The Zen Diaries of Garry Shandling Is an Intimate Portrait of a Comedy Pioneer

Garry Shandling and Judd Apatow.

“It’s a show about people trying to get love, and shit gets in the way.”

That’s how the late Garry Shandling described his groundbreaking sitcom The Larry Sanders Show, an inside-showbiz series about the office culture surrounding a talk show. But the line also sums up the life of Garry Shandling as described by his friend, collaborator, and showbiz pupil Judd Apatow in his two-part documentary The Zen Diaries of Garry Shandling, premiering Monday night on HBO.

Apatow’s long (four-and-a-half hour!) tribute to the TV pioneer is the best, most focused thing he’s done since Freaks and Geeks. Zen Diaries is an intimate documentary about the man and his work, drawn from an extraordinary array of personal material, including home movies of Shandling’s childhood and adolescence in Arizona, photographs from every phase of his life, lengthy scenes and behind-the-scenes clips from The Larry Sanders Show and It’s Garry Shandling’s Show, and excerpts from the handwritten diaries he kept from the late 1970s until his death in 2016. The diary entries have a personality all their own. As pictured in tight closeups, one or two phrases at a time, they’re art objects in themselves, as if somebody recorded a lifetime’s worth of muttered comments into bathroom mirrors and transcribed them in cursive.

Shandling, for those less familiar with his work, was part of a wave of 1970s, Los Angeles-based comics who made stand-up more lifelike and less shticky. He created Showtime’s It’s Garry Shandling’s Show (another all-time great) and Larry Sanders, which has been credited with inspiring dozens of other sitcoms, including both versions of The Office. He was the first person to be named permanent guest host of The Tonight Show, then one of the most prestigious gigs in television. His C.V. is impressive enough, but where The Zen Diaries really excels is in its understanding of his psychology.

Shandling was born in Chicago and raised in Tucson, Arizona, where his family moved because his older brother Barry had cystic fibrosis, and his parents thought the dry, warm climate would be better for him. Barry’s death at just 10 years old is the “Rosebud” of this production, if not of Shandling’s life. His personal trajectory feels like a response to that formative tragedy, in particular Shandling’s laid back yet painfully confessional form of stand-up comedy. His family wasn’t repressed, necessarily — not in the stereotypical 1950s way — but like a lot of Americans, they had trouble talking about their feelings. There was tremendous pressure to just keep pain to yourself and soldier on so as not to be a bother to anyone. It’s clear that once Shandling got older, entered therapy, and became interested in Eastern religion (meditation in particular), he started to realize how unhealthy this was, and built his style of comedy as a cathartic, liberating response. “I had no one that I recall putting a hand on my shoulder and saying, ‘This is death. It’s okay to grieve,’” Shandling wrote in his diaries.

We see the seeds of this philosophy in his teenage fascination with ham radio operation. He had radio buddies in countries all over the world, and became very close to a Japanese boy who ultimately came to Tucson as an exchange student. This tendency to want to reach out across a void of space and seek closeness also seems related to the loss of Shandling’s only brother, and it’s to Apatow’s credit that he trusts us to get this without hammering the point home too hard.

Every step into showbiz was an attempt to conquer his fears. Shandling initially set out to be an engineer, and was a good science student, but he was enamored with comedy and used to record himself doing stand-up routines (some of which we get to hear), and after a while he asked himself, per his diary, “What if I take that ability and apply it to something I like?” The subtext of mentorship — of successful people passing on their knowledge to the young and unconnected — is established in an early account of a 19-year-old Shandling driving several hours to see George Carlin perform in Phoenix, handing him several pages of material he’d written for him, and asking for notes. Carlin told him to come back the following night and gave him an honest assessment: You’re green, but there’s some good stuff here, and you should keep at it. Here, as elsewhere in the documentary, the production’s staggering archival reach pays off: Apatow shows us Shandling’s original typewritten pages, and then, by way of old black-and-white photos, superimposes them on a tabletop in the green room of the Phoenix club where Carlin performed.

At every step, Shandling’s career is marked by intellectual restlessness and a work ethic that sometimes shades into masochism or arrogance. He never wanted to be the most famous or highest paid, though he certainly wasn’t averse to a big paycheck or top billing. He wanted to be seen as being different from everyone else, more special, fresher, more daring. That’s what led him to study physical performance to become a good stand-up comic, as opposed to a writer who just happened to work in clubs, too. It’s what led Shandling to study acting, so that he could express himself in a different way, and learn about his own psychology by playing other people. It’s what led him to give up The Tonight Show gig when it became clear that he couldn’t do that and It’s Garry Shandling’s Show at the same time and do both jobs to the best of his ability. (The sitcom won out over the hosting gig because he was in control of the sitcom and could do whatever he wanted; plus, the Tonight Show job was repetitious.)

The Zen Diaries series goes into some detail about Shandling’s 1998 financial mismanagement lawsuit against his former manager and producer, Brad Grey (who was not interviewed before his death last May, although he shows up in archival footage and pictures). There’s also a lot of material in the second episode about how difficult and dark Shandling could be, and how insecure and petty. (The low point is when he fired his girlfriend and Larry Sanders Show co-star Linda Doucett shortly after they broke up; she sued him for wrongful termination and won a settlement.) But for the most part, this is an affectionate portrait, not a muckraking exposé. Between the interviews (which include Apatow), the archival footage, and the diaries, it has a keener sense of its subject’s psychology than most productions of this type. Parts are so shockingly intimate that it feels as if we shouldn’t be seeing them, as when Doucett tells Apatow that their relationship ended because she wanted to be a mother and he didn’t want to have kids, a fear that friends attributed to the trauma of losing his brother. Doucett seems philosophical about the whole thing now, crying during her interview with Apatow and then adding, “We started off mocking the industry, and then we fell prey to it.”

Is there too much of a good thing here? Maybe. There are emperors, generals, and Nobel-prizewinner scientists who don’t get four-and-a-half hours on HBO, and it’s possible that we didn’t need a detailed segment about Shandling’s voice-over work on the 2006 animated film Over the Hedge (even though it ends up being a testament to his work ethic; he extensively rewrote his own dialogue and took the role of a turtle very seriously). Although Shandling completists will love the segment on the digressive, quasi-documentary DVD supplements he created for the Larry Sanders Show box set, others may wonder if it wouldn’t just be better to tell people how they can order them. (Though it’s a treat to see him carve up Ricky Gervais, who shows up for a hero-worshippy interview unprepared and oozing arrogance.)

Still, anybody who was inspired and moved by Shandling’s work won’t complain about being able to luxuriate in this exhaustive account. Even the slack portions are intriguing because of the access Apatow has to the records of Shandling’s time on Earth. There are photos of him as a kid with huge glasses and awkwardly fitting shirts, play-acting at being a stand-up comic or calling people on his ham radio. There are snapshots of him curled up in a hammock in fetal position on a beach while taking a sabbatical from show business, and outtakes of him directing episodes of both of his sitcoms (including one where he castigates himself in a torrent of profanity and the audience thinks he’s just doing a bit). There are sections of letters Shandling wrote to his mother, who smothered him because she used to have two boys and lost one, where you see him balancing the desire for privacy against the obligation to honor the woman who brought him into the world.

Best of all, there are the diaries, a record of a man who never got so complacent in his success that he forgot what was important. “There is no goal,” Shandling wrote 40 years ago. “This is it. This is life. The growing is life.”

The Zen Diaries of Garry Shandling Is an Intimate Portrait