President Barack Obama and David Letterman/Official White House Photo by Pete Souza

A couple of weeks ago, I trekked into Times Square on a gloomy Thursday to pay homage to the king one last time. I was eleven when Dave took the spot after Johnny Carson, not quite old enough to watch it every night -- and we wouldn’t own a VCR to tape it for a few more years -- but at an age where I caught it occasionally. And it blew my mind.

I distinctly remember the first time I saw "Late Night"; it was at a sleepover at Trevor Smith’s house. I can’t recall who the main guest was, but I know that Charles Fleischer (you may know him as the voice of Roger Rabbit) was on because that dude was nuts. This was back when the Letterman show was pure anarchy and all kinds of loons made regular appearances, oddballs like Harvey Pekar, Andy Kaufman, and Crispin Glover, not to mention regular castmembers like Larry “Bud” Melman, whose bit where he greeted people at the Port Authority Bus Terminal still kills. Anything went. Be it Dave getting dunked into a vat of water in an Alka-Selzer suit or Chris Elliott taste-testing dog food.

It was glorious madness so steeped in tearing down talk show conventions that the typical descriptive ironic doesn’t do "Late Night" justice. And it seems most comedy fans of a certain middle age owe a debt to Dave for his influence, including another fellow who shacked up at Trevor’s house that night, my best friend/heterosexual life partner, stand-up comic Auggie Smith.

“I think that episode also had Chris Elliott doing ‘Guy Under the Seats.’ I had no idea what the hell was going on, but I knew I’d never seen anything like it before,” says Smith. For Auggie, it was the start of an obsession, one that would fuel his career choice. “I had a little television in my bedroom and since school wasn’t exactly a priority, I’d watch Letterman every night. What really drew me in was the stand-ups he’d have on his show: Bill Hicks, Mitch Hedberg, guys like that. I don’t think I ever saw a bad set and it wasn’t until I got into comedy that I realized there’s a lot of crappy comics out there.”

Writer Brian Abrams thoroughly covers the early anarchic days in his oral history And Now... An Oral History of “Late Night With David Letterman,” 1982-1993, for which he interviewed fifty people over six months. It’s an entertaining look behind the scenes at what was easily the coolest gig going, but it still left him with questions about the man at the center of the storm.

“I couldn't tell you the difference between Letterman’s persona and his image any better than before I started,” he says. “Dave's a mysterious one, yeah of course, but the impression I got from the "Late Night" alum was that his reclusiveness came from a sincere place. He didn't want to be photographed at parties or power lunches. And I definitely detected a sense of loyalty to him among the majority of staff. Maybe it was because writing for the hippest late-night TV show of its era was also the greatest job they ever had. Or maybe it means he's not the major sardonic asshole that everyone wants to believe. I have no idea.”

There have been plenty of magazine profiles and interviews, but after thirty-plus years and thousands of hours in front of us, David Letterman remains a mystery. You pick up bits-and-pieces about what he’s like, ranging from a generally sweet guy who finds celebrity distasteful, to your garden variety self-doubting neurotic comic type, to a full-born weirdo who doesn’t want people to look him in the eye, and everything in between. Basically what we know is what we see, but there have been shifts in Letterman's public face as he's entered his Yoda phase.

In the years immediately following the Letterman v. Leno "Tonight Show" mishegoss, when the former landed at CBS and the latter routinely kicked his ass in the ratings, Dave often seemed checked out and the show lost its spark. Until real life intervened. In 2000, Letterman underwent quintuple bypass surgery for a blocked artery. Upon his return, he brought out all of the medical staff, saying “these people saved my life,” giving one nurse in particular an uncomfortably long hug. They literally opened him up. It was the most human Letterman had ever been in public, until he became the first talk show host to return to regular broadcasts following 9/11. Initially reluctant to return and not knowing if the time was right for the "Late Show," he told the crowd that the courage of Mayor Giuliani and all of the first-responders inspired him to do so.

Letterman’s speech is incredibly moving, to me personally as a lifelong fan, a Manhattan resident, and a native Montanan, it's the one I go back to when I need it. One line in particular is seared into my brain forever, “We’re told they’re zealots, fueled by religious fervor, religious fervor ... And if you live to be a thousand years old ... Will that make any goddamn sense?”

While still generally unknowable, in these later years, he’s become more avuncular, conversational, and fun-loving. (He also quietly became one of the best interviewers on television, giving ample time to issues like climate change.) The man who once scared movie stars to death, who went toe-to-toe with the likes of Oprah and Madonna, has become a guy who is sincerely interested in his guests’ children. “It hasn’t just been the maturation of an entertainer; we’ve been watching a human being grow,” says Smith.

It was announced recently that the final "Late Show" will be May 20, 2015. It’s been one hell of a run at what will number at 6,028 episodes, and although the time feels right, it's still sad. The final Christmas show will air December 19, an annual affair that usually features Jay Thomas telling a story about getting stoned and driving around with the original Lone Ranger in the back of his car, Dave and others throwing footballs trying to knock a meatball off the top of a Christmas tree, and Darlene Love “blowing the roof off the dump” as the host used to say with “Christmas (Baby Please Come Home).” If you’ve never seen it, do yourself a favor, because in solidarity, Love is retiring the song from her repertoire.

Come 2015, you’ll start seeing a million “Thank You, Dave!” thinkpieces and against my better judgment, I’ll read every one of them. I’m going to try and savor his final months, but you can bet Letterman won’t be playing his swan song to the hilt. Tuesday night, he cut Ben Stiller off when started in on the hosannahs.

I want to share one story; it's secondhand, but it came from a reliable source. A former low-level guy who worked on the "Late Show" ended up alone on an elevator with Letterman and started an innocent conversation that didn’t really go anywhere. Later, he was chastised by someone higher up for even being on the same elevator as Dave. Some months later, that guy’s brother was in a severe car accident and had no health insurance. When they asked for the bill, it was covered. The guy has no idea how David Letterman even knew his brother was in the hospital.

Apocryphal? Maybe, but it’s the kind of enigmatic David Letterman tale that only he could answer. If he were to write a memoir, it would go gangbusters, and Larry Bud knows I’d be all over it. As Auggie notes though, “Some people don’t need to bleed all over the page about their dead father. Maybe Dave just wants to go out as one of television’s greatest entertainers, and we should all be happy with what he gave us and leave it at that.”

It started with the comedy, so ending it with comedy may be the way to go. After all, Letterman’s hero Johnny Carson more or less called it a day after leaving the "Tonight Show." I get it and I know how peacefully unencumbered small-town Montana life can be. On that note, I’ll leave you with one of my all-time favorite "Late Show" bits, “Dave and Steve’s Gay Vacation.”

Enjoy your retirement, Mr. Letterman.