, not maid,” she tells him, to which Junior replies; “Well, did you offer him an aspirin? C***.”
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The 20 best moments from The Sopranos 18. The moll life juxtaposition Season six – part one, episode 11 : "Cold Stones"
This episode sees Carmela (Edie Falco) visit Paris with Rosalie Aprile (Sharon Angela). The mob wife is deeply moved by the beauty of the French capital: its atmosphere, its historic architecture and the view across the Seine.
Then, in one of the great comic cuts, director Tim Van Patten relocates to the parking lot of the Bada-Bing!, where Silvio (Steven Van Zandt) is overseeing the cleaning of the strip club’s famous neon girly sign: “Make sure you scrub that s*** off her t**.”
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The 20 best moments from The Sopranos 17. Tony’s terrifying dream Season four, episode 11 : "Calling All Cars"
The Sopranos ‘s dream sequences felt as if they were directly lifted from a David Lynch film. None came more terrifying than the one at the climax of this season four episode, which sees Tony (James Gandolfini) lured to an old house by Ralph Cifaretto (Joe Pantoliano), whom he’d murdered two episodes before.
Looking through the door of the seemingly abandoned building, he sees a shadowy figure walking down the stairs. It looks on in silence, bearing a face that resembles his deceased mother’s. It's star, unexplained and sets hairs on end every time.
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The 20 best moments from The Sopranos 16. Tony tells Carmela about Bobby Season six – part two, episode eight : "The Blue Comet"
The murder of Bobby Baccalieri (Steve Schrippa) – Uncle Junior’s sweet-natured carer – is one of the show’s saddest, with the heavy gunned down in a toy shop while eyeing a Blue Comet trainset to complete his model railway. When Tony tells Carmela about the slaying, which means the family will have to go into hiding from Leotardo’s crew, she reacts hysterically, in disbelief that the day she most feared and refused to acknowledge has finally come.
The brilliance of the scene lies in the comparatively cool response of the far more pragmatic Rosalie, who quietly excuses herself, accepting the news as a reality of mob life.
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The 20 best moments from The Sopranos 15. Pussy is whacked Season two, episode 13 : "Funhouse"
The death of Sal “Big Pussy” Bonpensiero (Vincent Pastore) aboard Tony’s yacht after the boys confront him about being an FBI informant is as bitter as it is ugly, bringing season two to a bleak climax. Sal’s increasingly frantic attempts to justify his actions in the gently rocking darkness of the boat’s cabin is desperate stuff.
The disgust on the face of Tony, already sick with food poisoning, as the group raise a parting glass spells doom in one of the series’s most intense and complex moments. “You were like a brother to me,” Tony spits, before weighing down the Fat Man’s body and tossing him into the sea. Gulls caw overhead.
The 20 best moments from The Sopranos 14. Ralph runs out of chances Season four, episode nine : "Whoever Did This"
Joe Pantoliano made a huge impression as Ralph Cifaretto, one of the show’s most vile and brutal recurring characters (see number 11). Tony finally does the decent thing in season four, throttling the self-confessed “sick f***” to death on his own kitchen floor, believing him to have razed the stables in which his beloved racehorse Pie-O-My was burnt to death for the insurance money. Such periodic eruptions of violence remind us just how ruthless Tony Soprano truly is.
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The 20 best moments from The Sopranos 13. Furio and Carmela Season four, episode four : "The Weight"
It’s a wonder Furio Giunta (Federico Castellucio) makes it out of the series alive. After being employed by Tony, Furio moves to New Jersey and eventually falls for Carmela (Edie Falco) who views the long-haired Italian as a polar opposite to her husband. While never consummating their feelings, one scene perfectly encapsulates the effect he’s had on Carmela: while having sex with Tony, all she can think of is the music she sensually danced with Furio to the previous night.
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The 20 best moments from The Sopranos 7. Tony mixes the personal with the professional Season one, episode five : "College"
In one of the show’s earliest acclaimed episodes, Tony drives Meadow (Jamie-Lynn Sigler) to Maine for a tour of prospective campuses ahead of her high school graduation. His daughter takes the opportunity to grill him on the family business, exposing Tony’s hypocrisy and the layers of deceit the Soprano clan must live under.
At a petrol station, Tony spots Fabian Petrulio (Tony Ray Rossi), a former DiMeo consigliere turned rat now living under the Witness Protection Programme. He duly garrottes him while Meadow is in an interview, bringing his two worlds uncomfortably close together.
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The 20 best moments from The Sopranos 12. Christopher’s nightmare Season one, episode eight : "The Legend of Tennessee Moltisanti"
Christopher Moltisanti (Michael Imperioli) suffers a haunting in the first of the show’s brilliantly Lynchian sequences, in which he is tormented by the memory of the first person he ever killed, Czech gangster Emil Kolar (Bruce Smolanoff). Taking place in Satriale’s Pork Store, Christopher imagines the dead man returning from the grave to place an order for sausages, corpses reaching out from within the meat freezers as “You” by The Aquatones plays in the background. Chilling.
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The 20 best moments from The Sopranos 11. Tony shows humanity after Ralph’s brutal act Season three, episode six : "University"
When Ralph brutally kills Tracee (Ariel Kiley) – a pregnant stripper he’s been dating – in the parking lot of the Bing, Tony steps in. It’s a rare moment in which the protagonist displays a tender side you yearn for him to showcase more often. The likeable Tracee’s death is one of the hardest to watch among all The Soprano ’s grisly ends.
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The 20 best moments from The Sopranos 10. The intervention Season four, episode 10 : "The Strong, Silent Type"
It was a delight whenever the series brought most of the ensemble together, and no scene worked much better than the intervention of a drug-addled Christopher. It was the payoff – in equal parts painful and hilairous – of four seasons’s worth of simmering tensions that chillingly foreshadowed James Gandolfini’s untimely death in 2013.
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The 20 best moments from The Sopranos 9. Janice proves she’s a true Soprano Season two, episode 12 : "The Knight in White Satin Amour"
It’s a feral punch to the face, courtesy of fiancée Richie Aprile (David Proval), that causes the Soprano blood of Tony's sister Janice (Aida Turturro) to truly begin flowing. Her response is to shoot him in the chest twice, taking out what was one of the show’s more ruthless creations whose body's destroyed by Satriale's meat-cutter mere scenes later.
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The 20 best moments from The Sopranos 8. The fatal nose-pinch Season six – part two, episode six : "Kennedy and Heidi"
Nobody placed a burden on Tony more than Christopher, and the notion that their blood relation would keep him alive came crashing down around viewers ten minutes into one of the show’s final episodes. After a drunken Chris crashes his car, Tony – instead of helping him – pinches his nostrils shut and watches his nephew choke to death on his own blood. It’s a shocking scene, layered with visual subtext explaining Tony’s unspoken thoughts (he sees a branch has impaled the baby seat where Chris’s daughter could have been sitting).
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The 20 best moments from The Sopranos 6. AJ tries to kill himself Season six – part two, episode seven : "The Second Coming"
Tony and Carmela’s son (Robert Iler) endures a miserable adolescence, believing he’s unfit for the world he’s been born into and unable to express himself. AJ attempts to end his own life by tying a cinder block to his ankle and plunging into the family swimming pool – once home to the ducks his father found such significance in – only to regret it at the last minute, forcing Tony to dive in and save him. “What’s wrong with you?!” his father screams as the boy recovers his breath, a roar of incomprehension that contains a genuine question.
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The 20 best moments from The Sopranos 5. The final scene Season six – part two, episode nine : "Made in America"
The debate over whether certain final scenes of television shows are actually good will rage on and on. The Sopranos remains front and centre of the conversation. It's a seemingly banal occasion – a restaurant dinner scene. We watch on as Tony sits there, observing other customers. Carmela arrives, then AJ and Meadow, who the last we see, is parking her car outside. A bell rings, Tony looks up and the screen cuts to black. It’s an ending that’s inspired essays offering varied interpretations but ultimately, it remains a beautifully-executed few minutes of television.
The 20 best moments from The Sopranos 4. Melfi almost tells Tony Season three, episode four : "Employee of the Month"
“You wanna say something?” Tony asks his visibly distressed psychiatrist Doctor Jennifer Melfi (Lorraine Bracco) after she discovers her rapist has been let free due to a police error. She knows – we know – a response in the affirmative will spur Tony's killing instinct into action, but to do so would be to shun her ethics. It’s impossible to watch this moment and not yearn for Melfi to answer differently. But she doesn’t. Melfi’s simple delivery of the word “no” is one of the most haunting moments of the entire series.
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The 20 best moments from The Sopranos 3. Adriana is whacked Season five, episode 12 : "Long Term Parking"
Christopher’s long-suffering girlfriend, Adriana (Drea de Matteo), is cornered by the FBI at Crazy Horse, the nightclub she manages, and forced to turn informant or face prison for allowing cocaine distribution to go ahead inside, unchallenged. Living in terror, she confesses the truth to Christopher who almost chokes her before leaving in tears. Out of loyalty to Tony, he gives Adriana up. Silvio, seemingly the man most likely to show mercy, drives her out to the woods and shoots her in the back of the head. A tragic end for one of the show’s sparkiest personalities.
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The 20 best moments from The Sopranos 2. Tony and Carmela’s showdown Season four, episode 13 : "Whitecaps"
For a show filled with merciless murder, it’s telling that the most uncomfortable moment to sit through is one that depicts the dissolution of a marriage. But it’s also evidence as to why The Sopranos has endured as one of the greatest dramas all the time: beneath its gangster genre veneer was something altogether more affecting and personal. Re-watch Tony and Carmela’s showdown, sparked when the former’s infidelity finally creeps into their family home, and you’ll be convinced there’s been no better acted moment in television history. There probably hasn't been.
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The 20 best moments from The Sopranos 1. Pine Barrens Season three, episode 11 : "Pine Barrens"
Often considered the show’s finest achievement, this Chekovian season three episode directed by Steve Buscemi sends Christopher and Paulie (Tony Sirico) into the forest after botching the execution of Russian gangster, Valery (Vitali Baganov). Some glorious black comedy ensues as they pursue the wounded man and get deeply lost in the snow.
The execution of Professor Quadri in Bernardo Bertolucci’s Italian gangster film The Conformist (1970) is often cited as an inspiration, as it was for Francis Ford Coppola in shooting The Godfather (1972).
Buscemi would act in the show himself from 2004 as Tony Blundetto in season five, securing an Emmy nomination for his work as Tony Soprano’s cousin, newly released from prison and determined to go straight before being drawn back into the family business.
"Pine Barrens" remains a television masterclass.
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Prequel film, The Many Saints of Newark
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