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May 21, 2015 By Matt Fink

Although I’ve never met him, I’ve spent more time with David Letterman than any man other than my father. For the last 25 years, five nights a week, he has entered my living room for an hour. Knowing that he will never visit again has left me with an almost embarrassing sense of a loss. No more Top 10 lists, no more stupid pet tricks, no more Paul Shaffer—it’s like a whole universe, 35 years in the making, has been swallowed up by a black hole. Not to be overly dramatic, but Letterman’s retirement feels like a death in the family. Uncle Dave is never going to drop by to tell stories and crack jokes again, and I don’t know how I’ll ever replace him.

I remember the first time I was exposed to Letterman’s humor. There was an NBC primetime special in the early ‘90s that presented some of the best sketches from Late Night, the massively-influential franchise he founded in 1982. I don’t remember much about it now, but there was a clip that crystalized everything that I would come to appreciate about Letterman’s humor. Walking through the halls where Late Night was taped, Letterman (literally) bumped into Abraham Lincoln, exchanged pleasantries, and soon was angrily chasing the venerated president down that same hallway when he discovered Lincoln had stolen his wallet. This was totally absurd and inexplicable humor, stranger and altogether more dangerous than anything that could ever turn up on The Cosby Show or Alf. Almost instantly, my 10-year-old brain was hooked, and I would spend my summers (and as many school nights as I could) trying to stay awake until 12:35 to catch the night’s Top 10 list, writing down as many of the entries as I could to share them with my friends the next day. When the show moved to CBS at 11:35 in 1993, it became a family affair and mom and dad watched it with me every night. The deeper I went into Letterman’s world, the funnier it got.

That was Letterman’s genius. He was bigger than life, the swaggering older brother who teased the world’s bullies. Night after night—6,028 of them in total—he created an unpredictable world populated with inside jokes and leftfield references that only regular viewers would understand. How could you explain the allure of Larry “Bud” Melman, the perennially mumbling elderly man who would walk on stage and shout at Letterman, to someone who had never seen him? How would you describe the genius of having stagehands Pat and Kenny read transcripts from The Oprah Winfrey Show with as little enthusiasm as possible, cigarettes dangling precariously from their lips? Rupert Jee, Biff Henderson, Mujibar and Sirajul—these were real people as well as characters on the show, and their place in Letterman’s universe wouldn’t make much sense on first viewing. You had to develop a relationship with them to fully appreciate them in context, and doing so felt more like participating in an ongoing conversation with friends than watching an entertainer every night. On the show’s best nights—and there were many of them—you felt like you were part of the joke.

That sort of time investment seems like an unreasonable request in an era of viral videos and diminished attention spans, and if you’re under 30 you likely have a hard time understanding exactly why both Jimmy Kimmel and Conan O’Brien respect Letterman so much that they instructed their viewers to watch his final episode instead of their own shows. Being old enough to remember Johnny Carson’s final Tonight Show in 1992, I can relate. Carson was welcoming and comforting in a grandfatherly kind of way, more an institution than a man. But I didn’t really get him—at least not like my parents did. By the early ‘90s, the tone of comedy had shifted sharply and Carson looked quaint, seemingly belonging more to the post-vaudeville world of Bob Hope and Milton Berle than the one of Seinfeld, The Simpsons, and, well, Letterman.

Today Letterman seems to occupy a similar position in the culture that Carson did 25 years ago. He’s universally revered by those who remember his prime years but mostly regarded with indifference by a generation raised by his comedic offspring. Though Letterman’s off-the-wall eccentricity and self-effacingly caustic demeanor accounts for much of his legend, he is neither as combative as Jon Stewart nor as goofy as Conan or Stephen Colbert. As Jimmy Fallon continues to remake the late night genre with unthreatening games of celebrity beer pong and high-fiving interviews, it appears that we’re entering an era where the persona-driven talk show is on the wane. Letterman was probably smart to retire—he was never going to be a good fit for the selfie generation.

Beyond all of this, it’s difficult for me to explain just why I feel such a sense of loss now that Letterman has retired. The Late Show has been pretty hit-or-miss for at least the last 10 years, and Letterman has lost much of his edge, seemingly never fully recovering from missing six weeks of shows in 2000 due to a quintuple bypass heart surgery. Since then, he has seemed disinterested, retaining much of his trademark silliness but lacking the focus or energy to stretch out the sort of running jokes or esoteric themes that would brilliantly and absurdly grow and mutate for weeks on end during his prime years. Maybe becoming a father at 56 softened him, granting him a serenity that undercut the insecurities that fueled his biting sense of humor. Maybe years of being trounced in the ratings by an astoundingly unfunny Jay Leno was more than he could bear. Whatever the case, more often than not he didn’t seem to be having much fun, and the sense of a man going through the motions was apparent. But even a half-invested Dave is better than no Dave at all, and I’m still not ready to say goodbye.

In truth, I probably never will be. Simply by virtue of being on our screens far more than any other TV personalities, late night hosts become part of our daily lives and routines. They’re the people we turn to when we want to shake off the anxieties of the day before slipping into bed, and we go through a changing world with them as one of the few constants. Ultimately, Letterman’s retirement isn’t just the end of our relationship with a man who formed much of the modern comedic vocabulary; it’s considerably deeper than that. Losing Dave is not just severing our connection to the world he created, to that wonderfully bizarre cast of characters, to our memories of fighting to keep our eyes open when we should have gone to bed. No, David Letterman’s retirement is nothing short of a reminder that no one can stop time and even the most reliable things in life will eventually end. You will get older, the world will move on, and no matter how great your escape it is only temporary. Good or bad, your alarm will still go off in a few hours and morning will still come. The only difference is that we now have one less place to flee from and revel in the absurdity of it all.