Judd Apatow says Garry Shandling was 'obsessed with the truth' — and his new HBO documentary tells all

Ken Tucker
Critic-at-Large, Yahoo Entertainment
Garry Shandling and Judd Apatow. (Photo: Larry Watson/HBO)

One of the greatest documentaries ever made about the life of a comedian, The Zen Diaries of Garry Shandling premieres Monday on HBO. It’s an extremely funny, extremely moving, extremely warts-and-all look at the comic actor, who died in 2016. It’s created by director-writer Judd Apatow (The 40-Year-Old Virgin, Knocked Up), who was a friend of Shandling’s as well as a former employee — Apatow worked on Shandling’s immortal HBO sitcom The Larry Sanders Show, the ultimate talk-show satire. Apatow made the documentary in part to help secure Shandling’s legacy: “I think there is so much new content in this culture that it’s hard for young people to go back and explore all of the great shows of the past. There’s, like, 400 new half-hour shows a year, so you have to be a real comedy scientist to start hunting down The Larry Sanders Show or The Odd Couple or The Associates. So I thought this was a great opportunity to educate people,” Apatow says. “The documentary is built to explain who he is, so if you’ve never seen any of the work, it all gets laid out for you.”

Apatow truly does lay out his subject’s life. In the documentary, we are shown pages from Shandling’s diaries. There are perfectly chosen clips of him in performance, as well as wonderful interviews with Shandling friends as various as Jim Carrey, Tom Petty, Bob Saget, Conan O’Brien, Jerry Seinfeld, and Sarah Silverman. The beauty of this four-hour film — shown in two parts — is the way it showcases Shandling’s style, achievements, and troubles in an endlessly entertaining way. Beginning his career as a scriptwriter for sitcoms such as Welcome Back, Kotter and Sanford and Son, and as a standup, Shandling honed an unmistakable voice — it was the sound of the sarcastic whiner, the self-puncturing romantic, and, near the end, the wistful wise man.

“Garry was obsessed with the truth,” says Apatow. “So for every aspect of the documentary, I thought, ‘Garry would want us to play it straight. He wouldn’t want us to turn him into some sort of a saint.’ He was a man who was very kind to a lot of people, but he also had his flaws and insensitivities. He made small and large mistakes.”

Zen Diaries rightly places The Larry Sanders Show (1992-98) as the centerpiece of Shandling’s career — his greatest achievement. But among the “small and large mistakes” that Apatow references are Shandling’s 2000 movie bomb What Planet Are You From? (his brutal treatment by director Mike Nichols will send a shiver down your spine) and, in his personal life, Shandling’s romance with a Sanders co-star, Linda Doucett. When the relationship soured, he fired her — a gross misuse of professional power. “That’s something we all know is wrong and unfair,” Apatow says. “She went on to file a lawsuit. He settled with her and they were friends to the very end. But it took her standing up to him and saying that was wrong.” (Doucett appears in Zen Diaries, speaking of Shandling affectionately.)

Apatow frames the documentary around the central agony of Shandling’s life — the death of his brother, Barry, when Garry was 10 years old. He felt a painful grief that never healed, but which led him into a spiritual life that included Zen Buddhism. “Even when he was learning to be a standup comedian, he applied those principles,” Apatow says. “It was all about trying to be in-the-moment, letting go, trusting himself. It was a real Zen in the Art of Archery approach to being a standup comedian.”

One of the most interesting sections of Zen Diaries is about Shandling filming the DVD extras for the 2007 release Not Just The Best of The Larry Sanders Show. This project — a throwaway bonus item for any performer less of a perfectionist than Shandling — grew to more than eight hours of completely original interviews the comedian conducted with Sanders Show guests such as Seinfeld, Sharon Stone, Petty, Bob Odenkirk, and many others. These interviews proved to be frequently moving, deep-dish discussions — and Apatow sees them as being ahead of their time: “That project in a lot of ways was very influential, because, at a time before podcasting and long-form comedic interviews, Garry was fascinated by the form, and did groundbreaking work. Even Jerry Seinfeld says that one of the inspirations for Comedians in Cars Getting Coffee was his interview with Garry [for the DVD].”

Apatow’s Zen Diaries presents Garry Shandling as the complex man he was, and the man he wanted to become. As Shandling told me when I interviewed him in 1998: “I’m nothing but a man struggling to get better.”

The Zen Diaries of Garry Shandling premieres March 26 and March 27 at 8 p.m. on HBO.

Read more from Yahoo Entertainment: