Gary Shandling’s life and art are both given the redeeming appreciation they deserve.

“The Zen Diaries of Gary Shandling.” Photo: HBO.

By Matt Hanson

It might sound strange to viewers of a certain age but Garry Shandling, the subject of HBO’s epic two-part documentary The Zen Diaries of Gary Shandling, has a stellar reputation, not unlike Robert Johnson’s in music or Kurosawa’s in film: he’s your favorite comedian’s favorite comedian. Shandling brought a cerebral, alternately confessional and diffident approach to traditional standup. It’s normal for comics to create a recognizable stage persona that may or may not be based on their private lives, but Shandling took his comedic persona a crucial step further. Despite his willingness to make himself the butt of most of his own jokes, presenting himself to the public as the ultimate schlemiel, The Zen Diaries shows how Shandling’s humor came from a complex comedic mind that was constantly, obsessively at work.

Lovingly directed by lifelong friend and showbiz mentee Judd Apatow, the documentary features an impressive roster of comedy legends testifying to Shandling’s singular genius. Conan O’Brien and Sacha Baron Cohen both remark that it seems as if the meta-heavy humor of “It’s Garry Shandling’s Show ” (Shandling’s first foray into a live action sitcom) had been written just for them. Generating postmodern wit out of a theme song that ruminates on the circumstances of its own writing (“This is the theme to Garry’s show/ the theme to Garry’s show/ Garry called me up and asked if I would write the theme to Garry’s show”) rejected blasé audience pleasing in favor of stimulating hipper, more sophisticated audiences. It was a risky choice, but the best way to influence the art form as a whole.

The film gives us a deep look into Shandling’s family life. His beloved older brother Barry died of a cruel and unavoidable illness while barely in his teens, but like a lot of ’50s-era families the tragedy was never discussed. Shandling’s mother, who inspired her surviving son’s love of comedy, held a tight emotional hold over her remaining son for the rest of his life, which resulted in Shandling writing quite a few more (and better) take-my-mom-please! jokes than those of your average open mic hack.

Being that close to tragedy so young must have surely taken a toll, but at times the documentary leans a little too heavily on explaining everything via psychological motivation. Shandling also got into a near-fatal car accident after moving to LA to be a comedy writer; he had out-of-body experience where a voice asked him if he wanted to continue to live Garry Shandling’s life. He responded in the affirmative, obviously, but spent the rest of his life convinced that life was ultimately an illusion, eventually taking up meditation and studying Buddhism.

Known for his writing on shows like Sanford and Son and Three’s Company before becoming a performer, Shandling kept a diary throughout his life and made it accessible for the film. Reading a stranger’s diary is an awkward experience; it feels extra intrusive when the subject is a performer. Comedians walk a very precarious emotional line. They are called on to get laughs from strangers as a matter of survival, but a joke can bare the soul. We read Shandling’s anguished notes to himself as a young comedian about staying in the moment, staying committed to your joke, and working at remaining as natural as possible onstage. It’s a master class for any aspiring comic in what it takes to do standup at the level that Shandling (and few others) reached — eventually he was subbing for Johnny Carson on The Tonight Show and was the first in line to replace the legendary host upon his retirement. He courageously declined the offer, wanting to pursue more creative projects, which became the pioneering It’s Garry Shandling’s Show and his magnum opus, The Larry Sanders Show.

Given our media-saturated, self-obsessed culture, the brilliant meta-fictional construction of The Larry Sanders Show feels almost prophetic now. Shandling plays the titular character, the late-night TV host he could have been, whose charm and wit are constantly at odds with his showbiz-provoked insecurities. The show isn’t just a glimpse at the ego-fest and constant self-doubt that is part of nightly entertainment — in a voice over, Shandling explains that it’s really about people needing love and the families they create to find it. Larry Sanders is more than a projection of what Shandling could have been: the documentary shows us how, in many ways, it’s who he really was. Great talent vying with epic neediness.

Many of the celebrities who appeared on the show play themselves, or at least slightly altered versions of themselves, an innovative trick that set the stage for subsequent shows like Curb Your Enthusiasm and for reality TV as a genre. Maybe because they’ve been exposed to it their whole lives, modern audiences have learned to distrust the kind of self-invention that created the legends of old Hollywood. Now we want some semblance of the real person behind the scenes. Part of the brilliance of Larry Sanders was in exploring how difficult it is to understand the difference between a person’s self-image and their reality. The fact that the show won a Peabody award —  the highest award in journalism — only underscores how far-seeing it’s ontological schizophrenia really was.

With the show’s success, the overlaps between Shandling’s fictional world and his real life began to blur. His long-time girlfriend Linda Doucett, who played a key role in the show, tired of his squeamishness about marrying and having children and finally broke up with him. Her character was subsequently written off the show, resulting in her suing him for sexual harassment and wrongful termination. Shandling’s aversion to commitment seemed to combine lingering problems with intimacy and the usual guy’s hesitance about shacking up with lifelong fascination with attaining Buddhist non-attachment. There’s a great real life running gag in the film about the house he was always perpetually building and re-building, in order to put off having to decide whether or not to settle down.

The problems got worse when his close friend and longtime manager Brad Grey, who had taken him on as one of his first clients, was discovered to be triple-dipping into the show’s profits. He was also luring writers away to help start other projects of his own. Business is business, but Shandling felt deeply betrayed and counter sued for millions. His diaries show his disgust and pain about being double-crossed. For a guy who had spent the past few years comedically analyzing the venality of show business, this surprising act of double-dealing must have hit hard. He eventually won the suit for an undisclosed sum without the case ever going to trial.

Shandling’s last years were remarkably quiet. He didn’t work often, but whatever he did had to be done over and over until it was perfect. Interestingly, the film shows us how, for the bonus features on the Larry Sanders DVD, Shandling decided to meet with the people who helped inspired their characters in real time. It’s an uncomfortable but riveting experience, watching him reinitiate contact with his old flame Sharon Stone over breakfast, who once appeared on the show as Larry’s old flame, only to see how Stone still remembers his foibles and peccadilloes quite well. It becomes even more cringey when he sits down with Linda Doucett and she matter-of-factly lays out how Garry couldn’t rise to the emotional occasion. The look on his face as he stares at the floor is hard to watch. As funny as the show was, these painful conversations proved that there were real human emotions at stake.

By the end, however, Shandling’s life and art are both given the redeeming appreciation they deserve. After his unexpected early death, the comedy community and Shandling’s friends and family rallied to give him a touching send off. Shandling’s comedic legacy is undeniable — he’ll always have his autographed picture on the wall of the Comedy Store, along with the likes of Jay Leno, Robin Williams, and David Letterman, who chose to have more mainstream careers. Ricky Gervais and the writers for The Simpsons testify to how Shandling’s commitment to awkwardness opened doors for them comedically. Friends like Apatow, Kevin Nealon, and Bob Saget gave speeches at his funeral that mixed their real grief with jokes that were accurate, hilarious, and worthy of Shandling’s own roots in standup. A perfect sendoff for a man whose comedy was less of an illusion than his actual life.

Matt Hanson is a critic for The Arts Fuse living outside Boston. His writing has appeared in The Millions, 3QuarksDaily, and Flak Magazine (RIP), where he was a staff writer. He blogs about movies and culture for LoveMoneyClothes. His poetry chapbook was published by Rhinologic Press.