An Oral History of Madonna’s Infamous 1994 David Letterman Appearance

It’s difficult to put into context for those who weren’t there just how big of a star David Letterman was in March of 1994. He had just left NBC nine months earlier—where he’d reigned tall at 12:30 AM for 11 years—to move up to 11:30 PM at CBS as host of The Late Show. This was a franchise created especially for him, and it made him the highest paid host in late-night history. He was at the height of his powers as a broadcaster, and at this point was number one in the ratings against Jay Leno’s Tonight Show. Being a guest on his show was a rite of passage, much as it had been when Johnny Carson hosted The Tonight Show. If you were sitting opposite David Letterman, you knew you had made it to the big time.

If Letterman was the biggest thing on TV, Madonna was the biggest thing in popular culture. You’d be hard pressed to find someone who was more successful than Madonna, frankly because there was no one. If she was doing something, you couldn’t help but watch.

The mere notion of Madonna going on any talk show was rare. She didn’t need the publicity. The relentless tabloids took care of that for her. Nor did she have anything to promote. Someone of her magnitude would seldom go on without a reason. But on March 31^st, 1994, she did it anyway. She went on David Letterman’s Late Show for her first visit with the host in 6 years. Everybody would be tuning in no matter what. But what we got was something so bizarre that we cannot help but marvel that it was ever really a thing 30 years later.

To be sure, this was not your average television interview. Not that anything with Madonna was ever “average,” but this seemed to be in an entirely different ballpark, even by her standards. From starting the interview by asking Letterman to sniff the pair of panties that she’d gifted him, to calling him out on “going soft,” to cursing more than a dozen times and finally refusing to leave, it was a spectacle that was going to be talked about and analyzed. Madonna—who was never not in control—would later claim that this was her way of taking on censorship and the taboos of what was acceptable on television. If that was her goal, she certainly accomplished it.

To commemorate the 30^th anniversary of this fascinating chapter in late-night history, we spoke with several key Letterman staffers who saw the threads unravel before their very eyes: Then-Executive Producer Robert “Morty” Morton, Segment Producer Daniel Kellison, Head Writer Rob Burnett, and Writer Jon Beckerman.

DANIEL KELLISON (SEGMENT PRODUCER): I don’t think Madonna had done the show since [ she made a surprise appearance in 1987 ] with Sandra Bernhard. She had come on and caused a mini stir back then by alluding to the fact that they hung out at the Cubby Hole, which was a lesbian bar in the west village. That generated some headlines. But we never really heard from her again after that.

ROBERT MORTON (EXECUTIVE PRODUCER): She was Taylor Swift. She was the one everyone wanted on their show. There were very few people in those days that spiked ratings and she was one of them. 

KELLISON: She had been involved with a lot of actors like Sean Penn and Warren Beatty and Dennis Rodman and Charles Barkley, and Tupac, who she was going out with at the time. So, she was giving Letterman material [in his monologue] every single night. And Letterman was relentless, I would say. It was just something that was a gift that kept giving. Madonna was in the press every day. 

After years of asking, the call finally came in from Madonna’s publicist, Liz Rosenberg. For the first time in 6 years, she was willing to go on Letterman’s show.

ROB BURNETT (HEAD WRITER): The show was at the height of its popularity. It was so popular that even I would get recognized when I went out in New York City. Add Madonna to that mix and you knew going in that a ton of people would be watching that night.

KELLISON: She agreed to do a pre-interview. She wanted to give it back to Dave and make him squirm a little bit. So, we had an idea, which is basically that Madonna would come on and complain that he’d been taking shots at her. And he’d say “It’s all exaggerated. I love you.” She would say “I brought some tape from the show.” Then she would playback three of jokes that Letterman made about her and have him sort of explain himself. That was the premise. She seemed to like the idea a lot. I told Letterman that I thought everything had gone very well. I was looking forward to it and I thought we had nothing to worry about.

MORTON: We were excited about having her. There was always a certain amount of mischievousness when she came on. Even though they were close in age, Letterman was the guy in the suit and tie and was Mr. Establishment. She was looking to ruffle his feathers. And that always made for great television.

KELLISON: The day of the show, she showed up and I think the only person with her was this guy Kevyn Aucoin, who was her makeup artist. I knocked on the door and said “Hi I’m Daniel.” She didn’t get up or offer her hand. Instead, she said “Suck my dick.” I was like “What? Sorry?” Then she said it slower. “Suck my dick.” She and Kevin were laughing hysterically. And I was like “Oh shit. This is not good.” I said “Okay, well let’s just power through and get through it. Like we discussed, there’s going to be three pieces of video tape.”

And she stopped me and said, “That’s way too much for me to remember.” I went “It’s not really that much. It’s kind of super simple. You show a tape, you get his reaction. You show another, you get his reaction. There’s three.” She says “Yeah, I’m not going to remember all that.” I ask her why and she started laughing and giggling and went “We smoked a little endo before we came here.”

The term “endo,” slang for marijuana, had recently been popularized by Snoop Dogg in his song “Gin and Juice.”

BURNETT: I remember that she came right out of the gate with an agenda––to be rebellious and edgy. Generally, when guests come out with their own pre-plan and don’t include us and Dave, it doesn’t go well. (See: Crispin Glover.) Our segment producers were the very best in all of late night and could guide and help almost any guest succeed. They were wizards, truly. Not to mention Dave, who will also help, if he knows what you are up to.

KELLISON: I would never go to Dave’s dressing room. But in this moment, I did. I just gave him a heads up. “I don’t think this is going to go well. I’m a little bit anxious. She might be stoned. I’m not sure what’s going on. I don’t have the same feeling I had when we were on the phone.” I don’t remember him saying much of anything. He was nodding his head and that was it.

The writing was on the wall. There was really nothing they could do to stop it, as the train was leaving the station. Letterman’s intro for Madonna––which Kellison had written––probably didn’t help matters. “My first guest tonight is one of the biggest stars in the world. In the past few years, she sold over 80 million albums, starred in countless films, and slept with some of the biggest names in the entertainment industry.” 

Madonna walked out, her hair black and slicked back. Letterman started by jokingly encouraging her to kiss a fan in the audience. She wasted no time firing back “Why are you so concerned with my sex life?”. A minute in, she turned to Letterman and said “Incidentally, you are a sick fuck.” This was “f-bomb” one of fourteen. Immediately after, she revealed to the audience that she had given Letterman a pair of her underwear and encouraged him to smell them. Less than 2 minutes after the train had left the station, Letterman was doing whatever he could to try to keep it from going off the tracks entirely.

KELLISON: She came out prepared to pick a fight. Dave kind of had this rule about keeping it above the belt. And he kind of really believed that, but this was not an above the belt interview. 

BURNETT: Madonna wanted to be combative. She started using the “F” word, which at the time seemed like a bigger deal than maybe it would now. I was in my normal spot in the theater to Dave’s left and near the audience, and I could hear the audience have several reactions at once. They “oohed” and “ahhed” of course, but also there was a feeling of genuine nervousness in the room.

MORTON: That whole room had a tension that you could cut with a knife. That whole theater was laughing, but it’s kind of cringe. So, I’m there right at the foot of the stage cringing, the whole audience behind me is cringing. I assume everyone in the control room was cringing, too. 

JON BECKERMAN (WRITER): I think the way it was received within the building was less a thing of “Oh, this is fantastic. We’re going to be getting so much attention for this. This is great.” It was more like “Oh, this is unseemly kind of. I’m not so sure this is a nice thing.”

MORTON: At heart, [Letterman] was a very traditional broadcaster who came up in traditional broadcasting, with traditional broadcast standards. It was always so funny when the network would say “Dave can’t say this. Dave can’t say that.” And it’d be like “Do you know what kind of performer Dave is?”

BECKERMAN: If you look at Dave’s comedy at the time and over the course of his career, there’s not a lot of shock involved. It was never something that he warmed to, really. There was not a lot of foul language. There was not a lot of sexy stuff. That kind of comedy I think was disdained a bit at the show.

BURNETT: Dave was immediately uncomfortable and unhappy. Dave always took to heart that he was hosting a show on “The Tiffany Network” that would be going into homes across America. Maybe it was his midwestern roots, maybe it was residue from his days hosting Johnny Carson’s Tonight Show–he did not want someone cursing uncontrollably on his show.

By this point, to show’s staff Madonna appeared to be all over the place, talking about everything from peeing in the shower as a cure for athlete’s foot to insulting Letterman, which was met with boos from the crowd. She asked him if he wore a toupee, to which he shot back “What is that? A swim cap?”. She may have been the biggest star in the world, but this was his playing field, and he was proving why he was the best at what he did. She seemed to want to go for whatever jabs she could, including insisting that money had made him soft and accusing him of kissing everyone’s ass.

MORTON: Thank God for [director] Hal Gurnee. The cutaway shot that Hal Gurnee took of those two old people, the eye that he had and the sense of timing that Hal Gurnee had to break the tension was marvelous. It saved the segment. It really did.

BURNETT: We are all trained to react to Dave, so by and large we all felt nervous as it was unfolding. But I remember thinking to myself, “This isn’t some meaningless actor, this is Madonna going off the rails–I think this might be huge.”

The writers had prepared a top ten list for Madonna to read. When Letterman tried to get her to read it, she crumpled it up and said it wasn’t funny. It was presumed lost to time until this past year when Letterman archivist Don Giller stumbled across it. It read as follows:

My Top Ten Complaints About Dave
10. Couldn’t Vogue if life depended on it.
9. Always asking “Whatever happened to that nice Sean Penn?”
8. Stole his nickname “Material Girl” from me.
7. His top ten lists keep getting lamer and lamer.
6. Can’t fit entire Evian bottle down throat.
5. Driving isn’t the only thing he does too fast, if you know what I mean.
4. Kisses up to Demi Moore way too much.
3. Calls the cops every time I break into his house.
2. Doesn’t look good in cone bra.
And my number one complaint about Dave:
Kisses up to Demi Moore way too much.

After two segments that were laced with profanity and awkward moments, things got even more strange. When it came time for her to leave, Madonna insisted on staying. She was hijacking the show right in front of everyone. She stayed for an uncommon third segment.

KELLISON: That day on the show, we had a grocery bagger competition winner. And we kind of knew that was maybe expendable. But at the same time, Dave loved that grocery bagging competition because he had been a bagger himself as a kid growing up in Indiana. He kind of enjoyed that segment. But we bumped the grocery bagging kid.

At the end, we began to worry that we wouldn’t be able to get Madonna off the stage. And Morty turned to me and said “Danny. Get rid of her.” I started laughing. “How am I supposed to get rid of her?” The implication was kind of like “Well, this is your problem. Get rid of her.” So, I walked out in the commercial break. And Paul was playing a song and I walked onstage, and I said to Madonna “Say hi to the audience.” She waved and as she waved, I took her hand as if I were helping her up. Then I said, “Say goodbye.” She was kind of confused, so she waved, and I led her off the stage. 

With that, Madonna was finally offstage. There was a sense of confusion at the show, mixed with embarrassment. As Madonna returned to her dressing room, Letterman recorded a series of promos, also never seen publicly until now.

Burnett approached Madonna in her dressing room and asked her to do a taped bit for the show titled “What Did Celebrities Have for Breakfast?”. After the way things had gone, he figured this was probably a tall order. To his surprise, she agreed to the bit. (Dead-panned, she answered “scrambled eggs”). If the vibe in the rest of the building was that of embarrassment, the vibe in her dressing room was anything but. To those around her, it felt like a triumph.

BURNETT: She was surrounded by people, all of whom were telling her how great she had been on the show. How the cursing was hilarious. How her playing with a cigar was brilliant. How America was going to LOVE this so much! It was the starkest example of show business sycophantic behavior I had ever seen. I just kept thinking, “They’re all so wrong. And they will all know how wrong they are in about six hours.”

In the immediate aftermath of the incident, the next step was for Morton to call CBS. Of course Madonna’s cursing would be bleeped, but was this something that could potentially embarrass the network? Would they even be able to air it, after having promoted it so heavily?

MORTON: After the show, Letterman was not happy. I was not happy. I called Howard Stringer, who was the head of CBS at the time. And I said “Howard, something happened on our show that I just have to give you the heads up on. I think it’s kind of embarrassing and I think it will embarrass the network.” And he said to me “Fuck the network. Did it embarrass your host? Does your host look embarrassed?” I said “Honestly, I don’t think he looks embarrassed. I think he looks great, and he handles it really well. And Hal got some great cutaway shots.” And I told him what it was. He said “If Dave doesn’t look embarrassed, forget about the network. The network will survive.” 

Which was great advice. And that was the reason we put it on. We always had standby shows ready to go. And we could’ve easily done that. Obviously, it would’ve been a disaster in the press. It would’ve been a mess for us. But we honestly considered it. However, if the show came on and we had a re-run with some actress plugging an old movie, I think it would’ve been disappointing to the audience. 

KELLISON: I felt bad because I knew that Dave was upset a little bit about how it had all gone. He wasn’t happy with how it had gone. But he had done well himself, obviously, given the challenge. Had it gone the way we planned? No. But it was like a prize fight. He went in there and not only did he hold his own, but he certainly gave better than he got, I thought. 

MORTON: Letterman was pissed at me afterwards. I think he was pissed at me for months after that because he honestly thought that I told Madonna to do it. He thought that I told her “Go out and say whatever you want. It doesn’t matter. Use whatever language you want, say whatever the hell you want to say.”

I didn’t do that. I wouldn’t say that. I never would do that. If a guest was somebody who needed a little spark, I might have said that to them. But I would never have said that to somebody like Madonna, that’s for damn sure. 

KELLISON: The swearing thing was very controversial. She said that she had been given permission. Both Morty and I took the heat for that. Morty assumes that I was the one who told her it was okay. I might have told her it was okay to swear, figuring we’d bleep it. But I don’t think I encouraged her in the way that she’d say later.

MORTON: Daniel liked to stir up trouble. He was great at what he did because he always challenged the status quo. He was always looking to stir things up, which was great. It made him spectacular at what he did. But I was always the one who would get the blame afterwards.

BECKERMAN: I think there was a chance that Daniel was terrified watching that segment. Where it’s like “Ugh. Dave’s going to hate this. I’m going bear the blame for letting this happen.” I think sometimes there’s a disconnect between how you think something will be received in the moment and how it obviously in retrospect is. 

KELLISON: Personally, I didn’t care. I think I understood and adhered to the rules that were in place for the show. And I understand why they were there and understood that they reflected his sensibilities and what he wanted for the show. And I respected that. I respected that he wanted to keep the comedy above the belt, and it was more intellectual comedy than primal comedy. I was all for it and supported it. 

It didn’t take long for the incident to work its way into the show’s lore. The next night, Charles Grodin was a guest and gave Letterman his underwear. For his birthday a few weeks later, Madonna faxed him a note that read: “Happy fucking birthday Dave! Glad you could get so much mileage out of the fucking show. Next time you need some fucking publicity, just give me a fucking call. Love, the Anti-Christ.”

Madonna would later claim that everyone was in on it. She told Spin magazine, “The other thing that was ridiculous was that David Letterman knew I was going to do it. I talked to the producers of the show. Everybody was like, this will be really funny if you say fuck a lot, they’ll just keep bleeping you. Well, I came out and started doing it, and David freaked out.”

The feud continued for months, with Letterman taking jabs at Madonna on his show, and Madonna punching in her own way. When Jay Leno did a week of shows in New York, she made a surprise walk-on appearance. Her opening line to Leno: “Can I just say that it’s so nice to have a real gentleman in New York City?”

By the 1994 MTV Video Music Awards late in the summer of 1994, it was time for the pair to bury the hatchet, once and for all.

BURNETT: I remember going with Dave to the MTV awards where he agreed to walk Madonna out. That is when you really could tell how big this had been –just the two of them together got an enormous reaction. Dave said, “I’ll be in the car. Watch your language,” kissed Madonna’s hand and walked off. The place went nuts. So, I guess all’s well that ends well.

Watching their televised encounter again today, it may surprise that such a big deal was made of it. It was front-page news on the New York Post: “STUPID MADONNA TRICKS – Sexy Star Goes Ape on Letterman.” Even The New York Times covered it.

BECKERMAN: I feel like looking back on it, it was a time where if a woman stepped outside a certain boundary of propriety, they’d face a lot more scorn. I’m sure they still face scorn today. But there’s just a lot more acceptance of it now from the culture and from young people and so forth.

KELLISON: We all knew it was going to be this moment in television. I’m sure Dave knew it too. At the time, it was just sort of like “Oh boy. This is a lot.” But very few people could do what he did. I don’t think any other host could’ve done what he did with that situation. Back then it was, from my perspective, amazing to watch.

Madonna went on to appear on the Letterman show six more times. During a 2000 guest appearance, the two former sparring partners reflected on their earlier run-in, which Madonna described as a product of her “rebellious period,” confessing that she’d been angered by his “obvious” jokes. “It’s okay, though,” she joked. “We both were having a weak moment at that time.”