Garry Shandling has died at 66. Here are some of the comedian's most memorable roles and appearances, including his hit HBO series, "The Larry Sanders Show." (The Washington Post)

Almost 23 years before his death, Garry Shandling sat down with David Letterman on the host’s second-to-last night on NBC for a late-night debriefing. The conversation could have been awkward, and definitely went beyond the latest celebrity chit-chat. After all, Shandling had just been offered $5 million to take over Letterman’s time slot, and turned it down. Now, the two men — one leaving a job he no longer wanted, the other unwilling to take it on even for a large amount of money —  contemplated the chair as they left it behind.

“Did you ever seriously consider — this all could now be yours,” Letterman said.

Shandling looked around the studio skeptically.

“Well, I like the clock,” he allowed. Not one to disappoint, Letterman had the clock removed, and gave it to Shandling. “Frozen on the moment of my last appearance,” Shandling deadpanned.

The remark, like much of Shandling’s comedy, was not-so-subtly cutting, and betrayed more than Shandling’s contempt for trite talk-show banter. It showed his desire — a philosophical, even religious desire — to search for something more, even if it meant doing fake late-night as “Larry Sanders” instead of real late-night as himself.

“I have to make a decision here,” he later said of the choice. “Is there a way that I can learn about myself and the world and people and what this is all really about and get down into that s— and the essence of people’s lives and how they cover it on a talk show? Or can I do it on a show about a guy that hosts a talk show?”

Despite having to turn down a lot of money, the choice proved easy.

“It isn’t about a guy who hosts a talk show,” Shandling, a Buddhist fellow traveler who survived a near-fatal car accident, said of “Larry Sanders.” “It was the ability to have that world within which you could tell the story of human beings.”

Shandling, of course, proved successful as an actual late-night host, guesting for no one less than Johnny Carson in the 1980s. But something about the job never seemed to sit right with him.

“When I hosted it for a week at a time several times, I started to wonder, because I found it incredibly draining and somewhat limiting in the sense that you’re really forced to talk to people that you would never talk to, or want to talk to, in real life,” he told The Washington Post in 1992. “I actually found myself saying to someone who was on `Dynasty’ how much I enjoyed that show. And then I couldn’t look at myself in the mirror the next morning.”

In the satirical world of “Larry Sanders” and as a guest on other people’s talk shows, Shandling delighted in pulling back the curtain to reveal the squeaky, ill-oiled machinery that makes celebrity interviews go. On Dennis Miller’s HBO show in 1994, he brought a list of questions about Miller’s monologue. “Where’s my camera?” he asked Charlie Rose in 1998. “It’s too dark in here.” (“Just pick one,” Rose, a bit derailed, replied. “They’ll find you.”) “I’m glad you were nice enough to tell everyone I’m plugging something,” Shandling, hawking a “Larry Sanders” DVD, told Letterman in 2007. In a recent episode of Jerry Seinfeld’s “Comedians in Cars Getting Coffee” — one startlingly titled “It’s Great That Garry Shandling is Still Alive” — Shandling asks: “When do we do the phone call that will be on air?”

It was this sort of puffery — de rigueur set-ups, ham-handed segues, an interviewer’s feigned interest — that Shandling found wearying.

“What happens on most talk shows … is that they’re entertainment shows,” Shandling told Rose — perhaps the most serious man in late-night. “… Nevertheless, you still must feel the necessary need to entertain. Otherwise, it becomes indulgent.”

Rose’s steely visage registered mild objection. After all, he hosts a talk show, even if it’s on PBS. And he said he just wants his guests to relax — to be themselves.

“What I would like for people to say after you come here,” Rose said, “… is to say, ‘I’ve never seen him that way and I found him interesting and different.'”

Shandling offered his objection in turn.

“But that’s a pressure in its own right,” Shandling said. “So now I feel pressured to be interesting. So what’s the difference between feeling pressured to be interesting and feeling pressured to be funny?”

In “Larry Sanders” and his other work, Shandling seemed to be looking for something more. Yes: His shows broke the fourth wall and allowed celebrities to spoof themselves. But unlike other series that wallow in irony and self-awareness — “Seinfeld,” “The Comeback,” “Curb Your Enthusiasm,” “Episodes,” to name but a few — Shandling’s had a mission beyond getting laughs: to be “a lab for the study of human behavior.”

“We didn’t have our name splashed on the studio door, because I didn’t want it to be thought of as a television show,” Shandling said.

If that sounded pretentious — what half-hour HBO comedy holds a mirror to the human soul? — Shandling seemed comfortable with his vision. He wasn’t above using the “L”-word.

“[Sanders] really needed love and wanted love and he was capable of giving love and all of this bulls— of our silly, impermanent lives that get in the way is represented in this show,” Shandling said.

Although Shandling was reluctant to be labeled a Buddhist, one can’t talk about impermanence without reference to the deity with the big belly. Shandling said he showed an episode of “Larry Sanders” to a friend — a Vietnamese monk with “a robe and shaved head and two burned off fingers.”

“He said, ‘Oh!'” Shandling recounted. “‘Everybody should be the way they are in front of the camera where they’re open and loving with nothing at stake. But behind the curtain, everything is at stake, and it drives them crazy.'”

Shandling was impressed with his Buddhist friend’s interpretation.

“He got it faster than anybody!” Shandling said. “I had to hire a bunch of monks to write the show. Because that’s what they’re struggling with.”

If this nuance — Larry Sanders as dharma’s premium-cable messenger — was lost on many, Shandling found it essential. He was looking for authenticity — even if it meant flopping in front of one of the world’s most famous religious figures.

In what turned out to be one of his final discussions, Shandling told Seinfeld about a meeting with the Dalai Lama during which he told His Holiness a joke about the Buddha. The joke: Why didn’t the Buddha get married? Because his wife would have said: “Are you going to sit around the house all day?”

When the Dalai Lama didn’t laugh, Shandling explained the joke. After a pause, the holy man declared: “Oh! Funny!” Like much of Shandling’s material, the zinger operated on many levels.

“That’s what you wanna do,” Shandling told Seinfeld. “You wanna have a three-minute gap from when you tell the joke to when you get the laugh.”

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