The Sopranos: 20 greatest moments from HBO’s classic drama series

The Sopranos: 20 greatest moments from HBO’s classic drama series

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.

The 20 best moments from The Sopranos

The 20 best moments from The Sopranos - 20-1: (HBO)
The 20 best moments from The Sopranos - 20-1: (HBO)
20. Nancy Sinatra’s cameo: <b>Season six – part one, episode four</b>:
20. Nancy Sinatra’s cameo: Season six – part one, episode four:

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. (HBO)" />

19. Junior's C-words: <b>Season two, episode two</b>:
19. Junior's C-words: Season two, episode two:

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***.” (HBO)" />

18. The moll life juxtaposition: <b>Season six – part one, episode 11</b>:
18. The moll life juxtaposition: Season six – part one, episode 11:

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**.” (HBO)" />

17. Tony’s terrifying dream: <b>Season four, episode 11</b>:
17. Tony’s terrifying dream: Season four, episode 11:

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. (HBO)" />

16. Tony tells Carmela about Bobby: <b>Season six – part two, episode eight</b>:
16. Tony tells Carmela about Bobby: Season six – part two, episode eight:

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. (HBO)" />

15. Pussy is whacked:
15. Pussy is whacked:
14. Ralph runs out of chances: <b>Season four, episode nine</b>:
14. Ralph runs out of chances: Season four, episode nine:

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. (HBO)" />

13. Furio and Carmela: <b>Season four, episode four</b>:
13. Furio and Carmela: Season four, episode four:

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. (HBO)" />

7. Tony mixes the personal with the professional: <b>Season one, episode five</b>:
7. Tony mixes the personal with the professional: Season one, episode five:

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. (HBO)" />

12. Christopher’s nightmare: <b>Season one, episode eight</b>:
12. Christopher’s nightmare: Season one, episode eight:

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. (HBO)" />

Prequel film, The Many Saints of Newark, was released in 2021.