To me, The Sopranos is one of the most rewatchable and poignant television series of all time. It contains a cast of some of the deepest and darkest characters ever on TV.
And some of the best writing of all time.
Today, I want to go over 11 of the episodes I think are the best in the series. They’re favorites of mine, so feel free to disagree. But these are the ones I constantly go back to when I’m waxing nostalgic about the series.
Let’s grab some gabagool and dive in.
1. “Pine Barrens” (Season 3, Episode 11)
‘The Sopranos’
Credit: HBO
When it comes to just the pinnacle of the series, I think this has to be it. The episode follows the misadventures of Paulie Walnuts and Christopher Moltisanti as they get hopelessly lost in the frozen woods of South Jersey while trying to dispose of a resilient Russian mobster who maybe gets shot in the head.
It’s a perfect metaphor for the entire series, where violence, comedy, and the idea of fate come into play.
2. “Whitecaps” (Season 4, Episode 13)
‘The Sopranos’
Credit: HBO
The entire series hinges on Tony and Carmela’s marriage, and this episode finally brings them to a head.
This episode features a series of devastating arguments, masterfully acted by James Gandolfini and Edie Falco, that feel painfully real.
You’re watching something disintegrate before you, and even though you know it’s better for them to go apart, you can’t help but want them to stay together.
3. “Long Term Parking” (Season 5, Episode 12)
‘The Sopranos’
Credit: HBO
Man, I think about Adriana La Cerva’s car ride all the time.
She gets totally caught between her loyalty to Christopher and the relentless pressure from the FBI, which is actually killing her.
Adriana’s desperate attempts to escape her predicament lead to a gut-wrenching conclusion where she learns the consequences of being close to the mob.
4. “College” (Season 1, Episode 5)
‘The Sopranos’Credit: HBO
This is probably the most important episode of The Sopranos, because it allowed the show to set the tone of the rest of its run.
We follow Tony as he takes Meadow on a college tour in Maine. The idyllic father-daughter trip takes a dark turn when Tony spots a former associate turned FBI informant, whom he eventually strangles to death.
It marks a solid turn for Tony into a guy who is willing to kill, we knew this about him, but this is our first visceral sense of what he’s willing to do. And we buy in.
5. “Funhouse” (Season 2, Episode 13)
‘The Sopranos’
Credit: HBO
Through a series of surreal and symbolic fever dreams brought on by food poisoning, Tony slowly comes to a horrifying realization that Sal “Big Pussy” Bonpensiero is an FBI informant.
The show was never afraid to do these weird, dream episodes that offered up a lot of exposition and ideas in new ways.
The episode leads to a chilling confrontation on a boat that remains one of the series’ most iconic moments.
6. “The Blue Comet” (Season 6, Episode 20)
‘The Sopranos’
Credit: HBO
Man, when I first watched this episode I stood up and cheered at the crescendo of violence and paranoia as the war between the New Jersey and New York crime families escalates.
The episode is a masterclass in building tension, with several key characters meeting their demise in sudden and brutal fashion.
It’s sort of the perfect ending to the story…that you know has to go even deeper in the finale.
7. “Whoever Did This” (Season 4, Episode 9)
‘The Sopranos’
Credit: HBO
Do we ever find out if Ralph Cifaretto set the stable fire that results in the death of Tony’s beloved racehorse, Pie-O-My? No. But we know he did it, and so does Tony.
It’s the perfect showing of rage inside of a man and how much he hates the unpredictable Ralph. The confrontation is a raw and brutal display of Tony’s simmering anger, and it leads to one of the best deaths in the series.
8. “Made in America” (Season 6, Episode 21)
‘The Sopranos’ Credit: HBO
The series finale of The Sopranos remains one of the most discussed and analyzed episodes in television history.
The final scene, with its cut to black, left audiences in a state of shock and has been the subject of endless debate ever since.
I think he’s dead; a lot of people think he’s just living in fear forever. It’s the absolute genius culmination of art.
9. “Kennedy and Heidi” (Season 6, Episode 18)
‘The Sopranos’
Credit: HBO
One of the magic things about the show is that toward the end, you start totally siding with Tony and wanting to whack people who are in his way.
The episode explores Tony’s complex and often contradictory feelings towards Christopher, culminating in a shocking act of self-preservation where he kills him.
It’s one of the most emotional and frustrating scenes in the whole series.
Don’t do drugs.
10. “Employee of the Month” (Season 3, Episode 4)
‘The Sopranos’
Credit: HBO
Look, this is an episode I actually skip during rewatches because it is so brutal. In it, Dr. Melfi is raped. The aftermath of her assault forces her to confront the core of her therapeutic relationship with Tony. She wants revenge, but she can’t bring herself to see someone murdered. It’s a fascinating exploration of morality and character.
11. “University” (Season 3, Episode 6)
‘The Sopranos’
Credit: HBO
This episode is a stark and brutal examination of the misogyny and violence that underpins the mafia world. It’s a masterclass in getting you to hate a person.
It juxtaposes the tragic story of Tracee, a young stripper at the Bada Bing, with the collegiate life of Meadow, in an amazing study of life and privilege.
The episode ends with a senseless murder of Tracee by Ralph Cifaretto, a moment that is a horrifying reminder of the characters’ capacity for cruelty. And it makes you want him to get what he deserves.
Summing It All Up
It’s so hard to pick when it comes to these episodes. I almost picked an entire season just to shake things up. This is a show that could have had like 50 episodes on this list.
I know there are ones I left off that you’ll be upset about, but I want to hear about it anyway.
Let me know what you think in the comments.
