Garry Shandling may be best known for The Larry Sanders Show, his landmark comedy about the world of late night talk shows. It was his second TV series, after the meta, fourth wall-breaking It’s Garry Shandling’s Show. Shandling was also a successful standup comic, guest host of The Tonight Show, and actor. To a younger generation, he was Senator Stern in Iron Man 2 and Captain America: The Winter Soldier.

Judd Apatow got his start on The Larry Sanders Show. Shandling picked him up from the short-lived The Ben Stiller Show, giving Apatow his first chance to direct television. After preparing Shandling’s memorial service following his death, Apatow decided to make a documentary about his mentor. The Zen Diaries of Garry Shandling is a two-part HBO film covering Shandling’s life and career. Shandling kept personal diaries, which appear in the film.

Apatow spoke with /Film by phone this week and our conversation begins with Garry Shandling and branches outward, eventually touching on Apatow’s outspoken support of the #MeToo movement and his condemnation of Hollywood abusers. The Zen Diaries of Garry Shandling premieres Monday, March 26 on HBO.

Garry passed away rather suddenly. Had you begun a documentary while he was still alive?

No. I started working on it after his memorial. I cut some short documentary pieces for the memorial and when I was working on it, I thought that there clearly was enough material to make a long form documentary. I spent about a year looking at material and searching for material and just under a year editing the documentary.

I think I got the answer from Zen Diaries, but I always wondered, why wasn’t It’s Garry Shandling’s Show as revered as The Larry Sanders Show?

I think it’s because Garry found a way to end The Larry Sanders Show which gave it the feeling of a completed thought, that the entire series was almost like one story. So I think the fact that he won the Emmy for writing for the finale with Peter Tolan and that there was a lot of fanfare at the end of the show gave it a little more prestige, but It’s Garry Shandling’s Show is equally as influential. A lot of the staff from the show went on to create and run The Simpsons. In the documentary, they talk about how Garry’s DNA really was in The Simpsons. At a time when TV wasn’t that imaginative, It’s Garry Shandling’s Show really broke down a lot of walls. I think he showed people what was possible if you just opened up your mind a little bit more.

It blew my mind when I saw it, and I can see from Zen Diaries that Larry Sanders became more personal for him and he had more control over it, so maybe it overshadowed It’s Garry Shandling’s Show.

Yeah, and I think a lot of it also has to do with how accessible seeing the shows is. Which ones are available to watch? Are they on DVD? Are they streaming? That tends to change.

What was his obsession with his hair?

A very good question. I never asked him directly how he felt about his hair. I think his hair was a metaphor for his concern about how he looks generally. It all turned into “How’s my hair?” but it really was, “How am I looking?”

My sister met him once and told him his hair looked great. He turned around and said, “Will you marry me?” 

[Laughs] That’s hysterical. Garry later said, “It doesn’t matter how you look. It’s the hair on the inside that matters.”

Larry Sanders makes sense as the halfway point to end part one, but did that throw off your timing since part two covers a lot more material?

No, I tried to think of a logical place to end the first part. I think that The Larry Sanders Show was the beginning of another era for Garry. When I started the project, I didn’t know how long it would be. I thought maybe I could fit it in in about two hours. Then it became clear that without time limitation, you really could explore the depths of Garry and that he deserved the treatment that was closer to what people like Bob Dylan, Elvis and Frank Sinatra get. So I called Richard Plepler at HBO. He loves Garry so much. He said, “Whatever the best way to tell this story is, that’s what you should do.” I was very lucky to have that kind of support.

Was culling all of this Garry footage at all like your comedies where you have long takes of improvisation and decide which pieces to use?

I just had to look at it the same way I would look at a film which is it’s the story and there are certain movements. What footage do I have available to me to get a certain time and certain ideas across? So much of making a documentary is about what is the best way to explain a moment or a feeling. Luckily, Garry had done a bunch of podcasts in the last few years of his life, with people like Pete Holmes, Marc Maron and Pauly Shore. They really grilled him about his life and his choices. He also did a very long interview for the Television Academy, a three hour interview. Those were very helpful in guiding me as to how to lay this out.

I always liked What Planet Are You From? and I never knew it had such behind the scenes troubles for him, but the behind the scenes weren’t why the movie wasn’t a success, were they?

That was a very difficult situation for Garry because he worked hard on the script. It was -something he was very passionate about. Mike Nichols came on as the director and for whatever reason, they were not a good pair of collaborators. Mike Nichols lost faith in the project very early and seemed to mail it in the rest of the way. Garry was frustrated. He wanted to work long hours and grind the scenes and do a lot of takes. Mike Nichols was doing very few takes and wrapping for the day 4:30. Garry really didn’t know how to navigate that relationship. It certainly resulted in a movie that wasn’t what Garry hoped it would be.

Had he had a different director on that film, someone maybe more like yourself, do you think Garry might have done more movies?

I do think the fact that he had a bad experience broke his spirit a little bit. He was very excited about it and when it went so badly, it led to him never writing a movie again. He talked in the documentary about how he was so surprised by the toxicity of that relationship that it made him feel like he didn’t know who he could trust. I think that is a sad part of Garry’s story. He was such a brilliant writer and it seemed to drain him of his belief that he could succeed in that arena.

At what point did you start reading all of the diaries?

I started reading them when I was working on his memorial service. I put a book together to give out to the people who attended, scanned some pages which had funny or inspirational writings on them. And then when we decided to make the documentary, I got permission from his estate to read everything. He had been working on a few projects which would have used the diaries. He had shot some test footage for a documentary or potentially a series which would use his diaries as a jumping off point. He also wrote in the diaries that he was considering putting out a book of the diaries. So I took that as a kind of permission to explore those ideas and I tried to be as sensitive as possible about what to use. But, it does give you a window into his mind that he was a person that was private and didn’t share what he was thinking with an enormous amount of people. It allows the documentary to be as personal as documentaries can get.

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