Andy Daly Tells Us About The First (And Only) Time He Appeared On Letterman

Before comedian and actor Andy Daly wore his khaki ensemble on Review, he sported a similar look during his first (and only) appearance on the Late Show with David Letterman on January 16, 1998. With less than a week to go before Letterman’s final episode on May 20, Daly uploaded the bit to YouTube on Thursday night and wrote about the experience on his official website.

The sketch, written by Late Show writers Rodney Rothman and Justin Stangel, was a part of one of Letterman’s many iconic running gags — the “CBS Mailbag.” Daly played Carsen Donn, a Denver man who wanted to propose to his girlfriend of five years on national television. This being a Letterman sketch, the proposal didn’t necessarily go according to plan.

Daly was nice enough to chat with us about the sketch and how it came about, as well as his longtime fandom for all things Letterman. We even got him to spoil the ongoing #FindForrest campaign for Review‘s second season on Comedy Central.

You had done bits on Late Night with Conan O’Brien around the same time. How did Letterman come about?

When I first moved to New York, I got involved with a company called “Chicago City Limits” doing short-form improv, and some of those people were doing a sketch comedy show down in the West Village organized by Justin and Eric Stangel. There was another guy in that orbit named Rodney Rothman, and Rodney got hired onto Letterman as a writer. Then Justin and Eric got hired onto Letterman as writers. Rodney eventually became head writer and has gone on to all kinds of things, and the Stangel brothers were head writers for years. I think they’re still affiliated with the show in some way. I’d known both of those guys, so a few months after the Stangel brothers got there, I got a call that Rodney and Justin had collaborated on this viewer mail bit that they wanted me to do. That’s how that came about.

Did this Letterman bit come before or after Conan?

I had done a few things on Conan. As a matter of fact, I had said that I would do a Conan bit that day, the same day as Letterman. And I had to call Conan’s cast director and say, “Hey, listen. I have a chance to work with David Letterman! I gotta do it.” They were understanding.

When you came on board, were you involved in the writing process or were you just there to act out the bit?

No, I was just there to act out the bit, but I am responsible for that one line in it. The way that happened was, I got there to rehearse, and because the bit starts with me in the wings and ends with me in the wings, the way we rehearsed it — nobody introduced me to Dave or anything, there was no chit chat with Dave — we just started the rehearsal with me in the wings. We came out, we did all the lines. He ad-libbed the line when the phone rings and I say, “Oh that must be her,” and Dave goes, “Does she have that number?” That was his ad-lib, and everybody laughed because it was commenting on the ridiculousness of the premise.

At the end of the rehearsal, I run into the wings as scripted and that’s it for my interaction with Dave. In between that rehearsal and the taping I thought, “If he says that line again in the taping, I should have an answer. He’s asking me a question so I should have an answer.” So I came up with the answer, “All my friends have it.” I thought of running it by the Stangels and Rothman, but I was afraid somebody would say, “Don’t do it.” And I was like, “Fuck it! I want to play.” That was the extent to which I was involved in the writing. I came up with a line, didn’t tell anybody about it, and just said it when we were taping.

It goes over really well. Dave and the audience laugh at it.

Oh really? Well that’s funny because I remember thinking at the time that Dave was maybe not happy. He shoots a look out, and I’m not sure whether he’s looking out at the audience or looking at his producer. I was afraid there was a moment of him looking out at the producer like, “What the f*ck did this kid just do?” And the way he puts the phone down in front of me, at the moment felt a little bit like he was slamming it down. I remember in the moment thinking, “I’m not sure that went over great with Dave.” Maybe I was just hypersensitive at that moment.

Did you ever work on Letterman again?

I’ll tell you the story. When it was over, I was so excited. I was so amped up about it that I couldn’t leave the building. I was going around saying goodbye to makeup, hair, wardrobe, the band — it was like the last day of summer camp for me because I was just so unbelievably excited. I hung around in the building so long that when I finally left out the stage door, Dave was leaving too. So he’s walking down the stairs, and we’re coming face to face with each other, and I looked at him like, “Oh my God, we’re going to have a moment!” He hadn’t said a word to me that wasn’t part of the bit previously.

So he’s says to me in the flattest monotone that the human voice can accomplish, “Nice job. Come back some time.” My stupid response to that, because I’m so fucking cocky and amped up at that point, was “Oh, I intend to!” By which I think I meant I was going to be in that chair promoting movies and whatever. I don’t know, it just seems to me like I was on a rocket to the stars after that exciting Letterman appearance. He didn’t say anything to that. He just walked out. That was 17 years ago and I’ve never been back. It’s kind of too late.

The optimist in me wants to assume that most people watching Letterman know that, unless specified, it’s not live. So when a bit like this happens, with a live marriage proposal and phone call, most people will know it isn’t actually real. But you’re so committed to it, I want to know what she’s says.

Prior to doing that bit, I never knew that any of the “CBS Mailbag” stuff was phony. You know what I mean? And I guess I still don’t know if that was an actual letter that he received or not, but I think it probably wasn’t. I think that the letter itself was fake to cue up that sketch. But yes, thank you. I knew that at the point when the phone rings, anybody who’s critically thinking about this is going to realize, “Oh, well none of this is real.” But I tried to, at least up until that point, make people think that this is an actual marriage proposal. Looking at it now, I don’t think it’s actually all that convincing, but at the time I thought I was being pretty convincing. I think that I actually look at little too comfortable on camera. If I could do it again, I’d make myself look less comfortable.

That could be an audience submission for another season of Review.

I should pitch it to the Letterman show on their last week. “Look, let me come back. I have some ideas on it. I think I could do a better job on the bit. Let’s do this again. I have some notes from myself.”

Three episodes left. We can do this!

We can do this. C’mon, Uproxx!

Were you always a fan of Letterman?

I think I discovered Letterman through one of his prime time specials on NBC, and I started watching him religiously in 1987 when I was a high school sophomore. I stayed up until 1:35 in the morning every week day throughout high school to watch his show. And I had to watch until the end, because sometimes he would end the show saying, “I’d like to thank most of my guests tonight.” There was one night when I swear he ended the show by calling out an NBC executive by name, “I’d like to thank so-and-so for ruining my day, my show, and my entire weekend.” There was no explanation for the audience. You had to watch until the end because crazy shit happened in the final moments of that show.

I was a Letterman super fan and, as a matter of fact, I was not a good student in high school — probably because I was staying up to watch Letterman every night. All of my friends were talking about going to college, and I had no interest in it. It sounded crazy to me to do four more years of school. When I read an unauthorized biography of David Letterman, I learned that he went to college to study communications, television and radio broadcasting, and I thought, “Oh, OK. It’s cool to go to college and acquire some expertise in an area of your interest. Okay, I can imagine doing that.” That’s how I ended up at Ithaca College, because they have a great communications department. So literally, Dave Letterman is the reason I went to college.

The second season of Review is coming up this summer. Will we in fact #FindForrest?

Well that’s sort of a spoiler for our digital campaign, but yeah sure I’ll go ahead and spoil it: There’s a good chance Forrest is going to get found. It would be pretty hard to edit around him at this point.

I’m enjoying the campaign. A lot of people were posting news snippets from cocaine drug busts, saying “We found him!”

It’s so good. I clicked on the hashtag #FindForrest and I’m laughing a lot. People are really getting into it. I love it.

We’re eagerly awaiting the second season.

I believe we did a very good job in season two of making a show that people who liked it in season one are going to really appreciate what we did. But also, people who are just finding it will also enjoy it. I think we threaded that needle pretty well. At least I hope so.

The second season of “Review” premieres this summer on Comedy Central. The last episode of the “Late Show with David Letterman” airs on CBS on Wednesday, May 20.

(This interview was edited and condensed.)