The 10 Funniest HBO Sitcoms

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The 10 Funniest HBO Sitcoms

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.

10. Insecure

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.

9. Enlightened

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.

8. Girls

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.

7. Silicon Valley

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.

6. Eastbound & Down/Vice Principals

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.

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