HBO has had a serious drama problem of late. The network attributed with kick-starting the “Golden Age of Television” currently only programs four scripted dramas. Game of Thrones and The Leftovers remain excellent but are heading in to their final (or final-ish) seasons. True Detective started out as strong as any show in recent memory before capsizing with a disastrous second season, while Westworld turned into annoying fan-theory fodder right after Vinyl imploded so spectacularly it became more compelling offscreen. To say nothing of the imminent, super silly-looking Young Pope.
Comedy-wise, HBO has never had this problem. After such broad early sitcoms as 1st & Ten and Dream On, both of which reviled in the looser standards of pay cable, HBO kicked off its prestige era with The Larry Sanders Show in 1992—or with Robert Altman’s Tanner ‘88 miniseries, if you’re a purist—and has never looked back. Today, HBO is absolutely glutted with excellent comedy shows; with Pete Holmes and Judd Apatow’s Crashing, Bill Hader’s Barry, and the Duplass Brothers’ Room 104 premiering in the next year, we can assume the network will continue to attract top-tier comedy artists for years to come. So, today we’re looking back at the best HBO comedies of the past twenty-four years. Or twenty-eight, if you want to be a dick about it.
To help narrow things down, we’ve decided to exclude shows that initially premiered on other networks, even if they were then ported to HBO. Unfortunately, yes, that excludes excellent series like Extras, The Kids in the Hall, Da Ali G Show, Summer Heights High, or even the extremely weird animated podcast adaptation The Ricky Gervais Show. Consider those to be honorable mentions.
If Issa Rae’s Insecure continues at its current parabolic rate, I have no doubt it will soon earn a higher placement on this list. Not that this show cares about anyone’s approval; that’s one of the great things about it. Insecure muscled its way through HBO’s lilywhite line up, telling the stories it wanted to tell, and saying what it wanted to say about the lives of young black professionals, anchored by Rae’s star-making performance. Just look at the scene where Rae wins over the crowd at an open mic night with her song “Broken Pussy.” Even as Insecure’s characters stumble over their own anxieties, they sometimes stumble into moments of clarity and success, just as Rae does—strutting in and out of her light, gleefully rapping about pussy.
When HBO cancelled Enlightened after its masterful second season, it felt like a punch in the heart as well as the gut. TV was so obsessed with bad men doing shitty things that seeing a woman (Laura Dern’s Amy Jellicoe) trying her absolute hardest to do the right thing was a massive breath in fresh air. Series creator and low-key genius Mike White crafted one of the most satisfying “punch up” storylines of all time, as Amy tried to expose the evil corporation that demoted her while simultaneously struggling to become an “agent of change” for her friends and family. White also drew on his own experiences to create a uniquely nuanced depiction of mental health and addiction, at a time before that sort of endeavor in vogue. Enlightened was happy to take the low-ratings bullet in order to pave the way for others to do the same.
I’m gonna fight for this one. There are three kinds of people in the world: those who find both Lena Dunham and Girls irritating and unwatchable, those who love Girls but hate Lena Dunham, and those who simply think she’s great and her show is the best. I fall into that—very small—third group. Sure, the assembled Brooklynites hit regular and unforgiving ethical lows, and the show itself paints such a bleak portrait of post-collegiate life for young New Yorkers that you’d be forgiven for classifying it as a drama. But what we often forget is that this show is goddamn funny. Dunham established Hannah Horvath’s persona right up top—“I think I may be the voice of my generation. Or at least a voice. Of a generation.”—and has followed through over five seasons with an endless supply of thoughtfully observed, compellingly human moments. True enough in their articulation that, while they might not be “ha-ha” funny, they still hit the same gooey part of our brains. Even the show’s most depressing episode, the fifth season’s “The Panic in Central Park,” immediately provided us with a deadly earnest Desi asking a petulant Marnie, “you know you just recoiled from my touch?” Anyway, I think this show is the American equivalent of Chekhov. Fight me in real life.
We knew going into Silicon Valley that it had a dream cast of young, nerdy comedians and was helmed by Mike Judge, whose forte happens to be satirical workplace comedy. Still, past accomplishment is no indicator of future success, and there was still room for this to go off the tracks. We did not foresee the Silicon boys becoming the sharpest, funniest and most self-destructive comedy ensemble in recent memory. A true example of a fully serialized sitcom, Silicon Valley almost mirrors Game of Thrones in it its “I am utterly riveted in anticipation of how this latest plan will fall apart” factor. Sure, as we head into the fourth season, we’ve begun to recognize some of the more frequent rhythms at play. But as far as I’m concerned, this ensemble can sustain the “one step forward, two steps back, four unexpected steps forward” model as long as it wants.
I can pinpoint the exact moment I turned into a massive Danny McBride fan, having previously been confused and annoyed by his presence in Pineapple Express. (I was in the wrong, I know). Early in the first season, Kenny Powers downs a beer in his car while listening to his own audiobook. As he puts in a new cassette of his boastful, foul-mouthed ramblings, a calm male audiobook voice intones “You’re listening to You’re Fucking Out, I’m Fucking In, by Kenny Powers.” All was forgiven. Initially conceived as a movie that became too good at four hours to cut down to two, Eastbound & Down turned the story of a washed up ex-major league pitcher obsessively striving for relevancy into a comeback story of epic proportions. Kenny would undergo an absurd odyssey on his path back to fame, but series creators McBride, Jody Hill, and Ben. T Best would never sacrifice their honest portrait of a man eaten alive by his own ego for the sake of a joke (except, of course in that insane episode with Will Ferrell, a Civil War plantation, and a cannon). The same team reunited earlier this year for the tonally similar Vice Principals, again capitalizing on McBride’s magnetic, spontaneous onscreen presence, and adding in a killer repartee with Walton Goggins.
Even though he had dominated British comedy for more than two decades, no one was waiting with baited breath for Armando Iannucci’s hot take on American politics—not until the cult phenomenon of his 2009 opus In the Loop, that is. His subsequent leap to HBO delivered on every one of the film’s promises—bizarre construction, foul-mouthed put-downs—and then some. Julia Louis-Dreyfus permanently destroys any notion of a Seinfeld curse from the pilot, leading the charge as the vain and incompetent VPOTUS Selina Meyer. Granted, the idea of a bumbling cabinet of weak-willed assholes isn’t quite as funny as it used to be. But even with the Rogue Gallery that is our incoming administration, I’m confident this team easily outpace even their vulgar, capricious idiocy.
By the mid-90s, SNL had become an overcrowded, choppy mess. The most innovative, exciting developments in sketch comedy were happening elsewhere, and Mr. Show with Bob and David immediately joined the ranks of the new greats like The Kids in the Hall and The State. But Mr. Show had even loftier ambitions. Its central gimmick—that the end of every sketch is the beginning of the next—sometimes made for smooth transitions and sometimes not, but it always gave us the sense that we were fully immersed in a sketch universe with rules of its own. Even the odd sketch that didn’t work still operated with rare fearlessness, and when the show was on its game—as with “Young People and Companions” or “Larry Kleist: Rapist”—it reached highs that have never been surpassed. Plus, it was also the central congregating place for all of early 90s alt-comedy, producing a graduating class which now dominates the current comedy scene in every way imaginable.
When I was a kid, there was a shelf high up in the phone cabinet, off the kitchen, where my parents kept special DVDs. No, not like that. I mean HBO TV shows that swore too much to be down with the Harry Potters where any of us meddling kids could get at them. When I was finally allowed to stay up late with my parents and uncle to watch these shows, the first one they showed me was an early season of Curb Your Enthusiasm.
Larry David may have invented a certain kind of clockwork comedic universe for Seinfeld, but he perfected it in Curb, a show whose very name is synonymous with the cumulative, crushing dramatic irony that usually precedes its instantly recognizable theme song. David, playing the worst possible version of himself, may make a million and a half petty decisions in each episode, but not a single one will be ignored in the cosmic retribution awaiting him at its end. David would go on to diversify this approach in later (and more infrequent) seasons, but Curb remains his calling card and finest achievement, still the gold standard against which HBO comedies are judged.
Had we ever seen anything quite like Flight of the Conchords before it? Have we seen anything quite like it since? Usually shows that feature lovable losers back off on their loserdom at some point; even Jerry and George manage to sell a TV show. Not so with Flight of the Conchords, which never passed up an opportunity to remind us that its main characters had nothing going for them and never would. But that that was fully beside the point. Bret and Jemaine were the kind of perfectly balanced comedy duo we hadn’t seen since Laurel and Hardy, and they joined a cast rounded out by star-making performances from Rhys Darby and Kristin Schaal. The second season may have featured less of the Conchords’ greatest hits, but the overall writing took a massive step up—think of Murray’s four-episode arc with the Prime Minister of New Zealand, or the episode where the duo’s fortunes collapse after Jermaine buys a new teacup. In two brief seasons which constantly strove to refine themselves, we were treated to the most depressing version of New York that we still desperately wanted to live in.
We lost Garry Shandling in March, a low point in a year full of beloved celebrities’ deaths. He was a unique kind of visionary, a comedy guru who largely retreated from fame after Larry Sanders’ perfect finale, preferring to coach and advise up-and-coming writers at regular basketball games in his Los Angeles home. Thank God he left behind The Larry Sanders Show, a scathing indictment of show business’ solipsism and greed. Now that it’s finally streaming on HBO GO, hopefully the uninitiated to go back and recognize its unparalleled influence in television.
The show can be hard to get into. The haircuts, clothes and guest stars are aggressively, aggressively mid-90s, and some episodes fly so low to the ground that you barely notice the nuanced comedic exchanges occurring every second. But, if you hold on to the series’ main entry points—the cavalcade of celebrities ready to play themselves at their worst, the unmatched chemistry between the show’s central trio, Larry (Shandling), his oafish sidekick “Hey Now” Hank Kingsley (Jeffrey Tambor) and his murderously effective producer Artie (Rip Torn)—it will bring you headfirst into a breathlessly hilarious nightmare version of Los Angeles.
Still, the show’s edge was only surpassed by its unlikely heart. There was infinite sadness to the story of Larry Sanders, a man trapped by his own aspirations, who had grown addicted to fame even as he hated every second of it. All he can do is court his studio audience more and more desperately every night. In the end, the song that played over the finale’s credits said it all: “Will You Still Love Me Tomorrow?”