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Watching HBO’s terrific four-hour documentary The Zen Diaries of Garry Shandling, it’s hard to tell if the film is a promising start to Judd Apatow’s next career as a nonfiction chronicler of comedy history and its psychology or if this was a one-off culmination of Apatow’s personal and professional journeys to this point.
That isn’t to say that Apatow turns Zen Diaries into an autobiography. Shandling was a essential and formative figure in Apatow’s life, dating back to a radio interview when Apatow was still in high school and through decades of active mentorship. It isn’t always the case that a filmmaker’s extreme closeness to his subject yields good art, but Shandling was a part of Apatow’s DNA and, through the documentary, Apatow makes it clear that Shandling was integral to the comedy DNA of multiple generations.
Air date: Mar 26, 2018
Presented over two nights, but easy to digest in a single sitting, Zen Diaries is a worthwhile account of Shandling’s career and evolving philosophy, an insightful exploration of stand-up comedy and the comedic voice, and a sad contemplation and reckoning from those Shandling left behind and those grappling with his legacy.
The opening chapter focuses primarily on the first two facets, tracing Shandling’s upbringing in Arizona, including the pivotal role played by the death of his brother, Barry. It’s a simple beginning, driven by a limited amount of photographic and home movie footage and by the speculative memories of a single cousin. It’s mostly there to set the foundation for Shandling’s relationship with his mother and the unresolved issues pertaining to Barry’s death before Shandling heads to Los Angeles and the documentary really gets fascinating.
Shandling’s stand-up beginnings at The Comedy Store are a perfect storm for Apatow and the doc because they combine a shocking amount of early stand-up audio and filmed footage and the opportunity to bring in friends and colleagues including Bob Saget, Jim Carrey and Jay Leno — plus they coincide with the start of Shandling’s diaries that give the documentary its name. Shandling’s scribbles, frequently narrated by Michael Cera, aren’t always profound — it’s a lot of vagaries like “The secret is be myself!” and “Am I going to wind up broke? I don’t know!” mingled with advice on how to handle hecklers — but they’re snapshots of waves of optimism and pessimism as Shandling’s celebrity advances. The audio and stage footage trace certain developing Shandling bits and give insight on the refining of his uniquely ironic and withering tone. And the talking heads marvelously explain how, with his own eccentricities, Shandling was part of their group, but maybe not always at home in their group — leaving very much open the chance that someday Apatow might do a documentary on the ‘70s scene currently featured in fictionalized form in Showtime’s I’m Dying Up Here.
The first night takes us through the deconstructive brilliance of It’s Garry Shandling’s Show and how the responsibilities from that series led him to give up a regular guest-hosting role on The Tonight Show, sacrificing a personal dream in a conflicted way apparently typical for Shandling.
These two hours, which also feature collaborators like Ed Solomon and Alan Zweibel, are the cleaner, more conventional part of Zen Diaries.
The second night becomes more personal, more painful, more deeply introspective and yes, in familiar Apatow fashion, more rambling and unfocused. Beginning with over 45 minutes on The Larry Sanders Show, it’s also much more ambitious.
The Larry Sanders segment, with Jeffrey Tambor, David Duchovny, Penny Johnson Jerald, Sarah Silverman and writer Peter Tolan among others, breaks down the difficult process of making one of TV’s most important comedies. From there, though, the doc has an additional 90 minutes of uncertainty that reflects how sometimes human life doesn’t have a clear arc.
There were the emotional and legal obstacles of Shandling’s split from longtime manager Brad Grey and the paranoia-inducing revelations of the Anthony Pellicano case. Apatow and various talking heads discuss why Shandling didn’t do another TV show, what went wrong with his film What Planet Are You From? and whether Shandling was happy. Some of those are little questions with simple answers — Mike Nichols and Shandling apparently just weren’t on the same page in their ill-fated cinematic collaboration — and some are obviously very big questions, getting at Shandling’s transition from identity crisis to identity acceptance. There’s a coming-to-terms that’s going on, both for the documentary’s subject and its filmmaker.
Shandling’s post-Larry Sanders life lacked a clear structure, and occasionally Apatow’s struggles to make sense of it are evident. For example, there’s a segment that’s almost nothing but Shandling’s appearance on Comedians in Cars Getting Coffee, which I would have watched if that were what I wanted to watch. Shandling’s interest in Buddhism, hinted at in the title, is never really given life, and it’s left to Sarah Silverman of all people to observe, “It’s not because he’s Zen. It’s because he was in desperate need of being Zen.” There’s a simultaneous need to give Shandling’s last years meaning and Apatow’s awareness that assigning a single meaning or revelation wouldn’t honor his friend.
If the second half of the doc feels padded and occasionally a bit too much like a prelude to a premature death, it’s still full of utterly exposed moments from the people who loved Shandling, starting with Apatow. You get Conan O’Brien remembering Shandling’s last visits to his late-night show and recalling how important he was after the fiasco of O’Brien’s Tonight Show departure. You get Bob Saget trying to make sense of how the Brad Grey separation left them estranged. You also get footage from Apatow and Shandling’s paired semi-standup appearances in his last years, the promises of a return that never quite materialized.
Mostly, The Zen Diaries of Garry Shandling justifies its sprawling form. It’s bittersweet, very funny and does right by the man and the comic world that gave him so much insecurity and so much success.
Airs: Monday and Tuesday, 9 p.m. ET/PT (HBO)
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