The Last Days of David Letterman: Guests and Friends Remember the Major Moments From Late Night’s Leading Man

Late-night television is all about moments, and in 33 years (on two networks), David Letterman has created some unforgettable ones. We hit up his friends, frequent guests, and show staffers past and present for their favorites:

Paul Shaffer, Late Night and Late Show bandleader, 1982–present

“I had completed the first five years of Saturday Night Live as a pianist in the house band and then, the fifth season, as a featured player as well. Dave and his producer called me in for a meeting two years later and we hit it off. Dave mentioned that he had seen some of the things I had been involved with during Saturday Night Live, most notably when Billy Murray used to do his sleazy lounge act. Then Dave said, ‘What kind of band would you have? And by the way, you can only have four pieces.’ I think Johnny Carson didn’t want Dave to have a big band, because he had a big band. So I said, ‘I picture this as a late-night R&B group playing instrumental versions of the songs we love in the style of Motown, Stax, and the great soul and R&B of our youth.’ Dave said, ‘Well, I always thought of myself as the Wayne Cochran of comedy, so it’s perfect.’ I said, ‘I’ve got to work with this man.'”

Billy Crystal, actor, comedian

“Some people are just born for a job. That’s Dave. When he was born and the doctor slapped him, he went, ‘Well, good evening, ladies and gentlemen.’ I had a dinner last year with Dave, Marty Short, Steve Martin, and our wives. It was fantastic, and he looked like he loved being out. It was silly great. Steve likes to barb him, and it’s particularly funny. I do it on the air. I’ll call him on stuff. I love making him laugh. Robin [Williams] and I felt the same way. As soon as we finished, we would call each other as we were leaving the studio or sometimes from the dressing room. ‘How’d it go? Are you done? Did he laugh? Was it good?'”

Jimmie Walker, actor, comedian

“I met Dave at the Comedy Store [a club in Los Angeles]. For some reason, we just clicked. He was on my [stand-up writing] staff for seven, eight years, coinciding with Jay Leno, Louie Anderson, Byron Allen, and all those guys. He and Leno, a lot of people don’t realize, they were the best of friends. Dave idolized Leno. That may have caused a lot of what went on [when Leno got the Tonight Show job]. He fought for Leno at every turn. At that time, Leno was considered the best comic, and he couldn’t get on Carson, which was a big deal. Carson was a huge fan of Letterman’s, so Dave had his ear. When Carson didn’t want to use Leno, the guy who went and fought for him was Letterman.”

Jack Hanna, zoologist

One of Letterman’s favorite guests, the director emeritus of the Columbus Zoo has appeared over 100 times. “In 1987 or ’88, my buddy who’s a director of a Louisiana zoo had me bring what he called the biggest beaver in the world to the show. I put it in a plastic swimming pool, and he takes a crap, starts flapping his tail all over, and everybody’s laughing. I grab the beaver by the tail, and I don’t know if Paul Shaffer hit a note or something, but the beaver bit me. The tooth went all the way up between my thumb and first finger, hit that main vessel. I have three minutes to get to my next animal, electric eels. Blood was spurting. My face was perspiring. I was in a state of shock but was not going to quit. I walk back out there, and Dave did not know anything about it. All of a sudden, blood started flowing out the top of my glove onto his desk. He says, ‘Oh my God, call an ambulance.’ I go to the hospital, then fly back to Columbus for surgery. I have no feeling in my thumb to this day. The next time I was on the show, Dave says, ‘Jack, I hope you learned your lesson last time: Don’t ever mess with another man’s beaver.'”

Will Forte, Late Show writer, 1997–1998

The future Saturday Night Live and The Last Man on Earth star did a brief stint on Letterman’s writing staff. “At the end of my first week, they were doing a remote segment called ‘Everything Gets Funnier When Someone Gets Hurt.’ As part of the segment, I’m supposed to stab Dave’s hand with a pair of scissors. It was a pair of real scissors, and I was super nervous and terrified I was accidentally going to stab him. In the clip, they cut away to a shot of a fake hand and the scissors going in. So I needed to at least make it seem like I was coming close to his hand. I don’t know why they didn’t use rubber scissors, but they used real ones, trusting that I could stop before his hand. Fortunately, it worked. But that was the way I met one of my all-time comedy heroes.”

Al Chez, trumpet player, 1997–2012

“Dave was a huge Warren Zevon fan, and when Paul called in sick or didn’t come in for a holiday, Warren was always his sub. By 2002, Warren was dying [of cancer]. He had asbestos in his lungs. For his last public performance on October 30, 2002, he was the only guest we had on the show for a whole night. All he did was talk to Dave and sing songs. After that performance, he went up to Letterman’s dressing room and was like, ‘Thank you for the support. Thank you for getting me in the public eye and for being a fan.’ And he gave David his guitar that he used his whole career and basically said, ‘I’m not going to need this anymore, and I want you to have it.’ It left Letterman totally in tears.”

Amy Sedaris, comedian, author, actress

The Strangers With Candy star has been a guest more than 30 times. “[The question always was:] Is he going to talk to you during the commercial break? Sometimes he’s in the mood to talk to you during the break and sometimes not. Sometimes he’ll ask you a question, like, ‘Oh, have you ever done heroin before?’ He’ll trip you up to be funny. I remember the first time I was on, I was doing a play, Wonder of the World, and he said, ‘Do you ever get tired of doing the play eight times a week?’ And I was like, ‘Not really, because I just started doing it.’ And he said, ‘Oh, I got tired of doing this show after the first six weeks.’ Then it was, ‘And we’re back.…'”

Jerry Foley, director, technical director, producer, 1990–present

“Remember the Chilean miners who had been buried underground for so long? Our talent department booked the guy [Edison Peña] who was jogging while they were trapped underground. He was also very much into Elvis. He had an interpreter and a PR person with him, and they were very emphatic that the guy was traumatized by this experience and if the questions became too graphic about him being entombed underground, the guy could actually freeze up. We had him on for three segments, and Dave started out gently, well aware of how difficult the situation could become. He gradually won this guy over, gained his trust. By the third segment, Peña jumped to his feet and did an Elvis impersonation. Then Dave wound up hugging him. It was one of the most skillful things I’ve seen any journalist or talk-show host do at a desk.”

Regis Philbin, TV host

The TV icon was an occasional guest host and appeared more than 150 times on Letterman’s show. “I had a heart condition, and they wanted me to get bypass surgery, so I called him because he had just been through it a few years before. He just took over. He got me the best doctors, he picked out the hospital room I was supposed to be in, he took over the whole thing. But the night before the surgery, I couldn’t sleep, so I turned on his show and heard him say, ‘Tomorrow morning, Regis is going in for surgery, and they’re going to bust him open like a lobster!’ That’s all I had to hear. I couldn’t sleep the rest of the night. I was terrified.”

Marv Albert, sportscaster

“When Dave started out at NBC, I was doing the 6 o’clock and 11 o’clock news on Channel 4 in New York, so I was always available. I was once referred to as the ’emergency backup guest,’ which was true. As a result, I’ve made a lot of appearances [125 in total], as a regular guest or in a number of comedy bits. When you’re on, you’re kind of in Dave’s universe and you roll with it. It’s a wonderful make-believe world. I rode in on a horse once. I was just fearful I was going to fall off the horse. Another thing we used to do was ‘Elevator Races.’ We’d be in 30 Rock and they’d put people in the elevators and race them. I would announce the play-by-play, along with Bob Costas. People in the lobby had no idea what was going on.”

Cher, actress, singer

In 1987, Cher and her ex-husband Sonny Bono did an impromptu duet of their hit “I Got You Babe.” “That was not so nice, because they blindsided me on that, both of them. I wasn’t happy. I didn’t want to sing that song on his show, because it was too emotional. Sonny and I were trying to maintain a friendship [at the time] and I felt it was too personal. I knew that it was a very tender thing for Sonny, too. It was a display of emotions that I didn’t want to push him through, because I knew I’d be able to go through it easier. But I forgave them.”

Dr. Phil McGraw, psychologist/TV host

“Dave was doing this series called ‘Words of Wisdom From Dr. Phil.’ He was dogging my ass pretty good. They would take things I’d said and splice them together. They were really mocking me, but it was never mean-spirited. The first time I went on, it was definitely tension-filled. I had a list in my pocket of names he had called me: quack, half-baked quack, guy that approves your check at the grocery store. I pulled the list out, and he was squirming. I read those off, and he just died laughing. I called him out, he admitted it, and we went back and forth about it. But he could not have been nicer and more gracious.”

Alan Kalter, announcer, 1995–present

“We do a thing I call ‘How Alan Can Make You Happy.’ Dave says, ‘Alan, you want to say something?’ I pick some celebrity who has been in the news, and I turn to a camera to talk directly to that person. The lights dim, Paul plays sexy music, and I speak to someone who, for example, has just separated from her man. I let her know that I’m available to make that night the best of her life. I’m relying on the cue cards, and it always goes right, because all I have to do is read. One night, the lights go out on my card. I’m squinting, making up words, trying to remember what I would like to say to this person, what I’ve read before. I think I’ve been somewhat successful and maybe the home audience won’t be able to tell. I finish, figuring Dave’s now going to go to the next thing. He looks at me and goes, ‘Trouble reading the cards, Alan?’ [Laughs] He’s very spontaneous. When something goes right, it’s great. When something goes wrong, it’s even better. That’s what makes comedy.”