There are so few comedies that hold up to multiple viewings while still being funny. Among 21st century shows, Community is up there with Curb, Arrested Development, and Happy Endings in this respect (maybe Wet Hot American Summer too), as well as in how strong and distinct its voice is -- which is exactly why season four stands out. If season four was all that existed, it would be a solid show, well-written, great actors. But you can't do Arrested Development without Mitch Hurwitz; you can't do Community without Dan Harmon. Losing half the cast by season six, when Pierce, Shirley, and Troy had all left for one reason or another, affects the basic core Community-ness of the show less than losing Harmon for a year did. (Of course, you could argue that the three characters most vital to that Community-ness were among the four who remained, but I don't think that dilutes my point.)
We owe Community's existence in large part to an era of diminished expectations and desperation at NBC, which also gave us Parks, Friday Night Lights (once DirecTV chipped in), and Chuck, all shows that performed pretty poorly in the ratings but not poorly enough to trump the value of their established audience vs. the risks of putting new shows on in their place, because hardly anything was prospering on NBC, so there was no real standard of performance other series had to measure up to.
I think I said when the sixth season was on that Britta was my favorite character, which remains true in rewatching. She may be my favorite sitcom character of all time -- she's certainly up there with Taxi's Reverend Jim, WKRP's Dr Johnny Fever, and Soap's Burt Campbell. The development of Britta parallels the course of the show, in a lot of ways: she is least distinct in the early days of the show, when it's a funny, well-written sitcom in which many of the characters are not fully in focus yet (Troy and Annie are fairly insubstantial sketches, Britta is primarily the hot girl Jeff wants to impress and/or fool, and is overall more serious). Jeff is Jeff from day one. He grows, sure, but in the way that all sitcom characters in his situation grow: he becomes less of an asshole to people he has come to know better. Abed, similarly, is pretty much Abed right away, becoming more nuanced over time, but not in a way that makes his early episodes seem out of character. Britta is the one who doesn't just become more flawed over time, but flawed in ways that become the main way other people characterize her ("Britta is the worst," "The AT&T of people"), with her "I lived in New York," her empty and performative activism, her ambitions to become a therapist. But she also becomes goofier, with more physical comedy and weird tics that are perfectly consistent -- it somehow makes more sense for Britta to be the one who says "baggle" than anyone else, for Britta to have a carnie ex-boyfriend and parents played by Martin Mull and Lesley Ann Warren.
Dean Pelton is the only one who goes through quite the same level of development -- at least successfully, since Chang is used for different purposes in different seasons. In Chang's case it turns him into an unwieldy, unwriteable cartoon, but the Dean becomes both broader and more human.
Anyway, I couldn't resist making a quick list of my favorite episodes. They are in chronological, not ranked, order.
Spanish 101 (season 1, episode 2)
This was one of the great things about rewatching Community: one of the best episodes is the second episode. No, the series hasn't come fully into focus yet, especially when it comes to Troy, Britta, and Annie. But early Chang is probably still the best incarnation of Chang, who becomes not just cartoonish but an active nuisance later in the series and goes through multiple periods in which he is weirdly infantilized. While Dean Pelton -- my second favorite character after Britta -- becomes more interesting and more funny as time goes on, Chang was best as a minor supporting character. What makes this episode is the Jeff/Pierce relationship -- which would always be at its best when played like this, with Pierce's hero-worship of Jeff (and later, Jeff's realization that he will some day be as uncool as Pierce).
Contemporary American Poultry (season 1, episode 21)
After toying with tropes and the characters' awareness of tropes in subplots, this is Community's first full-on homage episode, riffing on Goodfellas in a story about the corruption that comes with power over the cafeteria's chicken fingers.
Modern Warfare (season 1, episode 23)
The first paintball episode probably remains the best, but this episode gets bonus points for the fact that even its sequels were pretty fantastic -- there were absolutely diminishing returns in the paintball episodes over the course of the series, but when you start with such a high point, it takes a while before those diminishing returns bring you low.
Epidemiology (season 2, episode 6)
The zombie episode! Brilliant all the way through, but especially in its use of the cat scare, and of Jeff's ridiculous vanity.
Advanced Dungeons and Dragons (season 2, episode 14)
The fact that Community has two D&D episodes, both of which are good, when the show isn't a show about nerds or geeks like The Big Bang Theory or something ... is ridiculous. The first one is the best of them, both for the way it fits with the season's ongoing character arcs and for Alison Brie's miming, but if the first one didn't exist the second one would be on this list.
Intermediate Documentary Filmmaking (season 2, episode 16)
Out of all the main characters, Pierce-focused and Shirley-focused episodes are the rarest (depending on how you count "Troy and Abed" episodes). Most of them are not among the show's best -- Harmon doesn't seem to have had much of a handle on Shirley (her best scenes are rarely those in which she is the main character of the story, unfortunately), whereas with Pierce, the problem was the opposite. He seems to have understood the character perfectly well -- and made him so petty and unlikeable that, like Chang later, it's often difficult to understand his presence in the show or among these people. This episode is one of two that revolve around Pierce giving everyone a gift with ulterior motives -- and while he is no less petty here than usual, the format is a good occasion to explore his relationship to and impressions of each of the other characters. This leads to some great stuff -- Troy's panic is the most obvious, but Britta's ethical dilemma over Pierce's check is classic too.
Critical Film Studies (season 2, episode 19)
The Pulp Fiction/My Dinner With Andre episode. I mean, what more can you say? It's pitch-perfect, from the choice of those two particular movies (can you think of two indie movies that are less alike, while at the same time both being renowned for their talkiness?) to the continuation of Abed's Cougartown fandom.
Paradigms of Human Memory (season 2, episode 21)
The back half of second season really demonstrates Community's brilliance, and of course the stuff that would make it so divisive. This is a clip show in which all the clips are from study group adventures we haven't seen. It's such a brilliant concept that it's amazing it hasn't been used frequently enough for us to have been sick of it by the time this episode aired, but I can't think of a live-action show that had done it before.
Remedial Chaos Theory (season 3, episode 3)
The episode that introduces the darkest timeline, but there are so many other great moments apart from that, the best of which might be the realization that the happiest timeline is the one where Jeff leaves the room and his absence leads to everyone else feeling happier and more relaxed.
Digital Estate Planning (season 3, episode 20)
The eight-bit episode, which would be on this list even if only for Annie and Shirley's murder spree, but which also features Abed's eight-bit girlfriend.
App Development and Condiments (season 5, episode 8)
Because Harmon never developed Shirley as deeply as some of the others, her religious self-righteousness that was established early on -- and somehow never goes away even as she's fleshed out more and humanized -- is good fodder for episodes like this one, which positions her as an antagonist. Plus, hey, Mitch Hurwitz as Koogler.
Basic Crisis Room Decorum (season 6, episode 3)
The best parts of season 6 are the Britta parts, as she reaches her final evolution as a ridiculous goof. Basic Crisis Room Decorum features Britta shitting her pants and running around in panic, and the first mention of 90s alternative band Natalie is Freezing. This episode is so much better than I make it sound.
Queer Studies and Advanced Waxing (season 6, episode 4)
Dean Pelton's sexuality is front and center, and actually thoughtfully handled in Community's own weird way, rising above making him the butt of a joke about it.
Honorable mentions:
Comparative Religion (season 1, episode 12). It's not quite in the upper echelon, but major bonus points for Anthony Michael Hall (who I wish had returned) and the holiday brawl.
Physical Education (season 1, episode 17). The billiards episode, which features some of first season's best moments of physical comedy.
Aerodynamics of Gender (season 2, episode 7). The mean girls subplot isn't good enough to make this one of the very best episodes, but the transcendent trampoline with its racist guardian is fantastic.
Abed's Uncontrollable Christmas (season 2, episode 11). The stop-motion is terrific, but the novelty wears off on re-watches, and the writing isn't as strong as the novelty.
Horror Fiction in Seven Spooky Steps (season 3, episode 5). The Halloween anthology episode -- a little uneven by Community standards, but certainly great.
Studies in Modern Movement (season 3, episode 7). I don't know what episode better shows how much Troy's character was developed from the beginning of season 1, when he was the ex-jock Annie had a crush on; here he's Abed's childlike playmate, the two of them a couple of Oscars to Annie's Felix. The Dean/Jeff subplot is pretty great.
Introduction to Teaching (season 5, episode 2). Invaluable for Abed's Nic Cage, if nothing else.
Emotional Consequences of Broadcast Television (season 6, episode 13). The Community finale is also one of its most meta episodes, but suffers from the lack of half of its original cast.
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