The Sopranos was a TV show that aimed to capture life in all its unpredictability, mundanity, tragedy, and hilarity. Sure, it's about the leader of a crime family, Tony Soprano (James Gandolfini), but it's also about his life outside the crime world he operates in professionally. Tony — and all the other characters on the show - are shown to be believable, well-defined people who all have their flaws, personal struggles, low points, and victories.
That The Sopranos can have so many characters do so many terrible things while still making viewers care for (at least some of) them is a testament to the show's craft and its talented cast. For as horrific and sad as The Sopranos could be, it was also very funny sometimes, whether through dark comedy, absurd humor, or witty banter between its characters. The following episodes are some of its funniest and are ranked below by IMDb score.
10 "Moe n' Joe" (2006)
IMDb Rating: 8.1/10
The first half of The Sopranos' sixth season had a subplot involving Vito Spatafore (Joseph R. Gannascoli), a member of Tony's crew. He goes on the run after his associates find out he's gay, which some members of the mob view as an unforgivable offense within their world. Our "heroes" and their business associates are far from bastions of progress and acceptance.
Vito needing to go on the run isn't funny by itself, but part of his attempts to live outside the Mafia in the episode "Moe n' Joe" proves pretty amusing. Vito attempts a day of working a real job and can't stand how boring it is, and how slow time seems to pass. It's humorous for how relatable it is, and because it shows how alien the idea of "honest work" is for someone in the mob.
9 "House Arrest" (2000)
IMDb Rating: 8.1/10
"House Arrest" is the calm before the storm: the third-last episode of the show's second season. The penultimate and final episodes of Season 2 shake up the show dramatically due to two back-to-back character deaths, but "House Arrest" is ultimately more light-hearted, at least comparatively.
Uncle Junior (Dominic Chianese) was a reliably comedic character for much of the show's duration. Seeing him struggle to adapt to life under house arrest in this episode can be fairly funny. Also great when it comes to humor is the episode's ending, where the gangsters are shown with little to do besides sit around their hangout and make small talk, a funny sequence that is also oddly humanizing.
8 "Luxury Lounge" (2006)
IMDb Rating: 8.2/10
There were plenty of surprising guest stars featured throughout the six seasons of The Sopranos, and two of the biggest came in the Season 6 episode "Luxury Lounge." Acting legends Lauren Bacall and Ben Kingsley appear as themselves, thanks to a subplot that involves Christopher (Michael Imperioli) traveling to Hollywood to kickstart production on a film he wants to make.
It's a testament to how big The Sopranos was near the end of its run that it could pull such esteemed guest stars. In this case, it also led to some great — and surprising — comedy, given that the episode ends with Christopher being his laughably petty self and mugging Bacall — an 82-year-old woman — for a gift bag she got for presenting an award earlier in the night.
7 "The Weight" (2002)
IMDb Rating: 8.4/10
In "The Weight," tensions around an off-color joke one character made about another's wife are almost at boiling point. Ralph's (Joe Pantoliano) taboo joke about Johnny Sack's wife brings two crime families almost to the point of war, given Ralph is associated with Tony's New Jersey crew and Johnny Sack's a prominent member of the New York crew.
It's less the joke that's funny but more how heightened and extreme the consequences are or could be. There's something darkly funny about how fragile their entire system is and how a single, seemingly one-off remark could potentially lead to the whole thing crumbling (though at the same time, it is also endearing that Johnny Sack sticks up for his wife, with his devotion to her remaining strong throughout the entire show).
6 "Pilot" (1999)
IMDb Rating: 8.4/10
The Sopranos felt slightly different in its first season than those that followed. The tone was a little more light-hearted, the main characters seemed less likely to die until at least Season 2, and a good deal of conflict within Tony's family was played for laughs, particularly when it came to scenes with his conniving and hilariously cranky mother, Livia (Nancy Marchand).
The pilot episode of The Sopranos emphasizes this comedic approach most blatantly, with the show feeling fairly evenly balanced between drama and comedy. The pacing, editing, and dialogue are a little more heightened and stylized, making it feel odd compared to other episodes but quite funny when viewed on its own terms.
5 "Commendatori" (2000)
IMDb Rating: 8.5/10
"Commendatori" is a Season 2 episode that stands out because much of it takes place in Italy. Tony and some of his crew travel to Naples to meet some associates from the old country and do business with them, all the while realizing how far removed from the Italian way of life they really are.
Christopher ends up spending all his time in his hotel room, Tony is the one who gets some degree of business done, and Paulie (Tony Sirico) finds himself hilariously out of his element while trying to bond with the locals. It's a strange but funny spin on a vacation-themed episode, with some decent (and ironic) fish-out-of-water humor.
4 "Boca" (1999)
IMDb Rating: 8.5/10
The first season episode, "Boca, " has two prominent storylines." One isn't particularly funny at all, involving a local soccer coach who has inappropriate relationships with his students and how the Jersey crew deals with it. The other one that puts Uncle Junior front and center is hilarious.
A rumor starts surrounding Junior and his girlfriend that causes great shame among the show's insecure men, given the apparent mafia-wide stigma surrounding what is and isn't considered masculine when it comes to sex with one's partner. There are some great innuendos and perfectly uncomfortable comedy, making "Boca" stand out as a particularly funny episode in the show's overall very funny first season.
3 "Stage 5" (2007)
IMDb Rating: 8.8/10
Similarly to how "Boca" juggled two storylines with different tones, "Stage 5" is a funny episode at times and, in other ways, one of the show's saddest hours. The scenes surrounding Johnny Sack (Vincent Curatola) are heartbreaking, but the show's earlier scenes concerning Christopher's movie finally being made and screened are quite funny.
That movie is titled "Cleaver," and it certainly looks as though it could qualify as a so-bad-it's-good movie. From Tony not realizing straight away that one of the characters is based on him to Carmine Jr.'s (Ray Abruzzo) immortal reference to "the sacred and the propane," the film-related stuff is all very funny, making the episode's contrasting tragic scenes hit even harder.
2 "The Strong, Silent Type" (2002)
IMDb Rating: 8.8/10
In Season 4, Tony and his associates attempt to give Christopher an intervention due to his increasingly dangerous behavior brought about by his drug use. Ordinarily, a scene of a prominent character in a TV show receiving a drug-related intervention would be a serious moment, but The Sopranos is not an ordinary show.
The intervention goes south instantly, making for another darkly comedic look at toxic masculinity. The men in Tony's crew just don't know how to empathize with Christopher, and he's similarly combative throughout, making a perhaps well-intentioned intervention explode into violence within minutes. Playing such a scene for comedy wouldn't work in most shows, but it does here and stands as perhaps one of The Sopranos' most famous scenes.
1 "Pine Barrens" (2001)
IMDb Rating: 9.7/10
"Pine Barrens" is the highest-rated episode of The Sopranos, according to IMDb ratings, and is widely considered its funniest, too. The episode sees Christopher and Paulie go on a seemingly simple job that goes disastrously wrong, with them eventually getting stranded in the woods and almost freezing to death.
Like with Christopher's intervention, it's not a situation you'd expect to be funny, but thanks to the tensely funny dynamic between Christopher and Paulie — and the fact that neither character is very likable — it ends up being hilarious. It captures their delusions and paranoia in stark, visceral detail, making viewers believe they're in genuine danger while also making it very easy to find humor in their misfortunes throughout the episode in a way that feels very Coen Brothers-inspired in the best way possible.