TIME Television

9 Late Show Guests Remember Their Favorite David Letterman Moments

From Regis Philbin to Emmylou Harris, former guests recall their fondest memories with Dave

After almost 15 years as host of Late Show and more than 30 years as a late-night TV host across two networks, David Letterman is signing off for the last time on Wednesday night.

Here’s a look back at some of the favorite moments from guests of Dave.

Betty White

“When you’re doing the David Letterman show, you always get a call ahead where the segment producer asks you some questions and takes notes to pass on to David for the interview. I’ve done the show innumerable times and we’re yet to use any of the notes—we love each other and we just take off. What fun. I will miss him so. But look out—I’ll find him!”

Regis Philbin

“One year Dave surprised me on my birthday with a beautiful red Vespa motorbike. It was parked in front of the studio and he wanted me to go out, jump on the Vespa and ride it down the street. I didn’t get very far. In fact, I fell off and almost killed myself. They took a shot of Dave, who had thrown his hands up to his face saying, ‘My God, what have I done!’ I think he really got scared for a minute and didn’t think I was going to get up.”

Mayor Rudy Giuliani

Giuliani Letterman
Joe Tabacca—APDavid Letterman greets New York City Mayor Rudolph Giuliani as he helps fill a large pothole on 53rd Street outside the Ed Sullivan Theater during a taping of the Late Show With David Letterman on July 26, 1994 in New York.

“When I was mayor, one night David was complaining very bitterly about a pothole that was out in front of the theater on a side street where the audience waits for people to come out. It was gigantic—he showed a picture of it, and he challenged me or the city to have it fixed. So I got a crew together, we came that night, and we showed him how we fix a pothole in New York. That may have been the first and last pothole I filled in my life.”

Mike Mills, R.E.M.

“The first time we played Letterman, Peter and I had smuggled some beer into the dressing room and Dave stopped by to say hi. He saw the beer, and he said, ‘Are you guys nervous?’ Peter and I said, ‘Yeah, a little bit.’ He said, ‘Well, don’t worry, it’s not like it’s a real show or anything.’ We laughed and felt better. He put us at ease and we had a great time. That was our first national TV show ever, so it was very exciting.”

“Jungle” Jack Hanna

“Dave Letterman is the most quick-witted person I’ve ever worked with. One time I brought a lion on the show and he asked, ‘Hey Jack, where’s that nice lion from?’ I said, ‘The Columbus Zoo, Dave.’ I was being serious. He said, ‘No, where’s it from?’ ‘I just told you, Dave.’ ‘You think I don’t know it’s from Africa?’ Another time I had a two-toed sloth, and I told him it’s like a three-toed sloth, but a little bigger. He said, ‘But what’s the difference?’ I said, ‘Look, one toe—I just told you!’ Animals weren’t his thing, really, until I did the show. But today, he’s a conservationist—he probably does know more about animals than I do today. I cannot thank him enough for what he’s done for the animal world.”

Dan Rather

“Looking back, this was probably ill advised. But I grew up in the oil fields in Texas, and I’d been chewing tobacco since I was 14 years old. It’s a gross habit. I’m happy to say I no longer do it. At any rate, somebody on David’s staff said, ‘We know you chew tobacco, and Dave would be interested in learning how.’ I had some reservations about this, and CBS, when they heard about it, said, ‘Absolutely not.’ But nonetheless, when I got there, I had a pouch of Red Man chewing tobacco. I attempted to teach him, but before I could say anything, he swallowed it and he turned emerald green, right on camera. That pretty much ended the segment, and—as far as I could determine—it ended his interest in chewing tobacco forever.”

Paul Shaffer

“Warren Zevon was a wonderful singer/songwriter who in the ‘70s made quite a mark with his contribution to the California sound. He appeared on Late Show several times and, when I needed to take time off, he became my regular sub. Then he got cancer, and he appeared on the show one last time—everyone around him knew that he was terminal. He performed three songs with me and my band for old times’ sake. Dave Letterman devoted the entire show to him, and on the panel, he asked Warren, ‘In your position, is there anything you know about life that you could impart to us?’ Warren smiled and he said, ‘Well, not unless I know that you’ve got to enjoy every sandwich.’ To me, that’s a great legacy right there. It was a real life experience for all of us.”

Jay Thomas

“I had told this story about the Lone Ranger to some comics over dinner once, and one of them told some other comics. Dave heard about it, and on the air, he said, ‘I hear you tell one of the funniest stories ever.’ I was not warned, and I didn’t know if it was going to get a laugh—I had never tried it out. But the building almost collapsed, the laughter was so big, and Dave falls back in his chair laughing. He pulls forward, and the king of late night television says, ‘That is the greatest talk show story I have ever heard.’ I was self-actualized. For 20 years each Christmas, before I re-told the story, he would say, ‘Jay is going to tell the greatest talk show story ever heard.’ He literally immortalized me that evening.”

Emmylou Harris

“I did the Late Show a lot. Dave was very supportive of every aspect over the years of everything I’ve done—different bands, different projects. Gillian Welch, Sheryl Crow and I came on right after 9/11, and it was a totally different, serious thing. The show must go on, but everybody was feeling the tragedy. We were able to do a beautiful gospel song a capella called ‘Bright Morning Stars,’ and I think we did ‘Will the Circle Be Unbroken?’ which was probably Dave’s idea—I think that’s a very special song to him. We’re gonna miss him! It’s kind of hard to imagine evenings without Dave.”

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