We are a little over a month away from the 20th anniversary of one of the greatest TV shows ever made: The Sopranos, which may be the most-copied series since I Love Lucy. Peak TV would not exist without Tony, Carmela, Paulie Walnuts and friends.
In the course of writing The Sopranos Sessions, our book about the series (with essays on every episode and a new series of interviews with creator David Chase), my co-author Matt Zoller Seitz and I had an excuse to rewatch the entire series, and to be reminded of just how bloody brilliant so much of it was. Works of art this famous and this influential can suffer when revisited years later in an environment that they helped create. The Sopranos, though, held up phenomenally well — not just in the performances of James Gandolfini and Edie Falco, but in the deep reservoir of emotion Chase and company were able to tap into despite many of their characters being reprehensible sociopaths.
(Note: Though the show officially has only six seasons, that last batch of 21 episodes was really two separately-produced seasons labeled one to avoid giving too many of the cast and crew their guild-mandated raises. Chase considers the nine episodes that aired in the spring of 2007 to be the seventh Sopranos season, and so do we.)
10. “The Second Coming” (Season 7, Episode 7)
The controversy over the series’ concluding scene tends to obscure memory of just how tremendous that final batch of episodes was. Chase and company do a masterful job of stripping the life of Tony (Gandolfini) down for parts, severing many of his closest relationships and displaying his destructive narcissism like never before. As the poem that gives this episode its title says, things fall apart; the center cannot hold. And as the boss’s work seems to be nearing catastrophe via the war with Phil Leotardo (Frank Vincent), he barely prevents a tragedy in his personal life, diving into the family pool to rescue a depressed A.J. (Robert Iler) from a suicide attempt. All the misery and angst Tony has visited upon the world now comes back at him with unrelenting force.
9. “Join the Club” (Season 6, Episode 2)
The series had done extended — and polarizing — dream sequences before. What happens in the wake of Tony being shot by Uncle Junior (Dominic Chianese) in the previous episode feels different, and haunting. “Join the Club” toggles between tragic earthbound concerns as Carmela (Falco, who’s particularly gut-wrenching here) prepares herself for the idea that her husband might die, and a more cosmic alternate reality where Tony is a salesman who begins to lose both his physical and mental identity the longer he’s trapped there. It’s the show’s two stylistic extremes in one incredible package.
8. “Whoever Did This” (Season 4, Episode 9)
From the moment when the show introduced Joe Pantoliano’s obnoxious Ralphie Ciffaretto in Season Three, fans seemed to be counting the days until Tony had him whacked, particularly after the caporegime murdered a stripper in the Bing parking lot in that season’s “University.” Instead, the show delayed our bloodthirsty gratification for more than a year with this shocking, oblique-angled entry, where it’s the arson-related death of Tony’s beloved horse Pie-O-My that finally gets Ralphie’s skull bashed in, then chopped off. The graphic, extended corpse-disposal sequence is among the more influential things the show ever did, even as the timing and manner of Ralphie’s murder is uniquely Sopranos.
7. “Amour Fou” (Season 3, Episode 12)
Nancy Marchand died before production of this season began, robbing the series of Tony’s greatest nemesis. But his mother’s spirit very much hung over this year with the introduction of the electric Annabella Sciorra as Gloria Trillo, a sexy saleswoman who would prove far darker and more self-destructive than Tony imagined when they met in Dr. Melfi’s waiting room. This hour brings their toxic relationship to a close (while also putting Jackie Aprile Jr’s life in jeopardy after he’d mostly been comic relief), as a suicidal Gloria offers Tony a chance to finish the job he couldn’t with Livia at the end of Season One.
6. “The Knight in White Satin Armor” (Season 2, Episode 12)
Even more startling than Ralphie’s demise was the way the series got rid of his predecessor as the professional thorn in Tony’s side. Much of Season Two suggests that Tony and David Proval’s Richie Aprile will go to war. Instead, Tony’s impulsive sister Janice (Aida Turturro) guns down Richie after he punches her in the face, inadvertently saving her brother and providing the series with one of its most iconic moments. Almost as memorable: the last real interaction between Tony and Livia, which ends with her once again laughing at his suffering.
5. “Pine Barrens” (Season 3, Episode 11)
This black comic masterpiece, where Christopher (Michael Imperioli) and Paulie (Tony Sirico) get stranded in the eponymous Jersey landmark after an attempt to collect a debt from a Russian gangster goes terribly awry, is something of a gateway drug for the entire series. The gangster-out-of-water elements were so surprising at the time and have been so imitated in the ensuing years that the episode’s other plotline — about things starting to sour between Tony and Gloria — has arguably aged better. But the increasing desperation and stupidity of these two goons in the wilderness is never not funny, and the snowstorm that hit the Garden State right before filming began gives director (and future castmember) Steve Buscemi the operation to create some of the series’ most striking visuals.
4. “Whitecaps” (Season 4, Episode 13)
The show’s longest episode is also its best acting showcase for Gandolfini and Falco. After a frustrating (for her and the viewer) season-long flirtation with Furio goes nowhere, Carmela is primed to explode upon learning of Tony’s latest infidelity, and she finally works up the nerve to order him out of the house. The problem is that she only has so much power over this monster she chose to marry, and the two continue emotionally tearing each other apart after he moves into the pool house. Theatrical, raw, brilliant.
3. “I Dream of Jeannie Cusamano” (Season 1, Episode 13)
In terms of the Family vs. family conflicts that drove all the early marketing, the series peaked with its first season. No future opponents could possibly bring the two halves of Tony’s life together better or more painfully than his mother and his uncle. The endgame of that arc plays out spectacularly: Tony explodes when Dr. Melfi (Lorraine Bracco) tries to make him see the danger that his mom poses to him. He then marches into the retirement community with a pillow in his hand, and Livia is saved only by a conveniently-timed stroke that Tony (rightfully) believes she’s faked.
2. “Long-Term Parking” (Season 5, Episode 12)
The Sopranos didn’t win its first Emmy for Outstanding Drama Series until the end of its fifth season. This heartbreaking episode — the climax to a multi-season arc about Christopher’s girlfriend Adriana (Drea de Matteo) being turned into an FBI cooperator against her will — is almost singlehandedly responsible for that win. The series was never as interested in being a straightforward Mob drama as some of its fans desperately wanted it to be, but episodes like this one showed how perfectly it could shift into that made when the story demanded it.
1. “College” (Season 1, Episode 4)
This was the episode that made The Sopranos into the phenomenon it became, and the purest distillation of the show’s Family/family themes and the ways that Tony’s work in the former utterly taints the latter. On a tour of New England colleges with Meadow (Jamie-Lynn Sigler), Tony gets a chance to take vengeance on a Mob informant hiding out in the middle of nowhere. Back at home, Carmela and her trusted priest Father Phil (Paul Schulze) experience a night of mutual temptation, inspired by her mistrust of a philandering criminal husband. Tony acts on his impulses; Carmela doesn’t. But they’re both damned through his actions and her decision to stay with him. HBO was reluctant to show Tony murdering a man in cold blood, but Chase argued that the show would ring hollow if he didn’t. He was right, and the episode — and the series — turned out to be a masterpiece.
[Editor’s note: a version of this list was originally published in November 2018]