I didn’t know Garry Shandling very well—certainly not like many of his fellow comedy writers and performers and even a few journalists that he befriended and mourn him today—but the terrible news of his passing on Thursday made me think back to an evening we spent together in Washington, D.C. sometime during the last century.

In late April 1989, I was a style writer for The Washington Post and Garry was heading into the final season of his groundbreaking Showtime sitcom, It’s Garry Shandling’s Show, which—being too cheap to pay for cable—I enjoyed watching reruns of on the local Fox station.

The guy was funny, and he was also an artist.

As a standup comic and the creator of a television series that subverted the time-honored sitcom format with a scathing yet hilarious take on his vocation, Garry was whip-smart, determined to the point of stubbornness, and self-lacerating (qualities he also possessed in real life, sometimes to his detriment) and, at least for me, irresistibly empathetic.

In the crafting of his jokes and storylines, he was a painstaking wordsmith and insightful observer of human eccentricities, including his own.

Showbiz was merely a metaphor for an existence that was frantically status-seeking yet epically insecure.

Garry Shandling, his neurotic character, somehow let his audience know that he knew, deep down, that life was precious and not to be frittered away, even if he couldn’t help himself.

It was the complex, many-layered, and above all intelligent sensibility that he’d later elaborate upon and master in his much-celebrated HBO series, The Larry Sanders Show, which has become a classic sendup of a peculiarly American life force—the late-night talk show—while never sacrificing authenticity for contrivance or easy laughs.

Anyhow.

At The Washington Post and many other news organizations stationed in the nation’s capital, the black-tie White House Correspondents’ Dinner was and is a rite of spring, prompting just the sort of savage human impulses in politics and media that Garry had been satirizing in his own line of work—mainly the cut-throat competition among and within the various newspapers, newsmags, and television, radio, and cable networks to snag celebrity guests for their respective tables, sort of like taxidermy-ed grizzly heads mounted on a clubhouse wall.

So, after getting approval from my bosses, I phoned Garry’s Los Angeles publicist and extended an invitation.

Within minutes, Garry himself called back and—in that immediately recognizable nasal voice—peppered me with pointed questions about the purpose of the dinner, who comes, what happens, and could he bring his girlfriend.

I tried to explain that the president of the United States—in this case George Herbert Walker Bush—shows up to tell jokes, and tout Washington dutifully laughs and laughs even if the jokes aren’t funny.

I was a tad nervous and tongue-tied.

“You didn’t expect me to call you directly, did you?” Garry noted, correctly gauging my surprise that he had blithely discarded the PR infrastructure that was his just due as the star of his own eponymous TV program—to speak to a reporter, no less.

The momentous day arrived, April 29, and around lunchtime, I went to Garry’s downtown hotel to deliver the embossed dinner tickets that would allow him and his longtime girlfriend, a beautiful Playboy model and actress named Linda Doucett, to get past the Secret Service’s magnetometers and into the eerily blue-lit basement ballroom of The Washington Hilton.

I found them off the lobby in the dining room, eating and talking in hushed tones, and as I approached their table, Garry looked up at me tensely—a glint of irritation in his eyes—as if braced for another autograph hound about to intrude on his day. I sometimes strike people like that, I guess.

I introduced myself, and Garry relaxed. He said he was a bit sad. One of his idols, Lucille Ball, had died a few days earlier and Garry was still in mourning.

Even worse, when they’d landed at around midnight at Dulles Airport 13 hours earlier, the limo his people ordered had failed to show up—and they waited around for an hour until finally deciding to take a cab.

What was more, Garry kvetched (“If you keep using Yiddish expressions with me, I’m going to have to stop talking to you,” he warned), they were both jet-lagged and sleep-deprived.

I tried to cheer them up by reminding them I’d arranged for a VIP tour of the White House that afternoon, and actually they should probably get going.

Garry and Linda arrived a bit late for dinner and a little discombobulated.

I wondered if somehow they had gotten lost and if the place cards I had so carefully arranged at our table—seating Linda next to one of the most powerful men in the country, the dour, unsociable and slightly odd senior senator from West Virginia, Appropriations Committee Chairman Robert Byrd, and putting Garry, Washington dinner-party style, on the opposite end—would go for naught.

Garry perused my handiwork, muttered, “Are you kidding me?” and seated himself next to Linda; and other than an awkward hello, neither them uttered a word to the old man for the rest of the evening, which seemed just fine by Byrd.

I don’t remember anything about our conversation nearly 27 years ago, except that Garry kept noticing many of the most pompous, self-congratulatory media types and politicians that Washington had to offer and making me and Linda laugh.

As dessert arrived, a beefy Secret Service agent came up to our table, and instructed Mr. Shandling to follow him through the throng.

Here, I’ll let my former Washington Post colleague, Martha Sherrill—who covered that dinner for the paper—pick up the narrative:

After seven minutes of joking, Bush yanked TV comedian Garry Shandling from behind a curtain and had him work the crowd pro bono.

Bush introduced him as “an average American tourist” who’d been pulled from the White House tour line. Nobody in the jaded crowd of news types, quite frankly, believed him. O ye of little faith.

Truth is, Shandling and girlfriend Linda Doucett had flown in from L.A. and were taking a VIP tour of the West Wing earlier in the day. And as they were lurking outside the Oval Office—kind of gawking at it—Bush turned up unexpectedly.

“The president walked in,” Shandling said yesterday on the phone, “along with Mrs. Bush and their dog. They came right over and said hello—much to my amazement. And he asked me what I was doing in town, and I said I had been invited to the correspondents’ dinner.”

Bush suggested to Shandling that they do a routine together. “I thought he was just joking,” said Shandling. “Because—as I said on stage—I’ve never really taken him seriously before.”

Later Saturday afternoon, Shandling returned to the White House and sat around with Bush, his aide Tim McBride and speech writer Edward McNally.

“We went over his jokes,” said Shandling, “then I mentioned a couple jokes that I was thinking of doing. He was especially warm and friendly. It was a very easy atmosphere.”

At the Hilton, Shandling recounted his visit, saying, “I was in line at the White House. It was the liberal line—which is the line that has to pay,” and he included a plea he’d made to the president: “I hope you won’t ask me to do that State of the Union thing.” Bush closed their act. “It’s getting late,” he said, “and fortunately there won’t be time tonight for my slide shows of the trip to Honduras.”

After it was all over, and the president’s entourage departed the hotel, we pushed our way through the crowd toward the escalator and the exit.

When a stout woman in a champagne prom dress with mum corsage approached Garry and complained that she just didn’t believe that he’d simply showed up at the White House for a tour and ended up on the dais with Bush—that instead, like most things in Washington, it was clearly a conspiracy—Garry seemed genuinely outraged.

“I’m sorry you feel that way. That is what happened,” he insisted, and turned away.

As we strolled down Connecticut Avenue, back toward Garry and Linda’s hotel, he was giddy, and thanked me profusely for making his amazing adventure possible—and I was happy to take credit, however baseless.

Some months later, Garry called to thank me again when he received a coveted invitation to a White House state dinner and for years afterward I’d see him occasionally in L.A. or New York, until we fell out of touch, except for tweeting greetings at each other once in a while.

I felt sure that one day, we would meet again, and maybe jog each other’s memories about his fateful journey to Powertown.