I really struggled where to rank this. I added sketch shows to my rankings mainly for one sketch show still to come way up the list. But I Think You Should Leave (ITYSL) really is that good, and more than that, it is that original. There is no show that reaches its level of abject silliness and hilarity. There is no show that I've seen that can mine so much out of being propestorous, and awkward, and weird. There is an underlying weirdness that surrounds everything about ITYSL. It has some of the greatest sketches of all time - seriously. At its best, in can compete with that sketch show to come. I don't feel that it is heresy to say that. The Darmine Doggy Door, the 55 burgers...., the Dan Flashes. And of course Coffin Flop. It also has this incredible core of returning characters and returning actors, creating this little, mystical, stupid little world for us all to enjoy sketch after sketch for years.
9.) What We Do in the Shadows (FX)
Comedies in general have really disappeared in recent years. Every show ahead of this premiered in 2014 or earlier. None made it to 2020 (except for one grandpa show - I think you know which). What We Do in the Shadows was the one holdout keeping true to comedy. This wasn't a drama hiding behind a few laughs (cough** The Bear**cough). This was an out and out comedy, that took an amazing premise - what if Vampires existed, but they were basically just normal people that could only really live at night - and made it into something so beautiful. The characters so well acting out just amazing material (Matt Berry's line readings - "New Yorkkk Citaaaay"). Everyone playing absurd so straight. The incredible moments like the running gag of the other vampire crew, to the best use of Kirsten Schaal ever. I do worry this is about as good as comedy would get in the 2020s.
I don't know if any show in the last ten years has been funnier than the final season episode where they create teh fake Rail company to cheer up a neighbor. It was taking a normal What We Do premise to 11, and running it so straight, so earnest, that it still remained so beautiful. Also, everything about Colin Robinson being an energy vampire was played so well also. I loved that there wer no real stakes, that they would just figure out some Deus ex Machina to bring the core group all back together again - a vampire version of Seinfeld if you will. Gone is What We Do in teh Shadows. Hopefully something can take its place as a true comedy great for the back half of the 2020s.
8.) Bojack Horseman (NETFLIX)
A few years back, Alan Sepinwall ranked his top shows to come out of the Streamers - probably say at the 10-year mark of Streaming Services. His #1 was Bojack Horseman - a show he called the only true out and out classic a Streaming service created. Now this was before AppleTV really started in earnest (though I'm not really a watcher yet), but I would still argue that likely remains true (though admittedly I have a NETFLIX drama at a higher spot). Bojack was just so damn creative, so incredibly shart, smart and emotionally weighty. It took advantage of its ridiculous premise of a world where anthropromorphic animals lived with humans, and mined that for visual gag after verbal gag after outright dialogue gag for season after season. And of course, it was one of teh more emotionally weighty shows on TV as well.
Much was written about how sad, somber, introspective and, well, dramatic Bojack was at its best, but at the end of the day, it was never not a comedy. The intention was you would laugh - even as it tackled mass shootings, abortion, homelessness and depression in about ten different ways. It would keep you laughing by some pun (no show used puns better), some line, and some delivery by a truly amazing cast of voice actors. I don't know if this was Will Arnett's best role (GOB will be hard to top) but the fact that it comes close says something. Amy Sedaris is brilliant, and this is up there. Aaron Paul was amazing. Everyone was amazing dammit - maybe no one moreso that Raphael Bob-Waksberg the creator and the other writers who used every inch of background cartoon space to tell side jokes (e.g. while an Americrane Airlines flight was "delayed", a Turkish Airlines flight was "deflated"). Bojack was sad at times, but it was funny at all times. And for that, I truly love it.
7.) Nathan For You (Comedy Central)
Because of The Rehearsal, and the Curse, and the general stickiness of the best episodes, it is hard to remember that Nathan For You aired a long, long time ago - mostly in the first half of the 2010s. Probably for the best, because the internet became even more omnipresent that he probably couldn't rope unaware small business owners by 2018 or so. Hell, even by its final season it was clear he couldn't given how more episodes turned into examining the mystery of Fielder's own psyche and imperfections, than the zaniness of its central conceit. But let's not forget just how amazing that conceit was - how so many of these ideas actually kind of made sense on paper (start a moving company with 200 employees to be able to pack up a house in as little time as possible). You can basically split Nathan For You into two parts - one being the true fake zany business consultant, and the other as introspection into human psychology, and both were amazing.
They were both amazing from Day 1 by the way. On the introspection side, while that got more notoriety as the show went on (e.g. episodes like Finding Frances to end the show period), that was at the heart of the much ballyhooed Season 2 episode focused on the gas rebate voucher and the extent people would go - to revealting secrets on a midnight hike - to save a few bucks. Of course, the other sketch in that episode was him convincing a beach caricaturist to draw exceedingly offensive caricatures as a marketing campaig. There's your ying and yang in the fourth episode of the show period. Nathan Fielder has increasingly revealed himself to be a genius, but also a deeply weird individual who appears to be more and more not acting but just playing himself. The dials were optimized with Nathan For You however.
6.) Everybody Loves Raymond (CBS)
There were many great 90s sitcoms - or ones at least believed to be great at the time. One of them is higher up the list - and I think you know which one that is. Everybody Loves Raymond was fantastically popular at the time, but probably took a backseat to both Seinfield and Friends. And as we'll see, I think it still has a backseat to Senifeld, I think it's aged so well - mainly because it was a perfect hybrid show - it was absurdist, it was sharp, it was caustic, but within traditional grounds. Parading within the context of an old timey sitcom of a man, his wife, his kids, his siblings and his parents, was a show that was so much more glorious and sharp than that. They portrayed the familiar, but put a whole new slant, a whole different energy behind it.
Years later as we've seen Ray Romano really shine as an actor, it makes sense that he was super strong at this point already. But what makes the show really sing is all the other people that were just magnetic. Frank and Marie are two of the great sitcom characters ever. Debra was far funnier than just being the token wife to annoy Raymond (it is amazing how many times they made her outright more funny and more right than Ray). Of course Brad Garrett was a revalation. The side characters were great. This was a 21st Century sitcom hiding within the foundation and structure of a mid-20th Century one. The best natural progression from the Honeymooners or some shit. Just a gem of a family sitcom. The absolutely apex of that genre.
5.) Veep
What's weird about Veep is it started in Obama's first term. Granted, it was in 2012, so only a few months before his re-election, but it was at a time where for the people watching teh show, they probably were pretty happy with how politics were going, all things considered. It ended in the Trump term, where real news of the administration probably makes early seasons of Veep seem quaint. But Veep never lost its plot, never lost its drive, its focus, its causticness, even as it turned the ridiculousness up to 11, because reality turned itself to nine. But let's move away from politics, because this show wasn't really about that. It was about insulting people over and over and over again in the best ways possible.
Of course, it was also about Julia Louis Dreyfus getting a role just perfect for her skills. Granted, everyone in the cast was perfectly placed and perfectly graet at reciting biting, filthy, cutting commentary and barbs from the twisted mind of Armanda Ianucci. Also, and i'll never stop giving Veep credit for this, it somehow get better and more funny when it elevated Selina to being President in the end of Season 3 and through Season 4-5. It somehow became funnier when the actual plot beacme, in a way, more meaningful (let's remember a long running point in the first two seasons was how of little import a Vice President really well). The show get better for it. Selina got better for it. Dan and Amy having to become failing lobbyists were better for it. And of course anything with Jonah Ryan, and the dueling brilliance of Ben and Kent. Veep was truly just a masterpiece of a show, that at its best (that same S3-4 stretch) was easily one of the best things on TV, period.
4.) It's Always Sunny in Philadelphia
What can you even say about this show - I only jumped on board watching live episosdes in Season 6. For most shows that would be coming in late. For this one, it is coming in in what will liekly be its first third when it's all said and done. Yes, the show in later years is a bit more forgettable - I can't name at gunpoint what episodes were in season 13 or Season 15 vs my ironclad memory of what was in Season 5. But still, the fact there is a Season 13, a Season 15, a soon to be Season 17, and in reality there will be as many seasons as Rob, Charlie and Glenn want there to be at this point. They've solved TV in a sense - this is their world until they want to relinquish it.
There was a study a few years ago that revealed that It's Always Sunny has the smartest viewership of any sitcom, and why not? Because behind the sophomoric hijinks hides a show that has been far smarter, far more caustic, far more satiric than people think. Recent years have highlightted that more and more, as they've turned Mac into a proudly openly gay man, and Charlie finally found his dad and whatnot, but hell the second episode they ever did took a spear to the abortion debate. They were never afraid of trying to give their take on any type of situation. They skewered reality TV, gay marriage, curse words, north korea, politics, gang violence, and so much more - keeping it with these four idiotically brilliant people and a small cast of rotating geniuses.
Always Sunny in simultaneously the most underground, low budget show of all time, and the grand-daddy of sitcoms that has literally set records for its longevity. It first aired in literally 2005. It's going to release its 17th season in 2025 - a good sign that it rarely took years off. It's also far more scripted than you think - the amazing shouting, insults, yells, boisterousness, all a part of a strange brew that works in the heads of these three guys in Rob, Charlie and Dennis that will hopefulyl never really abate. It sounds morbid, but I truly hope that Always Sunny ends with Danny DeVito's death - it means they wrang every last drop of brilliance out of the folks at Paddy's before calling it a day.
3.) Chappelle's Show
Dave Chappelle is such a prolific standup, and at this point such a notorious standup, that it may be hard to remember that years ago he was the centerpiece of an all time great sketch show - a completely different medium than standup. He had help, of coruse - from co-creator Neal Brennan, to a host of recurring actors that were just brilliant (Charlie Murphy, Donell Rawlings, Paul Mooney, etc.). But Chappelle's Show was about Dave (and Neal) and it was just amazing. Very few episodes really focused on race relations - it focused on just lampooning everything - from Making the Bad, to Rick James, to the Jury Selection Process, the Reparations, to so much more. The best way to describe the shows intentions is that it was literally their first episode that the Clayton Bigsby black white supremacist sketch aired. They came out the gates swinging, and didn't stop for 2.25 seasons.
Dave ended the show at in theory the right time, when he felt the world was focusing on the wrong parts of his amazing creation. He did leave behind three or so half baked Season 3 episodes that were stitced together with Charlie Murphy and Donell Rawlings playing the Dave MC role - and even in those episodes, it was so clear that Dave was far from done. Case in point: the now oft rememberd Tupac song palys in a club sketch ("I wrote this song in '94...") was in those half baked episodes.
But it was the amazing second season, the incomparable second season, that locked Chappelle's Show place in history. Of course, there's the two Charlie Murphy True Hollywood Stories sketches, including the Rick James one which while oft cited, is absolutely the funniest ten minutes ever filmed. But there's so much more as well, from I Know Black People, to The Racial Draft, to Making the Band, to the amazing Black Bush - the final sketch aired with Dave MC-ing. The show was great because it didn't always need to lampoon politics, or race. Some of the best sketches were just pure comedy for comedy's sake - like much of Rick James, or The Playa Hater's Ball, but as it opened with Clayton Bigsby and closed with Black Bush, it was so clear when it wanted to take about race, about politics, it could do that as well as anyone ever as well.
2.) Arrested Development
Technically, I'm including the two NETFLIX seasons, the second one (fifth season overall) being really forgettable. I'll always say the 4th Season, especially when watched in the recut 22-episode version, is
almost underrated at this point. But at the end of the day, this is about this first three seasons, to me the greatest contained stretch of comedic television ever. My one show ahead of it beats it on longevity - and that show should be patently obvious at this point. Bit in terms of peak, you could easily argue this is the best sitcom ever. Honestly, I feel that way. No show combined everything you want out of a smart comedy. Straight funny punchilnes, visual gags, incredible physical work, incredible wordplay, all-time level of callbacks and references taht paid you off for watching week to week. It was a master of the form in every way, and it starts with two things it did better than basically any other show: it's tone, and it's long list of characters.
The characters are the more obvious areas - you had one of the all time great straight men in Michael Bluth. You had two of the better goofball characters in Tobias and GOB (and add Buster to that too). You had maybe the funniest single sitcom character of all time in Lucille Bluth. You had so many more as well. There was no weak link in that main cast (basically the people introduced in the intro), and the recurring characters go 20 deep of excellent performances, excellently written without blinking - you can just rattle them off, from Maggie Lizer, to Barry Zuckerkorn, the Warden Gentiles, to Marta, to J. Walter Weatherman, to Kitty Sanchez, to Rita Leeds, to so many more. Only maybe the show at #1 wrote guest / recurring characters better.
And then there's the tone - the weird quasi-mockumentary of it all. The never ending narration from Ron Howard. The incredibly straight way the zaniness was played out. I normally don't like the fact that sitcoms put a lot of clear punchlines in the script but the characters don't realize they're being funny. For whatever reason, it works in Arrested Development, especially since the few times they almost break the 4th wall and laugh at themselves, it becomes teh most effective laugh track ever. Just like my top dramas, my top comedies set a specific tone and point of view basically 20 seconds into any given episode, and Arrested Development is no difference at all. It is the greatest modern comedy, to which all should be compared.
1.) Seinfeld
At the end of the day, Seinfield keeping up that insane level of quality, consistency over 22-24 episodes a year, for nine years, is just too overwhelming to pass up. Combined that with the show's insane legacy, insane reach, insane level of influence across the next few decades of comedic television, it is rightfully revered. But you know why it keeps its spot at #1, and probably will always have it is because it is also so damn funny. Yeah, at the end of the day, how much a comedy show makes you laugh is ultimatley the #1 criteria. There are others, but lose me with shows that are so pointed, or so of its time, but aren't at the end of the day all that funny - the Fleabags, and Community's of the world. Seinfled isn't any of that. It is a comedy show. The actors know it is. They were given the funniest of material by Larry David, Jerry Seinfeld, and the other writers, for nine seasons and delivered episode after episode.
I say that I think the peak of Arrested Development is higher, but in all honesty even that may not be true. If we look at Seinfield's say third through fifth season, it is right up there. Just take this stretch of 15 episodes in its 3rd season - starting with The Library (5th episode), ending with The Limo (19th) - in that stretch you have The Parking Garage, The Tape, The Nose Job, The Stranded, The Red Dot, Teh Subway, The Pez Dispenser, and The Boyfriend. Hell, the three or so episodes I skipped that stretch are all world beaters in their own right. No show perfected the 22-minute sitcom format better than this one - inventing a whole style of having 3-4 interconnected storylines that somehow always coalesced in the final segment. It seems quaint now with how wide the format has been stretched, but the underlying ethos of Seinfield is still unparalleled.
Seinfeld gets some criticism for becoming a bit broader once Larry David left - if anything that is an overstatement, but it did become slightly more plot driven. It was never a show about nothing, but it was closer to that than in the years after Larry left. That said, the show was still just as funny, just as zany, and even if the plots got more contrived - well lucky for them the characters were already cartoons in teh best way in George, Kramer and Elaine. In the end it is that - you have the best female character ever (other than maybe Lucille Bluth), the best phyiscal comedy character ever, and maybe the single funniest character ever period. That was so good, even Jerry's clearly average at best acting chops couldn't really dent it. Seinfeld was the best show when it was on. And it remains the best show all these years later. Likely nothing in my lifetime of ingesting TV will really unseat it.
