On March 24, 2016, Garry Shandling died suddenly of a heart attack at age 66. Not only did he leave behind a tremendous legacy as one of the most influential, successful comedians of all time, he left behind a generation of comic minds inspired by his pitch-perfect sense of self-deprecating, challenging humor. Judd Apatow, lifelong friend and protege of Garry’s, was one of them, and his HBO special The Zen Diaries of Garry Shandling (which aired this past week in two parts) serves as a brilliant eulogy for its subject, and an intriguing investigation of the effect he had on those whose lives he touched most.
Over the course of four and a half hours, Zen Diaries tracks Shandling through the course of his entire life – from his childhood in Chicago (where he lost his beloved brother Barry at age 10 to cystic fibrosis) to his early days as a stand-up, progressing to the heights of his career as the mind behind subversive, deconstructive TV hits like It’s Garry Shandling’s Show! and The Larry Sanders Show. Later, we see Shandling’s subsequent fall from fame and the readjustment of expectations that came with it. As a comic and a human being, Shandling contained multitudes – he practiced Buddhism, meditating before every show; he never married or had any children; he was constantly restless about his comedy career and the direction of his life.
As the title implies, Apatow uses Shandling’s lifelong collection of handwritten journals and diaries as the structure for his documentary. It’s a strategy which offers the deepest insight yet into a comic who regularly mined his own life for comic material. Amid stock footage of standup acts or TV shows, or Apatow’s many interviews with Shandling’s friends, family, and collaborators, Apatow frames these stages of his mercurial, unconventional life with scribblings of Shandling’s most intimate thoughts and feelings (occasionally narrated by Michael Cera when investigating the man’s childhood), revealing a man maddeningly in touch with his emotions and anxieties. “Am I funny?” he asks himself after bombing at a gig; around the time of his mother’s death, he writes, “the fact of death is as common as a tree.” That transparency was essential to Shandling’s work, the man feeling that authenticity is the secret not only to great comedy, but an honest life. The best comedians mined their material from an essential core of truth, and Zen Diaries reveals this innate understanding of self as key to his insight.
In some ways, though, Zen Diaries isn’t just about Shandling’s life, but about Apatow’s relationship to Shandling, and the role that he played as both comedy mentor and father figure. “In a lot of ways, he was a mystery to me,” says Apatow early in the doc, and Zen Diaries seems like an earnest, heartfelt attempt to explicate one of the most important – and inscrutable – people in his life after their death. To his credit, Apatow doesn’t impose himself overmuch in the documentary, but he makes the most impact in front of the camera during his interviews, functioning more as casual conversations between comedy contemporaries (including fellow Shandling acolytes Kevin Nealon, Sarah Silverman, and Sacha Baron Cohen) than investigative reporting. That’s to the doc’s credit, of course; it’s fitting that such a glowing eulogy of a man so beloved by those in the comedy world would function as a series of solemn, wryly funny two-person wakes. (One highlight is Apatow’s deceptively funny rapport with David Duchovny, longtime friend and on-screen flirt with Shandling; for more on their friendship, read Michael Roffman’s recent interview with Duchovny.)
Despite Apatow’s swell of love for his subject, it’s so refreshing that Zen Diaries doesn’t become a lovefest for Shandling. Even those he loved knew he was a complicated guy – a man plagued by ego, insecurity, and a deep, abiding sense of neuroticism that made him as funny as he was difficult to work with. From his acrimonious split with fiancée Linda Doucett (which coincided with her removal from The Larry Sanders Show) to the rift that formed between him and his manager Brad Grey, Zen Diaries reveals a surprisingly dark side to Shandling, a capriciousness borne of his own neurotic desire to always keep moving.
While the documentary’s first installment is optimistic – shining a light on Garry’s rise to fame and the way his brother’s untimely death (and a near-fatal car accident in his youth) spurred him to make the most of his life – it’s the second half that shows the chinks in Shandling’s armor. Apatow is uncompromising about the artistic sacrifices Shandling had to make to keep The Larry Sanders Show afloat amid an array of changing showrunners, as he is the man’s abortive attempt to become a movie star with What Planet Are You From?. (It must be a real disappointment for an actor to learn that Mike Nichols can’t stand you after one day of shooting.) Shandling always strove for greatness and never rested on his laurels, but found himself listless when his new directions didn’t always work out.
In the middle of all this is Apatow – the son that Shandling never had, trying to put the pieces together to form a picture of the man he felt so close to, but never really understood. The film never gestures toward a sense of journalistic objectivity, Apatow’s approach making clear from the opening frames this is a post-mortem (literally) of a comedy icon investigated from within the confines of the comedy world. At times, he lingers too much on previously filmed segments – the final hour plays the lion’s share of his Comedians in Cars Getting Coffee episode with little editorializing – but this just betrays his sincere and infectious love for the man, which pours through the screen and translates to the viewer. Even if you don’t love Garry Shandling more after watching this doc, you’ll at least understand a bit more about the many dichotomies the man existed in – Buddhist spiritualist and ambitious careerist, generous mentor and rage-filled taskmaster.
Zen Diaries comes away with a fascinating, complex portrait of a man as unpredictable as he was hilarious, a comedy pioneer who lived in constant terror of being forgotten and ignored. Shandling’s life was one of myriad conflicts, many of them with himself; it’s this sense of multiplicity that Apatow captures with incredible alacrity over the ensuing four hours. Through his affectionate eye, and those of the dozens of comedy masterminds he cultivated and inspired, you get an idea, however brief, of how it must have been to be a friend and contemporary to someone so beloved.