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The Sopranos 25th anniversary: the 10 best episodes, ranked

As the acclaimed mob drama marks its 25th anniversary, Louis Chilton selects 10 of the finest episodes from this TV masterwork

Wednesday 10 January 2024 08:03 GMT
Tony (James Gandolfini) and Carmela (Edie Falco) air their grievances in the coruscating ‘Whitecaps'
Tony (James Gandolfini) and Carmela (Edie Falco) air their grievances in the coruscating ‘Whitecaps' (HBO)

Just when I thought I was out, they pull me back in… to a rewatch of The Sopranos, that is. Today, the inimitable mafia series – often hailed as the greatest TV drama of all time – celebrates its 25th anniversary, with Warner Bros sharing a glut of new behind-the-scenes content.

The series, which starred James Gandolfini as brutal but charismatic mafia boss Tony Soprano, and Edie Falco as his wife Carmela, helped redraw the boundaries of narrative television. Though Gandolfini tragically died in 2013 at the age of just 51, his performance remains one of the best and most widely acclaimed screen performances ever. And the show continues to win over new and younger audiences, while its myriad imitators have faded away.

Created by David Chase, The Sopranos was a masterclass in episodic storytelling, weaving standalone stories into longer serialised plotlines with effortless grace. Many of the best episodes are intimately familiar to many of the show’s fans: the words “Pine Barrens”, for example, demand no elaboration.

And then, of course, there was the finale. After six seasons on the air (including a bifurcated double-length final season), The Sopranos finally came to a halt in 2007, with the violently polarising “Made in America”. To the end, this was a show that innovated, and deconstructed and refused to pander. To this day, there’s not been anything quite like it.

Here’s a rundown of the 10 best Sopranos episodes, ranked…

10. Season two, episode 13: “Funhouse”

Perhaps the most divisive aspect of the series – other than its infamous “cut to black” ending – is the several episodes devoted to indulgent, surrealist dream sequences. The most memorable and effective of these is the season two finale “Funhouse”, in which a bout of nasty food poisoning (possibly caused by “that f***ing Artie Bucco”) prompts Tony to have a series of revelatory dreams about lifelong friend turned FBI snitch “Big Pussy” Bonpensiero. It wasn’t just Pussy that ended up sleeping with the fishes – but the very rudiments of TV storytelling convention.

9. Season four, episode 10: “The Strong, Silent Type”

For an episode that veers into some pretty distressing subject matter – domestic abuse; addiction; a violent carjacking – “The Strong, Silent Type” is oddly one of the funniest Sopranos episodes, containing two of the series’ most inspired comic sequences. The first sees the tight-fisted Paulie (Tony Sirico) secretly take in the portrait Tony had commissioned of himself and prized racehorse Pie-O-My, having the painting altered to depict the New Jersey crimelord in Napoleon Bonaparte garb. The second sees Christopher faced with an intervention over his rampant drug use, only for the sit-down to devolve into a dysfunctional shouting match, and then a beating.

Collateral damage: the build-up to Adriana La Cerva’s demise was excruciating (HBO)

8. Season five, episode 12: “Long Term Parking”

Of all the deaths in The Sopranos, none hit harder than Adriana La Cerva (Drea DiMatteo), Christopher’s pitifully out-of-her-depth fiancée. Adriana was coerced into becoming an FBI informant back at the start of season four, with the pressures of a double life slowly tearing her apart. In “Long Term Parking”, the plotline’s slow-burn fuse finally reaches the dynamite, as Adriana attempts to flip Christopher into cooperating. It’s not like Tony and Co were redeemable until this point, but the shocking episode lurches the series into the even grimmer, more cynical tone of its final seasons.

7. Season six, episode 21: “Made in America”

As the show careened towards its endgame, The Sopranos leaned a little more liberally into conventional crime drama. Much of this concerned the escalating gang war between the New York mafia, led by Phil Leotardo (Frank Vincent), and Tony’s Jersey branch. “Made in America”, the final episode of the series overall, sees the drama play out to its bloody conclusion, leaving Tony as one of the last men standing. What happens, next, of course, is the stuff of TV legend: the series ends with the Soprano family gathering in a diner, culminating in a sudden and ambiguous ending. There’s no resolution here – for Tony or the viewers. Was it frustrating? Obviously. But so, so ballsy. Twenty-five years on, it’s impossible to imagine it ending any other way.

The Soprano family meet for dinner in final episode Made in America

6. Season two, episode 12: “The Knight in White Satin Armor”

One of The Sopranos’ more ingenious ideas was to shift climactic twists – “whackings”, power struggles and whatnot – to the penultimate episode of each season, allowing the finale more space to decompress and respond. By the later years, fans had grown wise to the trick, but back in season two, they were caught forcefully off-guard when Janice (Aida Turturro) shot and killed despicable husband-to-be Richie (David Proval) following an argument at the dinner table. Viewers who had been slowly gearing up for Richie to meet his end at the hands of Tony were utterly thrown by both the manner and abruptness of the killing. In this moment, The Sopranos became a show where seemingly anything could happen.

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Gunned down at dinner: Richie’s final moments before meeting his fate at the hands of his wife-to-be (HBO)

5. Season three, episode six: “University”

Part of the genius of The Sopranos’ approach to storytelling lay in its mastery of structure, both across seasons and within individual episodes. “University” was one of many episodes to make deft use of parallel storylines, juxtaposing the tragic murder of Bada Bing stripper Tracee (Ariel Kiley) with the struggles of Meadow’s college roommate (Ari Graynor). To this day, it’s a brutal watch, cementing Ralph Cifaretto – played by the great Joe Pantoliano – as one of the series’ most loathsome figures.

4. Season five, episode 13: “All Due Respect”

Yet another one of the best season finales ever, the conclusion to season five is a consummate example of the show’s many strengths. Old plotlines come to a fore – including the rift between the New York mob and Buscemi’s Tony Blundetto – and new ones are seeded, namely the arrest of the deliciously snaky mafioso “Johnny Sack” (Vincent Curatola). The image of Tony emerging bearlike from the backyard thicket, having fled the FBI on foot, is one of the series’ enduring visual metaphors, while the recurring intrusion of Van Morrison’s “Glad Tidings” exemplifies the show’s scalpel-sharp use of music.

3. Season three, episode 11: “Pine Barrens”

In recent years, The Sopranos – once touted as one of the darkest programmes around – has increasingly been heralded for its comic ingenuity, via a multitude of social media meme accounts. But The Sopranos has always been funny. And there’s no finer example of the series’ capacity for laughs than “Pine Barrens”. Directed by future series star Steve Buscemi, the episode sees Christopher (Michael Imperioli) and Paulie get lost in the New Jersey woodlands, having tried and failed to murder a runaway Russian mobster. It’s a brilliant, absurd and unpredictable episode, showcasing pretty much all of the series’ greatest strengths.

Worried wise guys: Christopher and Paulie get lost in the woods in one of the show’s best episodes (HBO)

2. Season four, episode 13: “Whitecaps”

An absolutely blistering hour of television anchored by two never-better performances from Gandolfini and Falco, “Whitecaps” sees the Sopranos’ marital problems come to a furious head. The long, intense argument is rendered with painful authenticity, as the secrets Tony and Carmela have been burying all season – his hidden money, her lusting after ponytailed beefcake Furio – come spitting out with a vengeance. It’s a captivating hour of car-crash TV, punctuated with a quintessential Sopranos punchline as Tony takes out his frustrations in a petty real estate dispute.

1. Season one, episode five: “College”

Just five episodes into its first season, The Sopranos was already making a case for its position at the top of the TV pantheon. “College” took the narrative away from the New Jersey criminal underworld, as Tony takes daughter Meadow (Jamie-Lynn Sigler) on a trip to Maine to look at prospective universities. A chance sighting of a former mob snitch takes Tony on a murderous detour, and results in one of the most compelling and unexpected hours of TV ever made.

‘Are you in the mafia?’: Meadow and Tony take a trip in the brilliant season one episode ‘College' (HBO)

‘The Sopranos’ is available to stream in the UK on NOW and Sky

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