The 10 Funniest HBO Shows of All Time

Comedy Lists
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Earlier today HBO announced that they had poached High Maintenance away from the web, where the show has been an underground hit for the last few years. High Maintenance could be the next great HBO comedy, and joins a nice line-up that includes Veep, Silicon Valley, Girls and upcoming shows starring Dwayne “The Rock” Johnson and Jack Black. HBO has a long history with comedy, with a healthy commitment to stand-up since the 1970s, and a spate of original sitcoms that stretches all the way back to 1st & Ten in 1984. If you grew up in the ‘80s and ‘90s with access to HBO you probably remember shows like the news parody Not Necessarily the News (the original home of the sniglet) and the sex-filled nostalgic sitcom Dream On. HBO’s better-than-TV bonafides actually started with prestige comedy before they became famous for drama, with all-time classics The Larry Sanders Show and Mr. Show debuting in the 1990s. Drama quickly lapped comedy once The Sopranos and The Wire came around, but HBO has continued to produce such great comedies as Bored to Death, Flight of the Conchords, Enlightened, Getting On and Family Tree. Only ten shows could make our list, though, and many of our favorites couldn’t make the cut. To make it easier we decided to focus exclusively on sit-coms and talk shows, leaving stand-up specials and the One Night Stand stand-up anthology out of consideration. As always, feel free to let us know what we got wrong in the comments below, or on Twitter @Paste_Comedy.

10. Da Ali G Show

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Da Ali G Show debuted in the UK, the home country of star Sacha Baron Cohen, but its second two seasons were made for HBO. As Ali G, a clueless hip-hop loving Brit, Baron Cohen brilliantly satirized both political and entertainment journalism, taunting people like Newt Gingrich and Ralph Nader with vacuous and absurd questions. His best work might have come with Borat, though, where he exposed modern-day racism and xenophobia through pranks and his offensively cartoonish Kazakh caricature. Da Ali G Show was smart, vulgar and hilarious.

9. Veep

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Initially I thought Veep was too new of a show to consider, and then I realized it was already on its fourth season. Armando Iannucci’s pitch black satire of Washington politics is as cynical as it is hilarious, and a great American counterpart to his classic British show The Thick of It. It also has one of the best casts of any comedy on TV today—every cast member is pretty much perfect. If you want to read more about Veep, check out our list of five reasons why you should be watching it.

8. The Chris Rock Show

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The Chris Rock Show capably translated Rock’s stand-up persona to the talk show format, skewering American race relations and the battle of the sexes in various skits and pre-taped segments wrapped around celebrity interviews and musical performances. Rock was a surprisingly good interviewer, though, using the freedom of pay cable to go deep and discuss potentially controversial topics with his guests. HBO has a long history of comedy shows about current affairs, from Dennis Miller Live to Real Time with Bill Maher; until John Oliver came around, Chris Rock hosted the best of the bunch.

7. Last Week Tonight with John Oliver

This should keep moving up the list with time. John Oliver has lapped all the other news satire shows by focusing on global issues and devoting up to half of each episode on a single main story. He effortlessly explains complicated issues in hilarious fashion, helping his American viewers learn crucial information from around the world while still entertaining them. Unlike The Daily Show, where it’s been obvious for years that the circular cynicism of US politics has just crushed Jon Stewart’s will to perform, Oliver still approaches every episode with vigor. Perhaps he too will burn out in time, but hopefully the once-a-week schedule and periodic season breaks keep him fresh. John Oliver is the most important comedian currently working in the worlds of public affairs and current events, and it’s hard to imagine him having the same freedom anywhere else that he has on HBO.

6. Sex and the City

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Sex and the City had the biggest cultural impact of any of these shows, and indeed, perhaps of any HBO show. It’s one of the most scrutinized and written about shows of all time, and yet it’s still easy to forget how funny the show could be. As a smart look at women’s lives at the turn of the century, its influence can’t be denied. As a venue for Kim Cattrall to deliver withering one-liners and to tackle sexual and romantic issues that had never been broached by TV before, the show’s value can’t be overstated.

5. Eastbound & Down

I feel like a lot of people dismiss Eastbound & Down as vulgar shock comedy, a TV version of the fratty comedies that proliferated over a decade ago after the success of the Farrelly brothers and American Pie. Jody Hill and Danny McBride’s vision is far deeper and pointed than that, though, parodying not just sports or Southern culture but the type of unhealthy masculinity that underpins so much of American culture. It has more in common with the best work of Adam McKay and Will Ferrell, but it’s darker and edgier than Stepbrothers or Talladega Nights, more violent and more truthful. It’s one of the few comedies I can think of where I was often afraid of what was about to happen, like I was watching a horror film or thriller. The first season in particular was a modern masterpiece, but the show remained on point throughout its four seasons.

4. The Kids in the Hall

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HBO was the exclusive American home of the first (and best) few seasons of The Kids in the Hall, which remains one of the five best sketch comedy shows of all time almost 30 years after it debuted. Throughout its run Kids in the Hall was surreal and intelligent, rarely resorting to cheap cynicism and remaining unfailingly polite in a way that evoked their Canadian origins. The five regulars were all talented writers and performers, and together they created a show with a very broad and diverse point of view that somehow still felt like a unified entity. It was also perhaps the most gay-friendly show on TV when it debuted—Scott Thompson lent the show a transgressive edge at a time when TV would acknowledge homosexuality but never let homosexual characters express their love in any kind of physical way.

3. Curb Your Enthusiasm

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Larry David pulled off the rare successful second act in television comedy—Curb Your Enthusiasm was almost as hilarious as Seinfeld, and thanks to HBO’s more laidback production schedules, it actually lasted longer than his first sitcom, running off and on from 2000 to 2011. (It’s still not officially cancelled, although David apparently is doubtful that it’ll return.) Curb was Seinfeldian in its rhythms, with David basically playing the George Costanza version of himself as an eternally perturbed and self-defeating schlemiel who just happens to be fantastically wealthy after creating a show called Seinfeld. A lot of cringe comedy forgets to actually be funny, but that was never a problem for Curb, which remained as funny (and cringeworthy) as ever over its eight seasons. And it’s not just the increasingly uncomfortable situations or David’s masterful escalation from annoyance to rage to embarrassment that made the show work so well—David surrounded himself with a fantastic cast, from regulars like Cheryl Hines, Jeff Garlin, JB Smoove and Susie Essman, to such recurring guest stars as Wanda Sykes, Richard Lewis, Ted Danson, Mary Steenburgen and Bob “’Super Dave’ Osborne” Einstein. Oh, and also there’s an entire season about a Seinfeld reunion, guest starring the original cast. Curb can be hard to watch at times, but it was always hilarious, and was HBO’s trademark comedy throughout the last decade.

2. Mr. Show with Bob and David

Before alternative comedy was a recognized thing, there was Mr. Show with Bob and David, a genius sketch comedy show that had a criminally short run on HBO from 1995 to 1998. Each episode was loosely based around a central theme and laboriously structured, with sketches leading directly into each other, and sometimes even wrapping around each other like Russian nesting dolls of comedy. Although celebrated for its absurd point of view, Mr. Show didn’t shy away from the real world, often tearing into the inequalities of society and the increasing domination of corporate America. Not every bit landed, but the show still had a shockingly high batting average over its four seasons, and very little of it feels dated today. The show isn’t available on any of the major streaming sites, including HBO Go, but the DVDs are still cheap on Amazon, and much of the show can be found on YouTube. If you’re wondering why the recent news of a reunion is such a big deal, check out the original Mr. Show and you’ll find the answer.

1. The Larry Sanders Show

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It’s not an indictment of HBO’s comedy development that their two best comedies went off the air 17 years ago. They’ve had lots of great comedies since then. It’s just a testament to how great and important Mr. Show and The Larry Sanders Show were. Before HBO established itself as a dramatic powerhouse with The Sopranos and Oz, Larry Sanders was their flagship scripted program. It was literally a decade before its time, prefiguring shows like The Office and Arrested Development with its lack of a laugh track, a single camera setup and a roster of unlikable characters. It blurred the line between reality and TV show, with real-life actors playing themselves on the talk show within the show, and often sending up their public personas. It also featured three unforgettable performances from Garry Shandling, Jeffrey Tambor and Rip Torn, who were all as good at playing the desperation and futility of their characters as they were the comedic moments. Despite its inside showbiz setup and caustic humor, its characters were fully-formed, believable people. It was a very smart and human show. Unfortunately it’s not currently available on HBO Go or Netflix, but select episodes can be watched through Crackle or through Hulu’s website.

Garrett Martin edits Paste’s games and comedy sections. Sometimes people follow him on Twitter @grmartin and he’s never figured out why.