Paying Tribute To David Letterman: The UPROXX Staff’s Favorite Moments

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There is no real difference between being a sports fan and being a comedy nerd, save for the solitary method of appreciating the former and the wide social acceptance of the latter. Yes, they’re exactly the same with the same penchant for strong opinions and abundant passion — which is why David Letterman‘s retirement feels like Michael Jordan’s first and second retirement and Derek Jeter’s last game. Only it’s more impactful because of the many ways that Letterman altered his “sport.” If football had been played on a 50-yard field with a limit on how many points a team can score in one game before one gap-toothed man made the field bigger and trashed those restrictive rules purely with the way he played the game, then we’d be talking about a one for one comparison, but that kind of thing doesn’t happen in sports. That kind of sweeping change doesn’t happen anywhere, but it happened in comedy thanks to David Letterman. And that’s why grown men are crying and why the world is taking notice.

Over the last few days, we’ve cut up David Letterman’s 33-year career into slices, serving up his achievements to our readers for their enjoyment while also stirring memories of our own personal connection to his career. So, just hours away from Letterman’s final episode, it seemed right to share those favorite moments with you, and we do hope that you share yours with us in the comment section.

Before we get to the group, though, I’d like to start with my own favorite moment even though I could list about 100 of them. But in the interest of not doing that, how about we start at the very beginning with Calvert DeForest (aka Larry “Bud” Melman) paying tribute to Frankenstein and Letterman.

These are the first words that came from Late Night with David Letterman:

“We are about to unfold a show featuring David Letterman. A man of science who sought to create a show after his own image without reckoning upon God. It’s one of the strangest tales ever told. I think it will thrill you, it may shock you. It might even horrify you. So if any of you feel that you don’t care to subject your nerves to such a strain… well… we warned you.”

Truer words have never been spoken. Weirdness and originality had found a home on late night television and you’re damn right it thrilled us.

Andrew Husband

Nothing beats Letterman’s interview with O’Brien in 2012, nearly two years after the latter was famously booted off The Tonight Show in favor of previous host Jay Leno’s return. Why’s it so good? Because you’ve got two late night comedic geniuses coming together with one goal in mind — making fun of Leno. Or, as Letterman puts it, “I think the longer we just sit here, the more uncomfortable it will make Jay.”

Andrew Roberts 

If I had to pick a favorite moment from across David Letterman’s career, I’d probably have to go with Crispin Glover. I know it’s not from his CBS era, but Glover represents some of the oddest interviews I’ve seen and they’re arguably my favorite parts of Letterman’s career. Yes, he almost got kicked in the head during Glover’s first appearance and then spent two almost equally odd interviews trying to find out why. What stands out is the mystery surrounding it all. Is it an Andy Kaufman-inspired prank gone wrong? Is Glover actually high as a kite? How close did that kick actually come to hitting Letterman in the head? We’ll probably never know.


Having a grandfather who was a war hero, I was drawn to John McCain during the 2008 elections, so much that I was that guy on Facebook*. But once he secured the Republican Party’s nomination, he changed. And it wasn’t just that he was more professional in delivering the standard talking points… He was completely different. I was angry at the world that this man who had been so funny and self-aware on The Daily Show, and made me think there was hope for a little more common sense in Washington D.C., was suddenly a typical politician.

Watching this episode was surreal and fascinating. It was just impossible to believe that someone in a position of power like McCain could have his people flat-out lie to the second most important man in late night TV at the time, and think no one would notice him appearing on CBS News at the very same time. What always set Letterman apart from Leno was that “don’t give a f*ck” attitude,” and this was Dave taking on a man who could possibly be the next president. And he wasn’t just taking him on, he was going all in. Watch this once, twice or 437 times. It never gets old.

*I have since dedicated my life to making fun of such people, and I hope that in time the world can forgive me for being a dumbass.

Bennett Hawkins

One of my favorite things about the Late Show with David Letterman was its commitment to tradition, no matter how silly those traditions were. Dave would attempt to guess his mother’s Thanksgiving pies, Darlene Love stopped by to belt out “Baby Please Come Home for Christmas” and Jay Thomas tried to knock a meatball off the top of a Christmas tree. The traditions were rather bizarre, but Letterman continued to roll them out year after year, probably for his own amusement as much as his fans’.

One of those traditions was Letterman calling upon his longtime bandleader Paul Shaffer to tell the story of Cher singing “O Holy Night” on a 1973 Christmas special. He’s been doing it since at least the early 1990s — probably longer – and as Dave routinely pointed out, the biggest laugh always came with the word “muff.”

The holidays just won’t be the same without it.

Ben Goldstein 

I don’t know why Chris Elliott never became a huge star, but if I had to guess, I’d say it’s because he’s weird looking and makes most people uncomfortable. Nevertheless, Elliott’s numerous appearances on Late Night with David Letterman helped define that show’s oddball sensibility in the 1980s. For me, two Chris Elliott segments immediately come to mind: 1) His hilariously unflattering impression of Jay Leno (above), complete with hideous prosthetic chin, and 2) his gross/brilliant dog food taste-testing bit. Both appearances proved that Elliott would go places other comedians wouldn’t in pursuit of the laugh. Whenever he was on the show, he was the best part of it.

I’d be surprised if Elliott wasn’t featured on Letterman’s final show in some way, although it would be hard to top the tribute that he gave Dave back in February, where he got choked up discussing what David Letterman has meant to his life. For once, the eternal goofball reveals a moment of true heartfelt emotion, and speaks for everyone who isn’t ready to let Letterman go. And then he sings, and it’s wonderful.

Stacey Ritzen

Back in September of 2007, at the height of Paris Hilton mania, the perpetually baby-talking Paris Hilton appeared on the Late Show to promote her new line of perfume and a movie. However at the time the socialite had only just recently been released from jail, where she had spent 45 days on a probation violation. Dave wasn’t so much into talking about the perfume and stuff, and instead grilled Hilton, asking her detailed questions about her time behind bars.

Hilton politely answered his questions for a few minutes and then charismatically said that she had “moved on with her life and didn’t want to talk about it anymore,” to which Dave responded, “This is where you and I are different, because this is all I want to talk about.” He was relentless, and continued way beyond the point that Hilton got visibly upset. It probably crossed the line of “funny ha ha” to “funny mean,” but this was also Paris Hilton we’re talking about here.

Paris and Dave have since made up and she’s appeared on his show several times since. It’s just a shame he never brought the knives out like that for Kim Kardashian.

Dustin Rowles

People don’t often remember this, but back in the day — especially when he was still on Late Night — Letterman would frequently leave the studio to do remote segments, pieces that would probably dominate YouTube if that had existed back then. He gradually phased out those segments once he moved to The Late Show at 11:30, although he did continue to do remotes with various people from the neighborhood (Rupert Gee, chief among them). Maybe my favorite remote segment in the early days of The Late Show, however, was when Dave ran the drive-thru for a Taco Bell (he’s also worked the McDonald’s drive-thru and harassed the drive-thru workers at the Wendy’s drive-thru). The Taco Bell drive-thru segment, however, was vintage early Dave, playing a wise-ass who’d harass the drive-thru customers to their breaking point, rarely giving viewers at home the satisfaction of the reveal.

Danger Guerrero

It’s not so much that he flung things off a roof just to watch them explode all over the ground below. I mean, don’t get me wrong, it is that too, to a degree, as throwing stuff off a roof is great fun. One time in college my friends and I spent a whole afternoon doing it. Highly recommended. But the reason I’m including it here is just the sheer chaos of it. A broadcast network gave David Letterman a late-night talk show and he responded by splattering watermelons and televisions and such, among his many other unhinged stunts. It was anarchy. Sweet, sweet anarchy.