The cast of 'The Sopranos'

‘The Sopranos’ at 25: Revisiting the 10 Best Episodes

On January 10, 1999, about 3.4 million viewers tuned into HBO’s new mobster show, The Sopranos, and witnessed the birth of a television program so worshipped, it changed the way we think about television as a whole.

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The show ran for six seasons, ending with one of the most discussed series finales of all time on June 10, 2007. The David Chase series won 21 Emmy Awards during its run, and it remains one of Max’s most popular streaming titles even 25 years later.

Yes, that’s right. The Sopranos turns 25 this month, so here’s a refresher of some of the episodes that cemented the series’ legendary status. Here are the 10 best episodes, ranked to the best.

10. “Irregular Around the Margins”

Season 5, episode 5

Adriana (Drea de Matteo) points a finger at TOny Soprano (James Gandolfini)
(HBO)

While commiserating over their health problems—a cancerous mole removal for Tony Soprano (James Gandolfini) and irritable bowel syndrome for Adriana (Drea de Matteo)—the pair come dangerously close to starting an affair that would prove disastrous for all involved. Instead, they have a car accident while trying to score drugs, and Adriana winds up hospitalized. The crew makes up salacious rumors, and next thing you know, Christopher (Michael Imperioli) is furious and looking for revenge.

Nothing good can come of picking a fight with Vito (Joseph R. Gannascoli) or trying to attack Tony at the Bada Bing, but Chris does it anyway. He also roughs Adriana up and relapses on heroin. It’s a wild ride, but the end reminds us that family is family, even when they fight.

9. “The Blue Comet”

Season 6, episode 20

Johnny Sacks (Vincent Curatola) smoking a cigarette in The Sopranos
(HBO)

This is the second-to-last episode in the entire series, and it’s the culmination of years of grievances and simmering subplots. Dr. Melfi (Lorraine Bracco) finally tells Tony that their seven-year therapy relationship is over. Uncle Junior (Dominic Chianese) is broke, and Tony refuses to finance his nursing home (Junior did try to have him killed, after all). Most importantly, the mob war that’s been brewing between the New Jersey and New York crews finally boils over, leading to a number of major characters meeting shocking deaths. Even the FBI’s Agent Harris (Matt Servitto) warns Tony that he’s in danger, which is saying something!

8. “Funhouse”

Season 2, episode 13

Tony and the crew prepare to kill Big Pussy in The Sopranos
(HBO)

Since the first episode, Salvatore “Big Pussy” Bonpensiero (Vincent Pastore) was one of Tony’s most loyal soldiers. Then Pussy started ratting to the feds, even trying to act like one of them in a bizarre form of Stockholm Syndrome. Everything catches up with him at the end of season 2 when Tony has a delirious fever dream caused by food poisoning and has a premonition about his friend. “You know I’ve been working with the government, right Tone?” Pussy, in fish form, tells Tony in his dream.

Later, Tony, Paulie (Tony Sirico), and Silvio (Steven Van Zandt) take Pussy for a boat ride. Four men leave the dock, but only three return.

7. “Pie-O-My”

Season 4, episode 5

A painting of a general (James Gandolfini as Tony Soprano) standing with a horse
(HBO)

Things are unraveling for Adriana, who is being pressured by the feds to wiretap her bar. She starts to doubt whether Richie (David Proval) and Pussy really left for “witness protection,” as she was told. Meanwhile, Tony becomes part-owner of a race horse called Pie-O-My with Ralphie (Joe Pantoliano), who doesn’t love sharing his winnings with the boss. In the end, Ralphie refuses to give the horse veterinarian treatment, so Tony rushes to the stables to comfort the sick animal. We see the same unexpected tenderness Tony showed to those silly ducks in season 1, and more importantly, this episode sets up the action for episode 9, when Tony snaps and kills Ralphie after Pie-O-My dies in a suspicious barn fire.

6. “Everybody Hurts”

Season 4, episode 6

Tony Soprano (James Gandolfini) threatens Gloria (Annabella Sciorra) in The Sopranos
(HBO)

Tony has been carrying on a volatile affair with a woman he first saw in his therapist’s waiting room—what could go wrong? Things come to a head when Gloria (Annabella Sciorra) takes her own life, and Tony compensates for his guilty conscious by being over-the-top nice to everyone around him. He taps Christopher to step up and be more of his right-hand man, but Chris is in the midst of a staggering heroin addiction. Elsewhere, restaurateur Artie (John Ventimiglia) starts a fight he can’t finish and has to ask Tony for help. This episode was written by Imperioli and directed by Steve Buscemi, and it’s a unique look at how Tony is the “fix it guy” for everyone in his orbit.

5. “Long Term Parking”

Season 5, episode 12

Adriana (Drea de Matteo) and Silvio (Steven van Zandt) driving in The Sopranos
(HBO)

So much happens in this episode! First, Tony is confronted with a major problem with his favorite cousin from childhood, Tony B. (Steve Buscemi). Johnny Sack (Vincent Curatola) is minted as the new boss of the New York Lupertazzi family, and now they want revenge on Tony B. for a long ago beef. Phil (Frank Vincent) is going to do terrible things to Tony B. unless Tony can get there first (which he does in the next episode, the season 5 finale.)

Most importantly, Adriana comes clean with Christopher, who’s so enraged he almost kills her on the spot. But that’s not how they do things, is it? Instead, they concoct a story to get her into a car with Silvio, who drives her out into the woods and, well, you know.

4. “Pine Barrens”

Season 3, episode 11

Christopher (Michael Imperioli) and Paulie (Tony Sirico) looking cold in The Sopranos
(HBO)

In another episode directed by Buscemi, Chris and Paulie get seriously rumpled when a run of the mill whacking goes awry. It’s the first, and possibly last time we ever see the impeccably-coiffed Paulie lose his cool, and with good reason: they’ve managed to lose an injured Russian mobster in the middle of a pine forest in winter. After spending a terrible night outside, they’re eventually rescued by Tony and Bobby (Steve Schirripa), and the men silently agree to lie to their boss about what happened.

3. “College”

Season 1, episode 5

Jamie-Lynn Sigler and James Gandolfini in The Sopranos
(HBO)

We were still getting to know the Soprano family when this episode arrived, and it changed the way we looked at Tony forever. While escorting Meadow (Jamie-Lynn Sigler) on a college tour in Maine, Tony spots a man who disappeared before paying back the money he’d borrowed from the family. Even though Meadow is right there, Tony manages to chase the guy across a college campus to beat him up. It’s the first time we see Tony get his hands dirty, and it’s jarring to see it happen in such an innocuous place.

2. “The Knight in White Satin Armor”

Season 2, episode 12

Tony Soprano (James Gandolfini) and his sister Janice (Aida Turturro) in 'The Sopranos' season 2, episode 12 "Knight in White Satin Armor"
(HBO)

Hell hath no fury like a Soprano scorned! Junior and Richie have been plotting to have Tony murdered, but when Richie fails to garner support among the crew, Junior rethinks it and tells his nephew about the hit instead. Tony immediately starts plotting to take Richie out, but his sister Janice (Aida Turturro) gets there first.

You see, Janice and Richie are planning their wedding, but there’s just one problem: Richie is a misogynistic heathen who doesn’t think twice about popping her in the face when she gets on his nerves. That sort of thing doesn’t fly with Janice, who leaves the room and comes back locked and loaded. There’s something so satisfying about watching this cretin die.

1. “Made in America”

Season 6, episode 21

Tony Soprano (James Gandolfini), Carmela (Edie Falco), and AJ (Robert Iler) in the diner in the Sopranos series finale
(HBO)

Welcome to the last Sopranos episode ever! Showrunner David Chase took the helm with this one yet again, producing what is inarguably one of the best series finales of all time. Tony tries to make peace with New York after the carnage of the previous episode, and he learns he may face criminal charges thanks to an informant. Phil meets a grisly end, Paulie takes over Richie’s gang, and Tony says goodbye to Silvio and Junior.

In the final scene, the Sopranos meet at a diner for a meal. Tony keeps glancing at the door, waiting for Meadow to arrive. We see her park her car and open the door to the diner, but when the bell on the door rings as it opens, the screen abruptly cuts to black. The end.

People speculated about the ending for years, but in a 2018 interview with The Hollywood Reporter, Chase cleared up the confusion: That wasn’t Meadow who entered the diner … Tony gets whacked.

The Sopranos GIF - Find & Share on GIPHY
(HBO)

“I had no idea it would cause that much … of an uproar,” said Chase. “What was annoying was how many people wanted to see Tony killed. They wanted to see him go face-down in linguini, you know? That bothered me.”

Happy 25th to this iconic series! Check out all of the episodes, streaming on Max.

(featured image: HBO)


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Beverly Jenkins
Beverly Jenkins is a contributing entertainment writer for The Mary Sue. She also creates calendars and books about web memes, notably "You Had One Job!," "Animals Being Derps," and the upcoming "Mildly Vandalized." When not writing, she's listening to audiobooks or streaming content under a pile of very loved (spoiled!) pets.