It’s not always easy to pin down what makes a great show also greatly rewatchable, but it’s apparent that The Sopranos is one show that really benefits from being revisited. Due to how much death and heavy themes it contains at times, it might not be definable as a comfort show by any means, and some episodes are difficult to revisit. Yet when The Sopranos is at its funniest or most mysterious/enigmatic, it can very much reveal itself to be one rewatchable TV show.
Across six seasons and a total of 86 episodes, The Sopranos explores the complicated life of Tony Soprano, a mob boss and father who suffers from frequent panic attacks, fellow criminals who want him dead, and non-stop family drama. It’s a heavy-going show at times, but it can also be surprisingly hilarious for a series that’s usually described as being a drama. Those funny episodes prove rewatchable, but so too do many of the episodes that dig deep into Tony’s state of mind or his frequently bizarre dreams. What qualifies an episode as rewatchable is subjective, sure, but the following episodes – ranked below from great to greatest – prove extra deserving of multiple watches.
10
“Boca”
Season 1, Episode 9 (1999)
While you still couldn’t quite call season 1 of The Sopranos a sitcom in the traditional sense, it did feel like it had more outright comedy than some of the later/more miserable seasons that had more death and despicable behavior from increasingly flawed characters. “Boca” is one such episode from the show’s first season that feels like one of its funnier hours overall, even if it’s also instrumental in setting up the explosive conflict of the season’s final few episodes.
There’d been continual tension between Tony and Uncle Junior throughout the first season, but things escalate when a certain taboo truth about Junior becomes widely known (that’s a PG-rated description). It’s funny that such a seemingly innocuous thing can lead to genuine strife and resentment, but The Sopranos was never shy about commenting on (and making fun of) ridiculous and self-destructive quasi-masculinity.
9
“Proshai, Livushka”
Season 3, Episode 2 (2001)
While there were many planned death scenes throughout The Sopranos, to the point where it felt like few were left standing by the end, one character’s death in season 3 came about because of a cast member’s passing. That character was Tony’s overbearing and malicious mother, Livia Soprano, whose actress, Nancy Marchand, sadly passed away between season 2 and season 3.
Marchand was too iconic to recast, so after giving the character one final (somewhat spotty) scene with the use of CGI, Livia’s funeral was depicted in the second episode of the third season, “Proshai, Livushka.” While many deaths in the show are melancholic in nature, it’s hard to feel too sad about Livia dying (beyond missing the way she drove conflict, admittedly; likable, on the other hand, she was not). The funeral ends up being tremendously awkward and sometimes funny, making it a great episode to revisit and “enjoy” if you’re fond of cringe comedy.
8
“The Test Dream”
Season 5, Episode 11 (2004)
Pivoting from a couple of aforementioned humorous episodes, certain parts of The Sopranos can also be richly rewarding to revisit because of hidden details and things that are hard to pick up on initial viewing. The appropriately named “The Test Dream” is one of the strangest and most dream-heavy episodes of the entire show, with 20-ish minutes of the episode’s 50-minute duration devoted to showing a variety of strange dreams Tony’s been having.
It wasn’t the first time an episode of The Sopranos conveyed a good deal of dreaming, and it certainly wasn’t the last, either. While it might be impossible to find meaning or symbolism in everything (some dreams are just weird and inexplicable, after all), it helps to go back to “The Test Dream” and other similar episodes to try and dig as much as you can from them… so long as you don’t mind some occasionally nightmarish and surprisingly unsettling imagery here and there.
7
“Join the Club”
Season 6, Episode 2 (2006)
While “The Test Dream” vaguely foreshadows certain events from the end of season 5 and also presents images that reflect Tony’s conflicted state of mind, season 6’s “Join the Club” has a whole bunch of dreams that play out and seem to show Tony in some kind of purgatory. The fact they’re coma dreams coming about because he’s just been shot might have something to do with that, admittedly.
There’s a faint sense of unease to those scenes here, but they’re also quite melancholic, with Tony having the persona of “Kevin Finnerty” in these dreams, and dealing with a prevailing sense of confusion and being lost. Contrasted with scenes outside the coma dream of Tony’s relatives and friends being distressed at the idea he might not pull through, and sure, “Join the Club” isn’t fun. But it does have a unique atmosphere for an episode of the show, and the coma dreams are fascinating to explore, analyze, or simply get swept up in.
6
“Mayham”
Season 6, Episode 3 (2006)
Following right on from season 6’s “Join the Club,” “Mayham” is the second and final episode dealing with Tony’s coma dream escapades as Kevin Finnerty. He finds some guidance toward a certain destination within this series of dreams, but as he approaches, he finds that what he’s headed towards looks more like an afterlife than ever before, suggesting even further that he’s been in a kind of purgatory.
A man who looks like his deceased cousin approaches him, and at a house he’s told to enter, he sees a figure who could be his deceased mother. It’s eerie, but also can be interpreted in different ways; it’s hard to know if anything or nothing would’ve “happened” to either Kevin or Tony should he (or they) have entered. Still, that level of mystery and the enigmatic feel of it all makes “Mayham” another richly rewarding episode to revisit, once again owing to the numerous and layered dream scenes.
5
“Kennedy and Heidi”
Season 6, Episode 18 (2007)
Season 6’s “Kennedy and Heidi” is rewatchable for the same kinds of reasons that season 3’s “Proshai, Livushka” was. To keep it vague, “Kennedy and Heidi” features the death of a main character whose demise had been a long time coming, and some would say deserved. It’s someone you’d expect Tony to be upset about dying, but if anything, Tony acts like a huge weight’s been lifted off his shoulders, and that leads to some dark/uncomfortable comedy throughout.
Tony’s misadventure in the wake of a tragedy that didn’t seem all that tragic to him is chaotic, a little funny, and then ultimately mysterious. He takes peyote and then travels out into the Nevada desert with one of many beautiful (and much younger) women he gets to know throughout the show. Then, while both laughing and possibly crying, he looks out over the landscape and declares that he “gets it” before the end credits roll. Just what was there to get, and did he really get it? Good luck finding an answer to this strange but unforgettable final scene without copious rewatches.
4
“Whoever Did This”
Season 4, Episode 9 (2002)
In “Whoever Did This,” Tony kills someone surprisingly suddenly, considering his other seven direct murders on the show tended to be at least a little more planned out. It’s the kind of murder that seemed like it would happen closer to the end of season 4, but when it happens during the fifth-last episode, it seems to take both viewers and characters alike off-guard. However, it’s not to the point of breaking the fourth wall or anything, but perhaps just finding some common ground by both sides leaning up against it for support while navigating some eventful situations.
Dark comedy ensues in “Whoever Did This” after Tony asks Christopher out of the blue to help him with a now-pressing body disposal, only the weather’s freezing, Tony’s been injured and was blasted in the face with insecticide, and Christopher shows up to help while under the effects of heroin. It leads to a bleak, unsettling, but also darkly humorous series of events while the pair methodically deal with getting rid of a dead body, and it’s another singular/unique episode in the show’s run worth revisiting.
3
“College”
Season 1, Episode 5 (1999)
“College” is sometimes looked upon as the most important episode of the first season of The Sopranos, if not arguably the most important of the entire show. It was the first episode where the main character of the show, Tony, was shown killing someone in cold blood, and the idea of this happening so early on in a show that could go on for years, while asking viewers to continue watching him, was revolutionary for the time.
It can be harder to appreciate now, in a world where protagonists like Dexter kill dozens throughout their show’s run, and when someone like Walter White in Breaking Bad also faces a similar situation regarding murder even earlier than episode 5 of season 1. But The Sopranos was radical for what it did, and sometimes, it takes a little insight into television back in the 1990s to appreciate what this episode goes for a little more, making it another hour of the show where going back to it can prove more fruitful than just watching it once.
2
“Funhouse”
Season 2, Episode 13 (2000)
The first main character death in a show is always going to be a shocking one, and that was the case for the final episode of season 2 of The Sopranos, “Funhouse.” Sometimes, the heightened drama of seeing such a thing unfold again can make it an episode worth going back to, but some might feel that seeing an at least partly sympathetic character bite the dust again would prove to be too upsetting to go through, as Daft Punk might say, “ONE MORE TIME”.
But that’s not all “Funhouse” has to offer, because it’s also another The Sopranos episode that has plenty of dreams. While the dreams were “normal” in “The Test Dream” and brought about by a coma in season 6’s second and third episodes, in “Funhouse,” the dreams are shown to be extra bizarre, funny, and scary because they’re caused by food poisoning. It’s a wild episode, featuring an event that changes the plot forever, plenty of fart/poop jokes, and genuine fever dreams; a Sopranos classic, really.
1
“Pine Barrens”
Season 3, Episode 11 (2001)
Though it might not have won the most awards out of any The Sopranos episode, when you ask one of the show’s many fans what their favorite single hour of the show was, there’s a good chance they’ll say “Pine Barrens.” Like many episodes of the show, there are a few different storylines going on here, but the funniest and most memorable revolves around Christopher and Paulie getting lost in the woods and running the risk of dying from the cold, all the while their personalities keep clashing.
This duo often made for a great deal of comedy (and some drama) whenever they clashed on the show, and they clashed often, never having a better shared episode than “Pine Barrens.” This episode contains many of the show’s funniest lines and sequences, and also proves easy to revisit because of how dramatically it’s shot; for as funny as the episode is, it also does a remarkable job at showcasing how eerie, cold, and dangerous the titular New Jersey Pine Barrens are.