Artie (Rip Torn), Larry (Garry Shandling) and Hank (Jeffrey Tambor) Photo: HBO

The 1990s were a golden age for comedy. Over here we had The Day Today, Alan Partridge, but also choice American imports. I don’t mean Friends, a show that has never made me so much as crack a smile, but the shows that nestled bizarrely in the post-Newsnight slot on a Tuesday night. At 11.15pm came Seinfeld. But that was merely a warm-up for the main attraction: The Larry Sanders Show, for my money still the best sitcom ever made.

HBO has just released a two-part documentary by filmmaker Judd Apatow, entitled The Zen Diaries of Garry Shandling. Apatow got his big break with the creator and star of Larry Sanders and kept in close contact until he died in 2016 aged 66. Part one delves into the comedian’s hard upbringing—his brother died from cystic fibrosis when Garry was 10 years old; his mother never recovered mentally—and his 1980s hit, It’s Garry Shandling’s Show, a self-reflexive comedy about a stand-up. Part two is about how he came to create his best work, and what it cost both him and those around him.

The “Zen” in the title refers to Shandling’s interest in Buddhism, and the self-improvement diaries he wrote to keep darkness at bay. That same darkness motored his humour. The Larry Sanders Show takes on the monstrous ego of the late-night talk-show host, his Hollywood guests and the team around him, damaged by having to attend to his every whim. “Does my ass look big in these pants?” is Larry’s refrain to his producer Artie (exquisitely played by Rip Torn.) Artie must always cheerfully insist that no, of course, his ass looks perfect.

As the documentary shows, Shandling took immense pains to get every joke burnished and every scene perfectly plotted. The stakes were high. In the early 1990s, NBC offered him $5m to take over David Letterman’s late-night slot. But he turned it down for a show about a talk show. He was vindicated: the show ran from 1992-1998, 90 episodes, with multiple Emmy wins.

For all the bitching and kvetching, The Larry Sanders Show tries to “tell the story of human beings.” As well as Artie there’s Larry’s sidekick Hank (Jefferey Tambor), a roiling mass of resentments masked with a false on-screen jollity; deadpan guest booker Paula (Janeane Garofalo); his canny assistant Beverly (Penny Johnson). Each one is given their own inner life—all the funnier for being so messed up.

“Artie must always cheerfully insist that no, of course, Larry’s ass looks perfect”

There’s plenty of delicious showbiz satire too. When Ricky Gervais (who owes much to Shandling) took the idea of celebrities playing themselves for Extras, he made them too caricatured to be truly cutting. But here they are close to what you imagine is the real thing. When Sharon Stone starts dating Larry, she toys with him mercilessly. Helen Hunt plays herself as incredibly boring. David Duchovny develops a weird obsession with the host, much to Larry’s discomfort.

But the most merciless portrayal is of Shandling himself. As Apatow reveals, Garry was just as difficult as Larry. When he broke up with Linda Doucett, who played Hank’s assistant the ever-sunny Darlene, he also sacked her. She successfully sued him but here recounts tearfully how she still loved him. He fell out with his manager and sued him for $100m. Although he won, that conflict deformed the final season of the show as Shandling took his revenge through an agent character who might as well be the spawn of Satan. Nothing private was off-limits: when Doucett posed for Playboy, they had her character do the same—close to the bone humour, and all the funnier for it.

The grammar of the show’s comedy was more complex than most 22-minute sitcoms. It took the easy-listening humour of the host’s opening monologue—all those Clinton and cigar jokes—and made that the material from which sharper humour could be mined (with no audience laughter.) Why is this monologue or sketch duff? Turns out one of the writers is sleeping with the intern. Or Hank is insisting on his own (unfunny) line because he’s angry with Larry. The interview chit-chat sets up the jokes in the advert break. In one episode, Robin Williams shifts from manic hilarity to pained self-doubt—“Cut the bullshit how am I doing?… Shall I continue with my kid’s penis?”

Ironically given the show centres on Larry, the one episode in which he barely appears is its crowning glory. He’s sick and there are no guest hosts available—so Hank gets his night in the sun. “What if I suck?” he asks Artie, finally showing some winning self-doubt. But he triumphs—only to crash and burn when his ego inevitably reasserts itself.

That’s the key to Larry Sanders. In the opening credits, Hank tells the studio audience: “The better you are, the better Larry is.” I’d always taken this to indicate Larry’s all-consuming selfishness: even the audience’s laughter is co-opted for his own ends. But after watching this documentary, you could read it another way. Shandling genuinely struggled to be a better person. He mentored other comedians—not only Apatow, but Sasha Baron-Cohen and Sarah Silverman, who both offer their gratitude here. It’s a glimpse of a kinder world outside the hothouse of making a television programme.

We’d all like to get to that place: Shandling certainly did. The Larry Sanders Show is his whip-smart and very funny account of his journey towards turning off the television, finally, as he says in the last ever episode, feeling free to flip.

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