Garry Shandling thought a lot about his craft, fretted a lot about how people would perceive and receive him. But be assured of this. His death Thursday at age 66 silenced one of the great comedic minds of the last quarter century.

Shandling seemed to have a classic case of the comic’s angst, never quite grasping how brilliant he was. And it definitely wasn’t an act. He wanted to be somebody -- just not that big of a somebody. I interviewed him several times over the years. It was always a challenge. Not because Shandling was "difficult," but because he more often than not seemed to be wrestling with what to say, how to say it and whether any of it made any sense.

His masterstroke, The Larry Sanders Show (left), ran for six glorious seasons on HBO. Its star-drenched 1998 extended finale still ranks as perhaps the greatest series sendoff in TV history. The likes of Jim Carrey, Carol Burnett, Warren Beatty, Ellen DeGeneres, Jerry Seinfeld, Sean Penn, Jon Stewart and even Tom Petty excelled as themselves opposite a fictional late night talk show host whose insecurities and vanity were all too believably real.

In a telephone interview shortly before the series’ 1992 premiere, Shandling wondered why anyone would want to be Johnny, Dave or Arsenio.

"The only thing odder than being on TV every night is wanting to be on TV every night," he said. "Imagine someone having the nerve to say to their guidance counselor, ‘I want a job that would put me on TV every night.’ "

Shandling said he eventually realized it wasn’t at all what he wanted. So he abandoned his quest to succeed Johnny Carson as host of The Tonight Show. Once a week on HBO would be more than enough, he decided.

"Each (real-life) host will watch this show and think we’re talking about them," he said. "I really think the show captures some general qualities that all talk show hosts have. For many of them, it’s easier to relate to talking to someone when you’re on television than when you’re not. I’m a pretty shy guy, but I don’t think I have the cold temperament of a talk show host. I don’t have the obsessive drive that most hosts have. Although I believe David Letterman doesn’t necessarily have an obsessive show business drive. That’s why his show is particularly good. He puts his creative side first."

Before Larry Sanders came It’s Garry Shandling’s Show (left), the "breaking the fourth wall" Showtime gem that pre-dated Seinfeld, which in many ways copied it. Premiering in 1986, it ran for four years. The then-fledgling Fox network re-purposed the last two seasons of the show before Lifetime began airing It’s Garry Shandling’s Show all over again in 1991 on the same night that his first comedy special for HBO premiered. This was news to Shandling. But he made the most of it -- comedically at least -- after his interviewer broke it to him during a hookup from his hotel room in Maui.

"Let’s guesstimate the number of viewers," Shandling said. "I’d say 10 to 15 people. I’d probably have a wider audience if my show aired in Kuwait. My guess is that within a year they’ll start airing it on some ham radio frequency. But heck, The Weather Channel could have bought it. That would have been worse."

This was Shandling at his self-deprecating best. But his neurotic tendencies were also kicking in again. He worried about picking too large a venue -- The California at Irvine Theater -- for the HBO special. He likewise was vexed about the comedy movie script he’d been working on.

"Hopefully, when I read it, I’ll like it and say, ‘Yes, I’d like to play this part.’ Or I could read it and go, ‘Who the hell wrote this?’ I’m going to keep working on it and explore any other projects that come along. I know that sounds really nebulous, but then I’m a Democrat."

The Larry Sanders Show soon came along, enshrining Shandling and co-stars Jeffrey Tambor and Rip Torn as sidekick Hank "Hey Now" Kingsley and producer Artie (whose last name went unmentioned). It ran for 89 episodes, was nominated for 56 Emmys but won just three. That only fed Shandling’s insecurities, leading to a rather bizarre presentation during the January 1998 Television Critics Association "press tour" in which HBO chairman Jeff Bewkes emphatically announced the final season of the show before bringing Shandling onstage.

"Excuse me," he began. "This is all news to me." He then noted that five new episodes already had been completed and that the last of them would be one hour in length. "If in fact, that is the end," he said before swiftly leaving a hotel ballroom with Bewkes and several HBO publicists in tow.

Yours truly caught up with this entourage and told Shandling that "HBO seems to be more certain about this than you. Last night they were saying you’d be here to announce the end of the show."

Shandling then rebooted: "You know, I guess it wasn’t clear. This is the last season of the show. And it’s being written that way. And it’s a moving season, a funny season. I’m sure I will miss it enormously. It has nothing to do with running out of ideas. It’s a show that continues to explore human behavior. And that’s bottomless."

He never starred in another TV series after The Larry Sanders Show ended with a comedic aria on the night of May 31, 1998.

"I once made love for an hour and five minutes," he bragged to applause during the HBO special. Pause, one-two. "It was on the day you push the clocks ahead."

We now know -- and have known for quite a while -- that Garry Shandling was well ahead of his time. His last TV appearance, on the Jan. 20 episode of Jerry Seinfeld’s Comedians In Cars Getting Coffee (above, left), was subtitled "It’s Great That Garry Shandling Is Still Alive."

He would have seen the humor in that. But it also might have driven him crazy.

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