While it’s in danger of being overshadowed in the age of streaming, HBO has been the home to some of the greatest TV comedies ever made. Long before Netflix removed all the boundaries of TV production, HBO removed most of them. The premium cable network that marketed itself as “not TV” allowed for creative freedom, experimentations with the form, and uncensored adult content.
Larry David’s show Curb Your Enthusiasm revolutionized the single-camera comedy, Veep brought the incisive political satire of The Thick of It stateside, and Barry has found the unlikely connective tissue between improv and contract killing. HBO’s comedies have given fans a ton of iconic characters over the years.
Gene Cousineau (Barry)
While Bill Hader has been giving a stellar lead performance in Barry, the show’s funniest character is the eponymous ex-hitman’s acting coach, Gene Cousineau, played hysterically by Henry Winkler.
Throughout the series, Gene has acted as a kind of father figure to Barry, even though he’s frequently shown himself to be self-centered and sort of a jerk.
Jared Dunn (Silicon Valley)
There are plenty of hilarious characters on the Pied Piper team in Silicon Valley, from the socially awkward CEO Richard to the oft-bullied programmer Dinesh to the Satan-worshipping Gilfoyle. But arguably the show’s funniest character is Jared Dunn, who left Hooli to join Pied Piper.
Zach Woods plays him as quintessentially bland and mild-mannered, which juxtaposes brilliantly with his surprising prowess on the dating scene. “This guy f**ks!”
Murray Hewitt (Flight of the Conchords)
Played by the masterfully deadpan Rhys Darby, Murray Hewitt is the dim-witted manager of Flight of the Conchords. His day job is deputy cultural attaché in New York City’s New Zealand consulate, and he’s much better at that than managing the band.
Murray is really passionate about the band and getting them gigs, despite the fact that he’s almost entirely incompetent at the basic requirements of the job.
Amy Jellicoe (Enlightened)
One of the most underrated shows in HBO’s history is the half-hour dramedy Enlightened, which starred Laura Dern as Amy Jellicoe, an ambitious office highflier who has a nervous breakdown at work and returns to the company after rehabilitation, albeit with a much lower position on the corporate ladder.
As always, Dern gave a fantastic performance in Enlightened. It’s just a shame that not a lot of viewers tuned in, so it only lasted for two seasons.
Leon Black (Curb Your Enthusiasm)
In the sixth season of Curb Your Enthusiasm, Larry David took in a family that lost their home in the hurricane. He also took in their brother, Leon, who was already living in L.A. and stayed in Larry’s house long after the rest of his family left. He has since become Larry’s streetwise sidekick.
J.B. Smoove’s fast-paced ad-libs made him a perfect fit for the improvised world of Curb, while his on-screen chemistry with the real David is off the charts. He was a late addition to Curb, but now it’s impossible to imagine the show without him.
Borat Sagdiyev (Da Ali G Show)
Sacha Baron Cohen’s now-iconic on-camera pranks, feared by public figures across the world who could be lured into a trap by one of the comic’s beloved creations, originated on HBO’s airwaves on Da Ali G Show.
While Ali G, Borat, and Brüno are all fantastic characters who have brought out the hidden prejudices of interviewees, the funniest of them all is undoubtedly the Kazakhstani reporter.
Larry Sanders (The Larry Sanders Show)
Garry Shandling was responsible for one of the most spot-on satires of late-night television with his lead performance in The Larry Sanders Show opposite Jeffrey Tambor and Rip Torn.
Larry’s clashes with his co-workers and the celebrity guests on his show always raised a few chuckles, while the series itself brought meta-ness into the mainstream.
Kenny Powers (Eastbound and Down)
Danny McBride had made a name for himself playing supporting roles in Apatow comedies when he was given the chance to develop his own half-hour show for HBO. Eastbound and Down focuses on Kenny Powers, a disgraced Major League pitcher who returns to his hometown to teach gym.
As he claws his way back into professional baseball, Kenny gets into increasingly outrageous antics. The absurd lengths he’ll go to for a scheme are unceasingly hilarious.
Selina Meyer (Veep)
Julia Louis-Dreyfus broke the so-called “Seinfeld curse” that supposedly prevented any of the seminal sitcom’s cast members from starring in another successful series when she took the lead role in HBO’s political satire Veep.
Selina Meyer begins the series in the office of Vice President, but she later becomes the President and, after that, leaves her political career behind. She was never anything less than hysterically funny throughout the show’s entire run.
Larry David (Curb Your Enthusiasm)
Larry David left Seinfeld after its seventh season and returned to the standup stage, which eventually led to a special on HBO that was intercut with improvised scenes from David’s life. This led to the conception of a half-hour series revolving around David’s fictionalized self.
The TV version of Larry has become a mouthpiece for what people think in everyday situations, but don’t say due to the restrictions of social convention. He has a term for everything: “stop and chat,” “chat and cut,” “medium talk,” “outfit tracker” — the list goes on.