HBO

Garry Shandling’s Complicated Love Story

A new HBO documentary reveals how the revered comic dealt with intimacy — not with romantic partners, but with his male friends

Garry Shandling was unashamed to tell his straight male friends that he loved them. When he and Jerry Seinfeld would meet up, for instance, they’d hug and Shandling would say, “I love you.” Similarly, when Shandling appeared on the Late Show in 2007, he informed David Letterman that he loved him. That same year, Shandling released a DVD box set of his iconic HBO series The Larry Sanders Show, and one of the extras involved the comic hanging out with his good friend Tom Petty, who mentions, “You were saying the other day about how you don’t call people and tell them that you love them, basically, as much as you should — ‘cuz we’re all getting older — and that we should tell each other these things.”

In the entertainment business, it’s common for people to throw around the L-word (often to demonstrate phony enthusiasm and/or unearned closeness). But with Shandling, who died March 24, 2016, at the age of 66, that familiar proclamation never felt insincere. He said it because he meant it — and also, maybe, because he needed other people to say it to him.

The superb new HBO documentary The Zen Diaries of Garry Shandling is, in some ways, a fairly standard portrait of a revered comedian. Over the span of four-and-a-half hours over two nights, the film recounts Shandling’s life and legacy, hitting all the highlights of his career, interviewing those who knew him best, and even offering up a Rosebud-like explanation for why he was such a complicated person. (Shandling had an older brother, Barry, who died of cystic fibrosis when Garry was 10 — a death, The Zen Diaries argues, he never got over and which informed some of the intimacy issues he had the rest of his days.)

But if its structure is familiar, its depth of feeling is rare, perhaps because the emotions contained in the film feel unresolved — both within the man being memorialized and for those who knew him. The Zen Diaries is a platonic love story between straight men, and what’s remarkable is how it captures just how fraught those relationships can be.

The documentary is the brainchild of Judd Apatow, who idolized Shandling since Apatow was a teen, convincing the stand-up to be interviewed for his high-school radio show. Soon, a friendship developed, with Shandling enlisting him to help write material for his early-1990s hosting gig on the Grammy Awards. From there, Apatow was invited to work on The Larry Sanders Show, in which Shandling played a lightly fictionalized version of himself as a miserable, ego-driven talk show host.

Shandling was a key figure in Apatow’s career, but in The Zen Diaries, the filmmaker admits that he never felt like he truly understood the guy. “For 25 years, he was the most important mentor that I had,” Apatow says early on. “And he was always there for me — personally, professionally — but in a lot of ways, he was a mystery to me.” The documentary, which uses as its narrative spine excerpts from Shandling’s journals that he started in 1977, plays like Apatow’s attempt to seek understanding — as well as closure.

He’s not alone in this quest. The film is filled with famous friends with great affection for Shandling — including fellow comics Kevin Nealon and Bob Saget — who attest to the fact that they were never sure which Garry they would encounter, either the warm, happy guy or the mercurial, self-critical one. His journals echo that split, sometimes containing positive self-affirmations about the importance of forgiveness and living in the moment — he meditated all his life — and angry assaults on himself and others. (In interviews, Apatow has mentioned that, while reading the journals in preparation for the documentary, he was relieved that he never ran across his own name — only to flip the page to discover that, at one point, he’d been ranked No. 3 on a list of people who had disappointed Shandling.)

It’s hardly news that a brilliant performer wasn’t always fun to be around, but The Zen Diaries doesn’t use Shandling’s dark side as its driving force. Instead, Apatow chronicles how his mentor tried to transcend that darkness to become someone who could be close to people. Shandling didn’t always succeed. (He was engaged once, to longtime girlfriend Linda Doucett, but the fear of commitment and fatherhood was too much for him.) Nonetheless, The Zen Diaries illustrates how he tried to make peace with being able to love people in his life, and for them to love him.

Shandling’s act was filled with material about his romantic woes, but the man we hear about in the documentary doesn’t seem to be wrestling with his inability to find a soul mate. Rather, Shandling was fascinated by people’s struggle to be present — and their fear of stripping away affectation and letting their vulnerable, true self emerge. For him, intimacy wasn’t about sex or romantic love — it was about making a meaningful, almost spiritual connection with the people around him.

On a superficial level, this need to connect was central to the appeal of his first series, the groundbreaking It’s Garry Shandling’s Show, which launched in the fall of 1986 and tore down sitcom conventions in order to show the audience that it was all artifice. Shandling would talk directly to the camera, constantly reminding the viewer that his home was just a set on a soundstage.

The struggle to be real was even more pronounced on his follow-up, The Larry Sanders Show, which invented the template for the modern comedy series: no laugh-track; no hackneyed three-camera setup; and an emphasis on blunt, awkward, messy reality. However, while The Larry Sanders Show was hailed for its skewering of celebrity culture, the show was, for Shandling, about something more profound.

“[Sanders] really needed love and wanted love and he was capable of giving love,” Shandling once said, “and all of this bullshit of our silly, impermanent lives that get in the way is represented in this show.” In the same interview, he noted that he screened Larry Sanders for a Vietnamese monk, who instantly understood why Shandling juxtaposed Sanders’ smiling, ingratiating persona during the talk show segments with the vain, neurotic nightmare who emerged during the backstage sequences. “Everybody should be the way they are in front of the camera, where they’re open and loving with nothing at stake,” the monk explained to Shandling. “But behind the curtain, everything is at stake, and it drives them crazy.”

For Shandling, daring to be close enough to people to really be open and loving was the goal — but also incredibly perilous when he felt others had wronged him. The Zen Diaries goes into detail about his ugly professional divorce from his longtime manager and friend Brad Grey, who helped bolster his profile in the early days but was later sued by Shandling for $100 million, the comic asserting that (among other things) the manager took advantage of their relationship to further his own career and took more than his share of the Larry Sanders profits. The New Yorker’s Tad Friend chronicled the split at the time, reporting that Shandling pal Warren Beatty once had lunch with Grey to see if he could foster a reconciliation. It’s revealing that this is what Grey said Beatty told him: “This is simply a case of Garry feeling you didn’t love him enough.’ And I started, foolishly, to say, ‘That’s just not true!’ And he said, ‘No, no, no, no. It doesn’t matter what you think. He thinks you didn’t love him enough.’”

That sense of betrayal — of being unloved — haunts The Zen Diaries, which is littered with instances in which Shandling felt people let him down. Writers and crewmembers were fired from his shows when they didn’t meet his standards. (Alan Zweibel, who co-created It’s Garry Shandling’s Show with Shandling, tells Apatow of the falling-out they had near the show’s end, in part because Shandling thought he was disloyal.) Friends caught in the crossfire could be just as easily spurned. An emotional Saget recalls that Shandling stopped speaking to him after the Grey imbroglio — Grey had been both men’s manager, and Shandling believed that Saget had chosen Grey over him simply by remaining a client. “I had two friends that I loved who were basically going through a very upsetting divorce,” Saget tells Apatow. “And I couldn’t not be friends with Brad anymore. But I also couldn’t not be friends with Garry anymore. But that’s what Garry wanted.”

While Doucett is interviewed for the documentary, as are a few female colleagues, The Zen Diaries, like a lot of Apatow movies, is very much a dude-fest that’s obsessed with the intricacies of male bonding and how men try (and often fail) to express emotions to one another. In that way, Shandling is perhaps a perfect subject for the sentimental bromance master Apatow, who never fully let go of the father-son dynamic of their friendship, despite how successful Apatow became. (When he made his first film, The 40-Year-Old Virgin, it was Shandling who helped find the ending.) Apatow isn’t the only performer who looked at Shandling as a mentor: Everyone from Conan O’Brien to Sacha Baron Cohen to Lone Survivor director Peter Berg hold him in similar esteem, and they talk fondly about what a giving, supportive person he was.

Obviously, there’s a lot that’s funny in The Zen Diaries, but there’s plenty more that’s emotional as Apatow and company suss out a tangle of anguish, regret, sadness and confusion over the loss of their difficult, big-hearted friend. Lots of straight men have trouble articulating their feelings for other men. But this clearly wasn’t a problem for the people who knew Shandling. Openness was part of the deal with him — an ideal that he strove to attain, even if he often fell short. Yet the effort he put into it was the purest form of love he could give others.