This post originally written in 2015 for now-defunct PopCulture/Lifestyle site Untied Magazine.
David Letterman took the stage of the Ed Sullivan theater last night for the final time. Not one for sentiment, Dave, always seeking the laugh, turned to his trademark disgruntledness, and opened by saying “I’ll be honest with you. It’s beginning to look like I’m not going to get the Tonight Show.”
It could’ve been possible that Letterman would only be remembered for following Carson on Late Night. Or for being passed over for the Tonight Show in the first shots of the infamous late night wars. But Letterman’s too good for that. He’s always been too good for that. His inventiveness and comedic pioneering is and was so profound that it’s almost impossible to tell anymore, because so many people have tried to emulate both his sardonic wit and anything-goes comedy style. The outpouring of love from other comedians and late night hosts (I wouldn’t call them peers, they’re far too young at this point) the last two weeks makes clear that he has had a profound impact on every young comedian of the last three decades. Letterman made The Late Show every bit the institution The Tonight Show once was. While he may not have always had the ratings to beat Leno or Fallon, celebrities knew he was the guy. He came out and made every night look effortless.
Letterman was no good at puff pieces or interviews that were just to promote the new thing. When people came on and that was all they were willing to do, Letterman’s disinterest was clear. That was one of the great things about him; he was incapable (or perhaps unwilling, for the sake of the show) of hiding his disdain or boredom. Sometimes those awful interviews became some of the best, like his chat with Justin Bieber, who he clearly had no patience for.
Googling awkward Letterman interviews uncovers a glorious treasure trove of stand-offish and biting back and forth.
But Letterman was also the best interviewer in late night. He could rescue a sinking celeb and turn their bombing story into comedy gold. When he had people like Tom Brokaw or Bill O’Reilly on he could talk politics and ask tough, probing questions. His interviews with O’Reilly–argumentative and serious– are so good as to be uncomfortable more than funny, but Letterman still finds time for jokes, mostly at his guest’s expense. He wasn’t a cheerleader, like Fallon, Leno, and many times even Conan, but he was able to guide guests to the most entertaining version of a chat all while making it look effortless. Conversations were natural, unpredictable. His non-sequiturs threw people off guard and made them bring their walls down. And while he could be acerbic to some guests, there were some he clearly loved having on the show. When that happened, there was the magic of genuine conversation that cut through the cluttered nonsense of the corporate PR-machine. Letterman was able to work in the realm of pop culture but not be co-opted or dictated by it. He used every moment to get a laugh, and the celebrities were just the most consistent tool to do that. He didn’t need comedy bits during interviews to make them funny, and when they happened they always seemed off the cuff and transitioned smoothly, rather than needing an introduction and setup.
Some of his interviews will probably be remembered for years to come. But it’s his inventiveness, his willingness to do anything for a laugh that will be his true legacy. It’s what made The Late Show with David Letterman what it was. Even as the late night scene grew and grew it was the only thing on TV like it. In more recent years, it was pretty clear that Letterman was growing restless and disinterested, which he admitted was part of the reason he’s retiring. But even in the midst of that he found ways to be hilarious in his satirical and ironic approach to the talk show format. He remained the most acerbic tongue on the talk show landscape, and the great wealth of his humor the last several years has been in that strength. Since announcing his retirement some of the energy clearly returned, his passion for showmanship was clear again, and he looked like he was having as much fun as ever.
Dave was also capable of being disarmingly honest and genuine. His speech following 9/11 about continuing on, or his return after his open heart surgery, or his interviews with political figures, and a Medal of Honor recipient all reveal a side of Letterman that was passionate, compassionate, and concerned. It’s hard to picture anyone else doing talk shows right now being able to provide that kind of pathos and speak to current political and social issues with such conviction, authority, or honesty.
At his very best, anything could happen on Letterman’s show. And usually it did. The trademark segment of his show might be the Top Ten list, but it’s hardly the most memorable (with thousands of hours, the hit-to-strike ratio is pretty high on those). The things I’ll remember best are recurring gags like WILL IT FLOAT? and THE OPRAH LOG, or what might have been my all time favorite, Know Your Cuts of Meat! And what will Christmas be without trying to knock the meatball off the tree? Or the Lone Ranger story? Or Darlene Love’s performance of Christmas (Baby Please Come Home)?
As a kid, Letterman may have been the funniest thing I had ever seen. Two particular comedy gags stand out to me: Letterman sending out Rupert Jee (who owns the deli around the corner from the Ed Sullivan theater. That’s it, he was just their neighbor) into the wilds of NYC and telling him what to do, and Letterman working at a Taco Bell drive through. Staying up late to watch Dave always felt so special, like I was being let in on some kind of amazing secret. His irreverence was always so clear, and that was made his comedy so disarming and genuine, even at its most ironic. I never got to see him live, but any time I took a trip to NYC and go to see that Letterman marquee was thrilling. That’s where the magic happened.
On his last show, Letterman made sure to thank his writing and production staff, saying that if there was anything the audience enjoyed about the show, it was more them than him. And while there is truth to that statement, there’s a reason Dave was the man on screen. His improvisational skills, his comedic timing, his willingness to go to any lengths for the laugh, were always clear. Just watch the Taco Bell clip above to see how quick he was on his feet. That ability to think on the fly is what made the rhythm of his joke delivery work so well, it’s what made his interviews the best on late night tv, it’s what made the remotes and the comedy bits and everything else work. Who else could have had the ideas and courage to take the show he was running and include his mom, or the guy who owns the deli around the corner? Who else would have the brilliant idea to send their mother out to cover the winter olympics?
If it was funny, he would go for it. When he would randomly burst into the punchlines from the show’s monologue throughout the episode (or the previous episode) and run them into the ground with Paul Shaffer, it was always in an attempt to fill a gap or relieve a dying joke. Letterman knew what he needed to do to keep the show moving. At the same time, he was never afraid of awkward pauses, sometimes relishing the extended silence to make the audience uncomfortable. All of that comes from a talent that is so subtle as to look like it’s no talent at all.
It’s pretty easy for me to say that a lot of my sense of humor comes from watching Letterman growing up. My fondness for bizarre,surreal, or non-humor is an obvious developmental influence. Dave’s leaving is very much the end of an era. He has become as much of an institution on television as his idol Johnny Carson, and with his stepping down the late night talk show format as it once was fades, too. Conan O’Brien is now the senior member of the late night talk show world, and with his relegation to basic cable, his potential for continued influence is pretty low, despite the fact that he remains goofy and entertaining. While I enjoy Fallon and Meyers and Conan and look forward to what Colbert will do, no one out there running these shows right now has the edge to be truly as subversive and as warmly biting as Letterman was. The celebrity PR machine needs someone willing to take the whole institution down a peg, and without Letterman, I hope there’s someone to fill that gap. It was one of his greatest gifts.
Of course, the greatest gift he gave us was his ability to put on a show every night and always make it entertaining, funny, and just slightly bizarre. Even when you didn’t watch, it was nice knowing that Dave was still there, still making people laugh.
Thanks David Letterman, for all the memories and all the laughs.
And now, a sneezing monkey.