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This June 29, 2010 file photo shows David Letterman riding a go kart powered by the reaction from mixing 648 Mentos candies into 108 two-liter bottles of Coke while taping a segment for "The Late Show with David Letterman" in New York.

Charles Sykes/AP

Fast cars, cigars and women. That defined David Letterman for a while.

Now he is defined by something else – his age, his crankiness and ornery, vinegary style of humour. He's going because it's time. He won. He outlived Jay Leno and lived to see a much younger opponent, the callow, cheery, affable Jimmy Fallon arrive as his late-night nemesis. Not that he cares much, probably.

There was a time when Letterman was super-cool – back in the 1980's, when Letterman was a strange creature of late-night TV. Back then, nobody knew much about him. He was on NBC at 12:35 a.m., when only the college kids watched and the urban hipsters, but before anyone called them "urban hipsters." The viewing audience was small but appreciative. Stunned a bit by this odd-looking man orchestrating an hour-long mockery of the conventions of television.

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He looked happy doing it. A perpetual grin on his face, unforced and real. He had this guy, Larry "Bud" Melman, who arrived and did readings and solliloques, deadpan-weird send-ups of sincere television. Watching, you didn't know whether to laugh or cringe. The band on the show played frantically, and you figured everybody was stoned. You felt stoned, watching it.

It was like a secret. And it was, in a way. Famously, Letterman's NBC show was unwatched by the network executives. They'd gone to bed. Back then, nobody in power cared much what unfolded after The Tonight Show ended. Then, of course, word spread. David Letterman was weird, inspired, talented and, given the adoration he inspired, a player.

The press took notice and probed. Turned out Letterman liked driving fast cars, smoking cigars and he had this effect on women. Not that super-models flocked to him. It was more that young, smart, funny women liked him. And he liked them. He had this geek charm that made women like him a lot.

Thirty years later, as Letterman announces his departure in 2015, the things that once defined him cool cast a shadow over his career. He won, but he's old now. A codger. Hard to believe, but he'll be 68 when he retires next year. Undone, in the late-night wars, by youth. What made his career, that youth-appeal, decimated by a factor he cannot control – age.

In his prime he was sublime. Much as he admired Johnny Carson, he was the anti-Carson, the anarchist of late-night. Before the Internet, before Twitter and viral videos what Letterman did was legendary but spread by word of mouth. Saying "Letterman" was like using a code. Those who knew his show knew what was cool.

He grew, of course. He grew into the show CBS gave him to compete with The Tonight Show. He grew assured, older, cranky, occasionally vicious and often unsettling in his hang-ups and hates. His loathing of Mitt Romney reached a level of visceral contempt that could make viewers uncomfortable even as they laughed.

And, it has to be said, in the end, quite a few things about Letterman made people uncomfortable. The markers of his storied career now make him look peculiar, all too human. He did emerge from the battle to replace Carson on The Tonight Show elevated and undaunted. While Jay Leno maneuvered and wheedled, Letterman had the dignity to walk away, march over to CBS and start anew. But the mystery-man of fast-cars, cigars and women became a man of perplexing oddness.

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He dropped the cigar smoking after emergency surgery for a quintuple bypass, something he turned into sketches on his show. It was an event that made him look very vulnerable, as did a later admission that he was missing from his show because of a severe case of shingles. Most peculiar of all was Letterman telling his audience in October of 2009 that he had been the victim of an extortion attempt by someone threatening to expose his sexual relationships with young female members of his staff. Everything about these matters was uncool. What he still had was his wits, but the wits of a senior citizen.

I met him once. It was 1994, during one of my first visits to LA for the TV critics press tour. Letterman was a year into his CBS reign and riding high, pummeling Jay Leno's Tonight Show in the ratings. I was walking into the hotel when Letterman appeared beside me, returning and sweating from his morning run. He was in shorts, t-shirt and a cap. I stared. He looked at me and asked, "TV critic?" I nodded yes. "That's a job I could do," he said. As we walked through the hotel corridors he asked how many of us were attending the event and if I'd tried the hotel food. "I wouldn't," he wisecracked. "Not if CBS is paying for it." He advised me to be wary of the yoghurt, and smacked his stomach,

People he encountered who recognized him in the hotel he addressed as "Bill." To several people he just said, "Hey Bill, how ya doing?" We waited together for an elevator. I asked gawkily if he could give me a preview of his presentation to the TV Critics, scheduled for an hour later. He looked down at me and said, "I might take a nap and just forget about doing that." People gathered, stared at him and the elevator came. We all stood in it, in silence. When Letterman exited, he said aloud, to no one in particular, "Well, that was weird." To me he gave wink said, "See ya later, Bill."

He had the aura of a college guy, funny and charming but unknowable. Weird.

The cigars are gone and who knows now about the women? Maybe he still drives fast cars, but as a TV guy, he's a jalopy now. Old, of an earlier pre-Internet era. His last year could be his best, though, because he's still weird.

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