After Comic Garry Shandling's Death, Judd Apatow Found Zen In His Diaries

Nov 11, 2019
Originally published on November 11, 2019 2:34 pm

Judd Apatow was a teenager when he first "met" comic Garry Shandling in a phone interview for his high school radio show. Years later, their paths intersected again when Shandling, who was hosting the Grammy Awards, hired Apatow to write jokes for him.

Shandling had been Johnny Carson's guest host on The Tonight Show before creating and starring in the groundbreaking comedy series It's Garry Shandling's Show and The Larry Sanders Show. He became Apatow's mentor and close friend.

"He completely changed my life," Apatow says of Shandling. "He hired me to write for his show. He did a cameo on the pilot of The Ben Stiller Show, which I thought was part of why we got picked up. He asked me to direct. ... It was always mysterious to me why he was so kind to me."

Apatow went on to produce Superbad and Girls, and to direct The 40-Year-Old Virgin and Trainwreck, but he always stayed in touch with his mentor. After Shandling's sudden death in 2016, Apatow helped sort through his belongings — including boxes of diaries dating back to 1978.

Shandling practiced Zen meditation for decades, and many pages of his journals are reminders to himself to stay calm, remain unattached to worldly things and let go of his ego.

"I felt like there was so much wisdom in examining Garry's life," Apatow says. "Garry was a wounded person. He was a neurotic man. He was a guy constantly attempting to evolve and heal. I felt like there's so many lessons that people can get from learning about how he lived his life."

Shandling is the subject of Apatow's new book, It's Garry Shandling's Book, which is a companion to the HBO documentary Apatow made last year, The Zen Diaries of Garry Shandling.

"I saw in the journals that he wrote, 'Learn to grow old gracefully. Learn to become a mentor gracefully,'" Apatow says. "Now I'm more tuned into the responsibility of doing that. I'm lucky enough to be in a place where I can help people who deserve to be heard from or who deserve breaks. ... I definitely try to keep that Garry tradition alive."


Interview Highlights

On Shandling's place in comedy

Garry always cut his own path. It always felt like Garry was outside of the system in some way. - Judd Apatow

Garry always cut his own path. It always felt like Garry was outside of the system in some way. So when he did It's Garry Shandling's Show, there really hadn't been a show like that, that was so experimental and weird and which made fun of the whole concept of sitcoms. ...

And then he did The Larry Sanders Show, which was a satire of talk shows. It was a behind-the-scenes look at an anxious, neurotic talk-show host, somewhat like Garry. And in it, he tried to explore the way show business and ego prevents people from connecting and loving each other. That was his premise. And in a way, he was trying to use the show to explore his own psyche. And I always thought he was mocking the part of himself that he didn't like, mocking the person that wanted to be rich and famous and someone who could hold this high position for a long time.

He was a unique, original thinker, and in a way, he was almost like an alternative rock band. And he did all this when TV didn't have much of this. There's a lot of television like that these days, but back in the '80s and early '90s, there wasn't programming like this.

On how Shandling's journals changed his understanding of Shandling

I was surprised that 30 years of journals mainly contained Garry trying to talk to his positive voice. So they weren't journals from the point of view of someone who was just trying to spew all their toxic stuff. A lot of us write in journals like that. We just want to get the bad voice out of our head, and that's not what Garry's journals were like. They were a voice talking to the panicked, anxious voice. So most of the journals were reminders to try to get out of ego, to try to be more kind and loving, to let go. It's 30 years of reminders about the type of person that he wants to be. There were some pages where he was complaining about something, but very few, considering that he did it for 30 years.

On how Shandling's 13-year-old brother died when Shandling was 10, and his parents didn't talk to him about the death or let him go to the funeral

It's hard to know for sure, but it certainly scarred him in a way that affected him throughout his life. I felt that his search for presence was based on the fact that at a moment in his life when he needed to be told the truth, he wasn't told the truth. It's hard to know how accurate all the details are, but what it sounds like was that he was sent away when his brother died, and he was sent to his grandparents, and that they didn't tell him for a little while, but he basically understood what was happening.

And then after his brother died, the family dealt with it by not talking about it, which, I think, for that time period — this is 1960 — is something a lot of people did in post-World War II America. They said, "All right, we're going to move forward, and how we survive this is: We are going to stuff it down deep and not talk about it." And so throughout Garry's life, he was all for being honest and open and vulnerable and present and real — and I think that's because at the key moment of his childhood, people were not real with him.

On how Apatow almost turned down a job as a showrunner for The Larry Sanders Show because he didn't want to ruin his relationship with Shandling

Apatow (right) was the co-showrunner for the final season of The Larry Sanders Show, which Shandling created.
Larry Watson / HBO

I always liken it to trying to paint with Picasso — that if you are painting a painting with him, he probably at some point would turn to you and go, "You're doing it all wrong! What's with the red?" You would always disappoint him, because the show is so in his mind and it's so based on his feelings and experience that when you work on something so personal, how could you ever know what he would do, what's in his heart, how he would behave? ...

It was painful at times. If you pitched Garry a joke and he hated it, you would feel it. It would hurt you, the whole look of disappointment in Garry's eyes. ... There were very few people that Garry felt like could write the show. So when he said, "Hey, can you do me a favor and co-showrun this last season?" I was terrified, because I loved my relationship with Garry and I didn't want something to go terribly wrong with it. I said to him, "Garry, I'll do it. You have to know how hard this is." I was just honest with him in a way that probably no one ever had been. And I was honest about why he was difficult to work with.

On Shandling's perfectionism and growing interest in Zen Buddhism

He just could not just be chill and make it easy on himself. He wanted everything to be amazing. And in his head, the stakes were incredibly high and that is pure ego, and that's why he was always trying to remind himself not to have a big ego. It was a battle that continued, and then at some point near the end of his life, he really did let go and spent a lot more time mentoring people. He basically was satisfied with his work, and people would say, "When's your next show?" And he would say, "Weren't these two enough?" And he did let go.

On how professional success didn't make Shandling happy

He wrote a lot for The Larry Sanders Show about how success doesn't make you happy, and I think for most people that reached certain heights of success or whose dreams come true, they really learn something that a lot of people don't learn: [which] is that most of what happens when you get to that place is you realize that it doesn't work, and in some ways, it's very depressing. ...

I've looked at myself and all of my friends and we've all been in on a very long journey in our attempts to be creative, in our attempts to be successful and to get heard and make things. I've seen all the different ways that people have handled the ups and downs of their careers, and it is a struggle, because you put so much of your self-esteem in having people like you because you're doing a good job.

I think that Garry felt a lot happier in some moments after he stopped trying to do the work. He was very loving and giving, and if you wrote a script or had a cut of a movie, he was always there, 100 percent of the time, to come and give you notes and be so helpful. And I think that was a happier part of show business for him than being up at midnight rewriting a script for his show.

On how Shandling wrote about death in his diaries

He was about to have the surgery that he knew was potentially life-threatening, and in the journals he would say things like, "Death is not a change. Embrace death. It is freedom. Be open, be ready, be joyful to die." That's what it said on all the different pages. It was him trying, in a very Buddhist way, to be comfortable during his exit and to not fight it and to not resist and not see it as something different.

Lauren Krenzel and Joel Wolfram produced and edited this interview for broadcast. Bridget Bentz, Molly Seavy-Nesper and Patrick Jarenwattananon adapted it for the Web.

Copyright 2019 Fresh Air. To see more, visit Fresh Air.

TERRY GROSS, HOST:

This is FRESH AIR. I'm Terry Gross. My guest Judd Apatow has given many actors their first big break or given their careers a big boost through the movies and TV shows that he's produced and-or directed, like "Freaks And Geeks," "The 40-Year-Old Virgin," "Superbad," "Anchorman," "Bridesmaids," "Girls," "Trainwreck," "The Big Sick" and "Crashing." We're going to talk about the comic who gave Apatow his big break and became his mentor and close friend, Garry Shandling.

Apatow has edited a new book built around interviews, as well as the photos, jokes, letters and journals Apatow found in Shandling's home after Shandling's death in 2016. The book is called "It's Garry Shandling's Book," and it's a companion to the HBO documentary Apatow made last year titled "The Zen Diaries Of Garry Shandling." At the heart of the film and book are Shandling's journals, dating back to 1978.

Shandling practiced Zen meditation for decades, and pages and pages of his journals are reminders to himself to remain calm, not get attached to worldly things, let go of his ego - aspirations that came into conflict with his neuroses and his obsessive dedication to his comedy. Shandling became famous as a comic in the '70s, when Johnny Carson was still hosting "The Tonight Show." After making many guest appearances, Shandling became a frequent guest host when Carson was away.

But Shandling's groundbreaking contributions were his two TV shows. "It's Garry Shandling's Show" foreshadowed reality TV and featured a fictionalized version of Shandling that showed him living his life while being followed by a camera crew. The show is very meta, and so is the theme song whose lyrics were about being a theme song.

(SOUNDBITE OF TV SHOW, "IT'S GARRY SHANDLING'S SHOW")

BILL LYNCH: (Singing) This is the theme to Garry's show, the theme to Garry's show. Garry called me up and asked if I would write his theme song. I'm almost halfway finished. How do you like it so far? How do you like the theme to Garry's show?

GROSS: Shandling's next TV series, "The Larry Sanders Show," was also meta. It was a satire in which he starred as the host of a late-night talk show, kind of like "The Tonight Show." Let's start with a clip in which Larry's producer, played by Rip Torn, is asking Larry if he's read the new book about the competition and conflict between late night hosts.

(SOUNDBITE OF TV SHOW, "THE LARRY SANDERS SHOW")

RIP TORN: (As Arthur) What did you think of that book I gave you? Did you finish it?

GARRY SHANDLING: (As Larry Sanders) Oh, yeah. I read it on the plane. Man, I can't believe Leno actually hid in the closet so he could hear the whole network meeting.

TORN: (As Arthur, laughter) It's a sickness to be so obsessed with what people are saying about you.

SHANDLING: (As Larry Sanders) I know. That is a sickness. What did people say about me not being mentioned much in the book?

TORN: (As Arthur) Everybody in town's talking about it.

SHANDLING: (As Larry Sanders) Good.

GROSS: Judd Apatow, welcome back to FRESH AIR. This new book and your documentary - the book is a loving tribute to Garry Shandling. It's also about how a comic turns insecurity and emotional suffering into comedy. Garry Shandling practiced Zen meditation as a way to deal with his stress, insecurity, emotional pain. And because of that, because he was so into Zen Buddhism, you assumed he didn't hold onto much in terms of, like, possessions and sentimentality.

So after he died, when you went into his house, you were surprised by all the stuff that you found there pertaining to his life. Tell us a little bit about what you found that you've worked into your documentary about him and now the book.

JUDD APATOW: I went to his house. And you know, there's the immediate question of - what do you do with all his stuff? And I, just as a friend, you know, was willing to help the family deal with it. And as a hoarder, I was interested in it not being lost because, to me, everything about Garry was valuable and is valuable. He wasn't sentimental. And so, for instance, all of his awards were in a trophy case that he built next to his washer and dryer.

GROSS: (Laughter).

APATOW: It's, like, his Emmy and his Peabody - they're all in this little trophy case in the most disrespectful place in the house, and that's what Garry felt like. He also didn't have any photos of family anywhere in his house. And I just assumed that he didn't care about any of that stuff and tossed it all. And when I started opening closets and looking in boxes, I realized that he didn't throw everything in the garbage; he threw everything in boxes and just chucked them in closets.

So for instance, his brother died when he was 10 years old. And I'd never seen a photo of his brother, but then I would open a box, and there would be a hundred pictures of his brother. So I don't know if he had a secret nostalgic or sentimental side, but he did keep everything.

GROSS: And he kept his journals, which he started in the 1970s. And you write that when you found Garry Shandling's journals, you wondered if it was OK for you to read them, if you'd be either violating his privacy or if you'd find out things about him that would make you like him less. But you decided to read them. Did it change your impression of him?

APATOW: Oddly, it changed my impression of him in the sense that I already admired him, and I knew he was a man who struggled, but I was surprised that 30 years of journals mainly contained Garry trying to talk to his positive voice. So they weren't journals from the point of view of someone who was just trying to spew all their toxic stuff. A lot of us write in journals like that. We just want to get the bad voice out of our head, and that's not what Garry's journals were like. They were a voice talking to the panicked, anxious voice.

So most of the journals were reminders to try to get out of ego, to try to be more kind and loving, to let go. And it's 30 years of reminders about the type of person that he wants to be.

GROSS: How would you describe Garry Shandling's place in comedy?

APATOW: Garry always cut his own path. So when he did "It's Garry Shandling's Show," there really hadn't been a show like that that was so experimental and weird and which made fun of the whole concept of sitcoms.

GROSS: Yeah, just describe the show.

APATOW: Well, the show was Garry playing, you know, a version of himself. And he basically would look directly into the camera and talk to the audience at home, and he would comment both on the show, the story and the mechanics of making the show. So he might suddenly jump on a golf cart and drive through the studio and reveal the studio audience and the warm-up person and the director, while still doing the story of that episode.

And then he did "The Larry Sanders Show," which was a satire of talk shows. It was a behind-the-scenes look at a anxious, neurotic talk show host somewhat like Garry. And in it, he tried to explore the way show business and ego prevents people from connecting and loving each other. That was his premise. And in a way, he was trying to use the show to explore his own psyche. And I always thought he was mocking the part of himself that he didn't like, mocking the person that wanted to be rich and famous and someone who could hold this high position for a long time.

GROSS: You knew Garry Shandling really well, but your first encounter with him was when you were in high school, when you were 16. And you had a radio show in which you'd interview comics, and you'd somehow manage to get really great comics to talk to you, a high school kid, on this tiny, little high school radio station. And we talked about that on one of your visits to our show. And you have a whole book collecting some of your high school interviews with comics. But anyways, you interviewed Garry Shandling when you were 16 in 1983, and this was about five years after he first started doing comedy. It was about two years after his first appearance on "The Tonight Show." How did you get Garry Shandling to talk with you?

APATOW: Well, back then, there wasn't an Internet, at least none that we knew about (laughter). And most comedians didn't do long-format interviews. There were no podcasts and - other than maybe some morning radio to promote gigs. So I interviewed about 50 comedians, mainly by tricking their publicists into thinking that it wasn't a high school radio station, that it was just a normal radio station. And most publicists, because these comedians didn't do many interviews, were very willing to let me talk to them.

Garry was in Vegas, I think, opening for Joan Rivers when I did this interview, and he had just hosted "The Tonight Show" for the first time, which was very rare for a young comedian who wasn't that famous to get to host "The Tonight Show." And what I remember about the interview was he was just really funny and was very willing to talk about how jokes are written and then tell me a bunch of jokes to show me the process. And it was one of the interviews I appreciated the most.

And you know, looking back, it's weird because he completely changed my life. He hired me to write for his show. He did a cameo on the pilot of "The Ben Stiller Show," which I thought was part of why we got picked up. He asked me to direct; I had never directed before. So it's weird that I knew him for so long. It almost feels predestined, our relationship, and then, ultimately, being able to tell, you know, the story of his life.

GROSS: Your book about Garry Shandling has just been published. In your earlier documentary about him, "The Zen Diaries Of Garry Shandling," you play a short excerpt of that high school interview you did with Garry Shandling. So let's listen to this. This was recorded in 1983, when you were 16.

(SOUNDBITE OF FILM, "THE ZEN DIARIES OF GARRY SHANDLING")

APATOW: How would you describe the type of humor that you're doing?

SHANDLING: Oh, man.

APATOW: Because it's not that conventional. It seems that, you know, when you watch it, it's, like, your ideas on things, and I think it's great.

SHANDLING: I do this joke in my act, that I've heard every excuse for a woman not going to bed with me. I think I've heard them all. I remember this one girl actually said to me, look - not with this Falkland Island thing.

(LAUGHTER)

SHANDLING: And I said, that was over a year ago. And she said, I still haven't gotten over it yet. And I said, well, I can understand that, Mrs. Thatcher.

APATOW: (Laughter).

GROSS: (Laughter) OK. That's a brief excerpt of my guest Judd Apatow's interview with Garry Shandling when Judd Apatow was in high school. Did that interview help lead you to have enough of a connection with Garry Shandling that he would be willing to help give you your start in comedy?

APATOW: (Laughter) I'm so excited to talk to him. You could just hear it in my voice.

GROSS: Oh, absolutely.

APATOW: I could not believe it. It's - you know, it's like I'm talking to, you know, John Lennon. And I didn't ever tell Garry about it when I first met him. I think I waited a very long time to tell him (laughter) that we had met over the phone.

GROSS: Oh, he didn't realize. He didn't put two and two together and say, oh, you're the kid who - no.

APATOW: No, I was so embarrassed about it. And I met him because he was looking for jokes for the Grammys. He was hosting the Grammys. And my manager connected me with Garry. And Garry said, well, you know, send me some jokes. And I stayed up all night and wrote, like, a hundred jokes because I really felt like, I think this is the big break of my career. And he liked the jokes enough to hire me on in a more serious way. And then he took me to New York to be at the Grammys with him and on stage during the show.

And I don't think I wrote many jokes that he used. I wrote a lot of setups for jokes, and then he would get rid of my punchline and write a better punchline. And I think that that was helpful to him, that I knew music and I knew the vicinity of a joke.

GROSS: Well, let's take a short break here, and then we'll talk some more. If you're just joining us, my guest is film director, screenwriter, TV and movie producer Judd Apatow, and his new book is called "It's Garry Shandling's Book." We'll be right back. This is FRESH AIR.

(SOUNDBITE OF MUSIC)

GROSS: This is FRESH AIR. And if you're just joining us, my guest is TV and movie producer, writer and director Judd Apatow. The person who gave him his break in comedy was Garry Shandling. And Judd worked with Garry Shandling on projects, and now a couple a couple of years - like, three years, I guess, after Garry Shandling's death, he has a new book editing things from Garry Shandling's life, his journals, interviews with other people about Garry Shandling, interviews that Garry Shandling gave during his life. And it's called "It's Garry Shandling's Book."

Garry Shandling grew up in Tucson because his older brother needed a warm, dry climate because he had cystic fibrosis, which is a genetic progressive disease in which mucus clogs the airways in the lungs and makes it increasingly difficult to breathe. And Garry's older brother Barry died at age 13. Garry was 10 then. And it sounds, from your documentary and your book, that it traumatized Garry when Barry died and left scars that never went away. And I mean, he wasn't told that the end was imminent. He didn't get a chance to say goodbye. He wasn't taken to the funeral. How did that affect him?

APATOW: You know, it's hard to know for sure, but it certainly scarred him in a way that affected him throughout his life. After his brother died, the family dealt with it by not talking about it, which I think, you know, for that time period - this was 1960 - is something a lot of people did in post-World War II America. They said, all right, we're going to move forward, and how we survive this is we are going to stuff it down deep and not talk about it. And so throughout Garry's life, he was all for being honest and open and vulnerable and present and real. And I think that's because at the key moment of his childhood, people were not real with him.

GROSS: I want to read a journal entry from his diary in 2005.

(Reading) 'Cause before brother, you were a happy boy in your body - his death was a mind-F event and disappointment you had to deal with on your own. Go back into the body. Don't try to avoid pain. It is a struggle to stay in the body for everyone - discipline, breathing, confusing.

So he's still trying to deal with this. And it still seems to be - like, in 2005 - to be kind of shaping how he wants to get by in the world, to like be - you know, go back into your body. Don't try to avoid pain. This is a common struggle. You have it, too.

APATOW: Yeah, it's heartbreaking to hear that. And I think Garry was trying to understand how the death of his brother affected his life and his choices. And he knew that he hadn't dealt with it in the way that he should have. And so at the end of the documentary, there's a long letter that he wrote to his brother in which he basically says goodbye to his brother in a way he didn't get to in life. And it's just so beautiful and so sad.

GROSS: Do you want to read some of that?

APATOW: Well, he says at the end - (reading) goodbye from this world. Goodbye from the pain of your body. I honor your life. What a special short life to affect me so severely for so long. Thank you. See you on the other side. I love you.

GROSS: Well, it's clear you still find that very moving. That really speaks to you.

APATOW: It - you know, I was, you know, going through his things. And I had this idea that his brother, who he didn't ever talk about, might be, you know, the key to a lot of his personality. And then one day, I just stumbled upon that letter. And I just think, you know, it's so sad and also so beautiful that he got to a place where he understood it and could express something so deep and loving. And it's heartbreaking 'cause, ultimately, it's a little boy who had loved his brother so much. There was all this home video. And in every shot, Garry looks like he is in heaven with his older brother. And so, you know, it's - you know, it's the worst possible loss for a little kid.

GROSS: It sounds like Garry Shandling was also really shaped by a near-death experience that he had when he was in a car accident in Beverly Hills and nearly died. So he was 27 when this happened, and he writes about it in his journal.

And he says - (reading) remember when you were hit by the car? Death was in your face. And you realized just to live, even with nothing, is a more than fair trade. What do you need? Nothing. If you had everything, you would still have to face death. Don't be attached to life. Let go of everything. See what's left.

I think that's an example of what you were talking about earlier - him giving advice to himself and using his Zen voice, his calm voice to talk to himself. That was a turning point for him - wasn't it? - when he was in that traffic accident. Didn't he change his life and his - what he wanted to do with it afterwards?

APATOW: He was writing for sitcoms like "Welcome Back, Kotter" and "Sanford And Son" and doing some stand-up, but he wasn't that committed to it. He was having a hard time finding himself. And after the car accident, he decided to quit writing and focus all of his time on his stand-up. So it had a big effect on him.

GROSS: My guest is screenwriter, producer and director Judd Apatow. His new book is a tribute to Garry Shandling called "It's Garry Shandling's Book." And it's a companion to Apatow's HBO documentary called "The Zen Diaries Of Garry Shandling." We'll talk more after we take a short break. I'm Terry Gross, and this is FRESH AIR.

(SOUNDBITE OF BRAD MEHLDAU'S "HAPPY TUNE")

GROSS: This is FRESH AIR. I'm Terry Gross. Let's get back to my interview with Judd Apatow, who's produced and/or directed films and TV shows like "Freaks And Geeks," "The 40-Year-Old Virgin," "Superbad," "Anchorman," "Bridesmaids," "Girls," "Trainwreck," "The Big Sick" and "Crashing." He's edited a new book about Garry Shandling built around interviews, photos, jokes, letters and journals Apatow found in Shandling's home after his death in 2016.

Shandling was a mentor and friend to Judd Apatow and taught him about comedy, how to write, direct and mentor other young comics. The book is called "It's Garry Shandling's Book," and it's a loving tribute to a highly neurotic comic who practiced zen meditation while trying to turn his insecurity and neuroses into comedy. It also tells the story of Shandling's life. The new book is a companion to the HBO documentary Apatow made last year titled "The Zen Diaries Of Garry Shandling."

Garry Shandling came of age in comedy during the period when, if you wanted to make it big, you had to do "The Tonight Show" with Johnny Carson. It was the only late-night show. And it was really, like, the only venue where you were going to get a national audience, and people were going to hear you - your name. So in your documentary about Garry Shandling, you play a clip from Garry's first appearance on "The Tonight Show." So I thought we should hear that clip.

(SOUNDBITE OF TV SHOW, "THE TONIGHT SHOW STARRING JOHNNY CARSON")

SHANDLING: I ate dinner last night at a friend of mine's house. And he has - what do you call those things - a baby. He has a baby. And...

(LAUGHTER)

SHANDLING: (Laughter) I'm a single guy. I don't know how to relate to this too well, you know? And the baby's crawling around on the carpet, and this baby loads up his diaper, you know? And...

(LAUGHTER)

SHANDLING: ...I'm sitting there, you know. And the mother comes over and says, isn't that adorable? Brandon (ph) made a gift for Daddy.

(LAUGHTER)

SHANDLING: Now I'm figuring this guy's got to be real easy to shop for on Father's Day.

(LAUGHTER, APPLAUSE)

GROSS: OK. That was Garry Shandling's first "Tonight Show" performance. So, you know, it's funny. It's so not - like, anybody could have told that joke. You didn't need to be Garry Shandling to tell that. It's a - it's not a personal joke. It's not something that really comes out of his experience. So it's just interesting since he became so personal as a comic, since he did two shows that were basically a comedy version of his life with him playing himself, it's such a really big journey that he took comedically.

APATOW: I can only equate it to something like music. You know, the Beatles start out, and they do "I Want To Hold Your Hand" or "Love Me Do," and then it turns into "Sgt. Pepper" (ph). And, you know, that joke is - you know, it's a - it's, you know, a solid joke. There's been so much comedy since then that it seems mild at this point, but Garry was a great joke writer, a great writer of one-liners and bits. And he evolved into something that was much deeper and more heartfelt. But like a lot of people, it starts out with something simpler.

GROSS: So in talking about how Garry Shandling went from, you know, telling jokes that other comics could tell to doing stand-up that was much more personal, that's one of the things I asked him about when I interviewed him in December of 1992. And he was supposed to show up at a studio, but we got a call from his publicist saying that he had car trouble and that he couldn't make it. So we just did a phone interview.

But anyways, I was talking to him here about, like, developing his voice in comedy. So let's hear a short excerpt of that. Now, I should mention you include an - I'm honored to say you include an excerpt of this in the documentary version of your story about Garry Shandling's life. So thank you for including that.

APATOW: Thank you.

GROSS: (Laughter) So here's an excerpt.

(SOUNDBITE OF ARCHIVED NPR BROADCAST)

GROSS: When you started doing stand-up, did you have a sense of who you wanted to be on stage, you know, like, what aspects of your own personality you really wanted to bring out for your stage persona?

SHANDLING: It was really a nightmare. I had no idea who I was when I started, and I was frightened to death and had no natural performing skills. I'd never performed before in my life. And to be thrown onto the stand-up stage is an experience that you cannot fathom until you're actually there because there's no place to go. And everyone's looking at you, and you can't even see them because of the lights. And yet, you have to manage to start talking and be funny on top of it.

And at the beginning, I think I did - I wrote material that was very much influenced by Woody Allen, who's my favorite. And I used to do very offbeat jokes that sounded like I was reading them. And it took years to develop a style.

And actually what happened is I was involved in a relationship, and the girl left me. And I was very hurt - very hurt - and I had to go up on stage. And I finally just turned to the audience and said, this girl left me. I said - well, I said, what happened is she moved in - I - she moved in with another guy. So I dumped her because that's where I draw the line.

GROSS: (Laughter).

SHANDLING: And so that was the beginning - that was really the beginning of, you know, people - of the Garry Shandling dating years...

GROSS: (Laughter).

SHANDLING: ...In stand-up that came out, you know, because I realized, oh - I started to really spill my guts about being hurt, and people really related to it. And then - and it just was one of those things. It was in a nightclub in Dallas. I really remember it very well.

GROSS: You know, I think that's so interesting how uncomfortable he was on stage at the beginning and how it - he felt like he sounded like he was reading his jokes.

APATOW: And Mitzi Shore, who owned The Comedy Store, was very direct about the fact that she thought he was a terrible performer. And she didn't like writers who tried to do stand-up. So Garry, you know, couldn't really get in at The Comedy Store. And he - then he just started doing gigs at all these little crappy places in the Valley. And he didn't come back to The Comedy Store for a year. And then a year later, he came back, and he had found his voice and his confidence. And then they let him be a regular at The Comedy Store.

But it is interesting that sometimes just one joke unlocks the key to your whole approach. You know, he had one joke that was very honest and based on his suffering, and then he realized, oh, this is the way. I go down this path.

GROSS: So Garry Shandling became a frequent guest on "The Tonight Show" and then became one of the most popular guest hosts of "The Tonight Show." But he decided - Garry Shandling decided to stop doing "The Tonight Show," which is really surprising because he was guest hosting so much. I mean, it was such a privileged position to be in. But he gave it up. How come?

APATOW: Well, Garry was doing "It's Garry Shandling's Show" at the same time. And Garry just got tired. He just said, I can't do a great job at both of those things. I think the pressure to do work that was great just was almost unbearable to him.

GROSS: The pressure other people put him - put on him or the pressure he put on himself?

APATOW: I think he put it on himself completely. And he just had a bar he was trying to reach, and it was almost maddening to try to reach that bar. He just didn't mail anything in. He was obsessed with doing something unique and amazing, and I think it's exhausting in a way that people can't really understand when your mind works like that. If you care and you're passionate and you're soul-searching, it's also a very painful, compulsive process.

GROSS: Well, let's take a short break here, and then we'll talk some more. If you're just joining us, my guest is film director, screenwriter, TV and movie producer Judd Apatow, and his new book is called "It's Garry Shandling's Book." We'll be right back. This is FRESH AIR.

(SOUNDBITE OF ABRAHAM INC. SONG, "TWEET TWEET")

GROSS: This is FRESH AIR, and if you're just joining us, my guest is writer-director-producer Judd Apatow, and he got his start with movies like "Superbad" and "The 40-Year-Old Virgin." And one of the people who gave him his start in comedy back when he was really young was Garry Shandling, and now Judd Apatow, about three years after Garry Shandling's death, has published a new book that he edited called "It's Garry Shandling's Book" that includes interviews about Garry Shandling as well as a lot of excerpts from Garry Shandling's diaries.

You worked with Garry Shandling on "The Larry Sanders Show," in which he played a late-night talk show host. It was kind of like a satire of "The Tonight Show" with a producer who is similar to "The Tonight Show's" producer and an announcer who is similar to "The Tonight Show's" announcer, except everything is very funny and very satirical. So you were a writer and then one of the showrunners for the Garry Shandling show. When he asked you to be a showrunner, you were afraid to take the job. It was apparently a very stressful position, and apparently, working for Garry was very stressful. And you expressed your reluctance, and you said to him, I don't want you to hate me. What made you think that if you became the showrunner that it would kill your relationship with him?

APATOW: Well, there was just a long line of bodies of people who had held that position. I always liken it to trying to paint with Picasso - that if you were painting a painting with him, he probably, at some point, would turn to you and go, you're doing it all wrong. What's with the red? You know, you would always disappoint him because the show is so in his mind, and it's so based on his feelings and experience that when you work on something so personal, how could you ever know what he would do, what's in his heart, how he would behave?

And because Garry was, you know, neurotic about running a staff and he wasn't amazing with the writers and compassionate of what was so hard about pleasing him - that it was a combative show. It was painful at times. If you pitched Garry a joke and he hated it, you would feel it. You would - I mean, it would hurt you, the look of disappointment in Garry's eyes. And there were very few people that Garry felt like could write the show, so when he said, hey; could you do me a favor and co-showrun (ph) this last season?, I was terrified because I loved my relationship with Garry, and I didn't want something to go terribly wrong with it. And I said to him, Garry, I'll do it, but you have to know how hard this is. I was just honest with him in a way that probably no one ever had been, and I was honest about why he was difficult to work with.

And I said, let's figure out how we can do it where we don't turn on each other. And a lot of it was about trying to pull Garry into spaces to get him to have a little more time to figure out the solutions and to make the work more fun for Garry so he wasn't just waiting on the writers to hand him solutions. You know, how could we get him more involved in the process at certain key moments? And, you know, it worked pretty well. We remained friends at the end, and he really liked the final season. Adam Resnick also ran the final season. It was brilliant.

So it is one of the great accomplishments in my life. One of the funny things is when I was reading Garry's diaries, I kept thinking, he never slams me in these diaries. I was so happy. And then one day I opened the diary, and there was a list of everyone who had disappointed him that year, and I was number three...

GROSS: Oh, gosh.

APATOW: ...Because I left the show one year to go make a movie and I wasn't there to help him. So I think it hurt him more than he let on.

GROSS: But it wasn't your performance as a comedy writer as - the fact that you have to do something - a project of your own.

APATOW: Yes, and I didn't even know that he cared that I was there at that point. I was young and a consulting producer. I wasn't really in charge of anything. I was just pitching jokes and trying to be helpful. But I guess that hurt his feelings.

GROSS: OK, so he got sick toward the end of his life. Garry Shandling got sick toward the end of his life. He had hyperparathyroidism - I'm not sure what that is - and pancreatitis, and I'm not exactly sure what that is either. But - so what are those conditions, and how did they affect his outlook on life and his ability to function?

APATOW: Well, the thyroid issue affected, you know, Garry's brain. It slowed him down, and someone described it to me as almost mirroring what aging feels like. So there were years where Garry felt like he was running out of gas or he was getting old. But actually, he had this condition which was fogging up his brain. And he ultimately had an operation that dealt with it. But I think as a result of it not being dealt with for a long time, it may have contributed to pancreatitis, which is cysts on his pancreas. And he had to have a - you know, a life-threatening operation to deal with that.

And part of the result of all this was that he did get foggy in his brain. He had years where you would see Garry and he would just seem like a mess. And you didn't really ever know what it was. What - was it from being sick? Was he on medication? Was he depressed? And we all worried about him. And Garry, you know, would say to me, sometimes - how do I seem? You know, what are people saying about me? What do they think's going on? And he had an awareness of it. And he was always trying to get more clear-headed, but he was fighting multiple illnesses.

GROSS: He died on March 4, 2016. He was 66 years old. Do you remember your last conversation with him?

APATOW: In the month before Garry died, he was obsessed with getting "The Larry Sanders Show" on HBO streaming. He wanted it to exist somewhere. And we would talk and strategize about how to make that happen because it had been sold off in pieces to different entities. And he was trying to get HBO to buy all of it and to make it accessible. And he wasn't sure if HBO was the place or not. And I said, well, what is the issue, Garry? Is it money? Are you trying to find the place that will pay you the most money? Or you just want to have it out there for the most people to see? And he said, I just want people to be able to watch it. And we had a bunch of conversations about how to expedite that process.

And the morning that he died, he got a call. And his agent told him that HBO had closed the deal and they were buying "The Larry Sanders Show," and they were going to run it. And a few hours later, he died. And I'm not a believer that Garry knew he was going to die and that's why he was obsessed with getting the show seen. But it certainly was strange that he was so concerned with that issue at that time.

GROSS: I should say, although we talked about the hyperparathyroidism and pancreatitis, that's not what killed him in the end - or at least it wasn't the final thing that killed him.

APATOW: He died of a blood clot that moved from his leg to his heart. He had major dental surgery in Hawaii, and he flew back home. And it - there - it may have been the result of his other medical problems that this developed.

GROSS: Well, let's take a short break here, and then we'll talk some more. If you're just joining us, my guest is film director, screenwriter, TV and movie producer Judd Apatow. And his new book is called "It's Garry Shandling's Book." We'll be right back. This is FRESH AIR.

(SOUNDBITE OF DIGABLE PLANETS' "REBIRTH OF SLICK [COOL LIKE DAT]")

GROSS: This is FRESH AIR. And if you're just joining us, my guest is TV and movie producer, writer and director Judd Apatow. The person who gave him his break in comedy was Garry Shandling. And Judd worked with Garry Shandling on projects. And now a couple of years - like, three years, I guess, after Garry Shandling's death, he has a new book editing things from Garry Shandling's life - his journals, interviews with other people about Garry Shandling, interviews that Garry Shandling gave during his life. And it's called "It's Garry Shandling's Book."

You had to give a eulogy, and I assume you wanted to give a eulogy at his memorial service. And several comics, including Sarah Silverman, Kevin Nealon gave eulogies. And you had to decide whether to be serious or funny. Tell us how you decided what tone you wanted to take, and then we'll hear what you had to say.

APATOW: I - you know, sometimes, you're just so grief-stricken that you don't even know how something got done. You don't know how you wrote a speech or put together a memorial because you're just in a weird fever of sadness. You know, I think we all felt that the best way to honor Garry would be to make a speech that was, you know, heartfelt and funny - that Garry would want it to be funny. And you know, it's something that it's hard to look back on and know how we got through it. So I just tried to be sincere and do it in a way that I thought would make Garry laugh.

GROSS: OK. So here's Judd Apatow's eulogy at Garry Shandling's memorial.

(SOUNDBITE OF ARCHIVED RECORDING)

APATOW: It's been very emotional to go down the rabbit hole of Garry. But I feel like it's a lesson for me to just think very deeply about Garry's life and his death and to learn from it. It's odd that Prince just died because Garry and Prince were very similar.

(LAUGHTER)

APATOW: There really were no differences when you really get down to it.

(LAUGHTER)

APATOW: Garry was the prince of comedy.

(APPLAUSE)

APATOW: He was mysterious, complicated, sexually ambiguous. His talent was endless. He was a brilliant performer who may or not have been high the entire time. He had great hair. Both stood up against the man to get their [expletive] back, and both were sexy as [expletive]. "Larry Sanders Show" was Garry's "Purple Rain." "It's Garry Shandling's Show" was his "Dirty Mind." The only difference between the two men is that Garry had a huge [expletive].

(LAUGHTER)

APATOW: That is the joke Garry would have wanted, and we know that.

(APPLAUSE)

GROSS: That's Judd Apatow eulogizing Garry Shandling, and that excerpt is included in the documentary that Judd Apatow made about Garry Shandling, "The Zen Diaries Of Garry Shandling." So, I mean, I can hear you tearing up at the same time you're trying to say some funny things about Garry. Was it hard to hold it together while you were doing that?

APATOW: Well, I didn't hold it together (laughter). I just had to get through it. You know, Garry had so many friends. There were a thousand people at his memorial service. It was really a beautiful event. And I made a few documentary pieces that were about five minutes long showing moments from his life and interviews with Garry, and that's what made me want to do the documentary because in just preparing those I realized that that there was a story that people would like to hear and an inspiration in his life.

And I think Garry wanted to try to find a way to figure out how to tell people about everything that's in the book and in the documentary. And he hadn't figured it out yet, so to me, a lot of this work is, you know, completing something that Garry had started.

GROSS: So before we recorded our interview, I went to see if you were on Twitter and what you've been tweeting about. And what you've been...

APATOW: Oh, my God (laughter).

GROSS: What you've been tweeting about is Trump - Trump, Trump, Trump. Like, lots of retweets about Trump, lots of links to articles about Trump. It sounds like you're in a very political frame of mind right now, as are many people in America. Anything you want to say about that, about how absorbed you've become politically, judging from what you're doing on Twitter?

APATOW: Well, I follow it too closely. My wife decided to not watch the news that much, and she is getting younger by the day.

GROSS: (Laughter).

APATOW: She's regenerating. She looks like Millie Bobby Brown; I look like a wartime president. I'm going gray fast. It's all collapsing. But I do feel like these are scary times, and we have to speak up. Something really awful is happening. You know, we talk about all of the, you know, possible reasons for impeachment. How about just lying 10,000 times? Like, do we actually need more than that? Separate from our differences and how we should handle the economy or taxes or health care, don't we just want a person that doesn't lie 10,000 times?

And I hope to encourage people to register to vote and to get other people to register to vote. You know, the percentage of people who vote is so sadly low. And we do have all the power to change things and get better people in charge of our government, but people need to do the work to figure out how to vote, to make sure their vote isn't suppressed - which is happening. So I'm hopeful that people will go to the polls when it's time.

GROSS: Judd Apatow, it's been great to talk with you again. Thank you so much.

APATOW: Thank you.

GROSS: Judd Apatow's new book is called "It's Garry Shandling's Book." Tomorrow on FRESH AIR, my guest will be Andrew Marantz, a staff writer for The New Yorker and author of the new book "Anti-Social: Online Extremists, Techno Utopians, And The Hijacking Of The American Conversation." He reported on the alt-right during and after the 2016 presidential election. I hope you can join us. On this Veterans Day, we send our gratitude to those who have served and our thanks to the families who have made sacrifices while a family member served. We'll close with music performed by the Bay State Winds, the clarinet quartet of the Air Force Band of Liberty.

(SOUNDBITE OF MUSIC)

GROSS: FRESH AIR's executive producer is Danny Miller. Our technical director and engineer is Audrey Bentham. Our associate producer of digital media is Molly Seavy-Nesper. Therese Madden directed today's show. I'm Terry Gross.

(SOUNDBITE OF MUSIC) Transcript provided by NPR, Copyright NPR.