Through the years, a multitude of writers had a hand in the monologue that began Dave’s late-night programs. During the final six weeks of the Late Show, the bulk of the monologue jokes were written by Mike Barrie, Jim Mulholland, Bill Scheft, and Steve Young. It was up to them to come up with five new six-minute sets a week. Barrie and Mulholland had written Johnny Carson’s monologue starting in the early 1970s. When Johnny retired, they started writing for Letterman, but kept their Los Angeles residence.
Bill Scheft: Steve Young and I were the co-head writers of the monologue. He did the clerical work and brought the raw material together. My job, in addition to writing jokes, would be to run through them with Dave.
Steve Young: The weird thing about my job of running the monologue was that I didn’t write many jokes. I mostly organized what Dave picked and asked for more jokes from the various writers. Some days, if things were desperate, I would sit down and write a few jokes where we needed them.
Bill Scheft: Mike Barrie and Jim Mulholland contributed the vast majority of Dave’s jokes at the top of the show. They are prolific, hip, and have changed their tone over the years as the show’s sensibilities changed. They have always been the innovators in self-deprecating jokes about Dave. Hard to pick a favorite joke of theirs, although I loved this line: “People ask, ‘Are you going to miss the laughter and applause?’ Hell, I’m missing them right now.” If anyone else but Letterman does that joke it is disingenuous.
Mike Barrie: I think anyone can do that joke. It may have Dave’s personality, but it has a setup and a punchline. Theoretically Carson could have done that joke.
Bill Scheft: Who else could do that joke? In the hands of anybody else it is a gratuitous plea for sympathy; with Dave it’s a fact.
Mike Barrie: Jim and I wrote from L.A., so my day started very early. I got up at 4:00 a.m. and met with Jim at 6:00. We would meet at one of our houses.
Jim Mulholland: We would fax our work to Dave around 8:30, and he would check the ones he wanted to do and fax them back to us. On a good day we would get a lot of checks, but sometimes it would be two. We really struggled in the beginning. The first day we wrote for him, we faxed eight or nine pages. We had spent several days writing these to make a good impression, and he checked only one of them. It was a joke about Roseanne Barr getting divorced. We thought we were gonna get fired.
Mike Barrie: Then you would hear back from Steve Young, who would say, “Dave only checked one joke on that topic, so we need a few more.” Dave always liked to have several jokes on a topic.
Steve Young: Every day they would send in their pass of jokes to Dave. I would see how many jokes he picked. I usually spoke to Mike and would say, “Dave picked nine; we need more on this or that topic. I saw one good one from this area, if you can try a couple on that.”
Mike Barrie: Steve was the guy who was in charge of the monologue. Steve is a very funny writer.
Jim Mulholland: For many years they were looking for the big closer joke. That could be frustrating. It was a struggle to find the closer. Also, we were sending in the stuff so early that often news would break. Something would happen at 11, and you would have to throw out the stuff you did.
Mike Barrie: We set for ourselves a minimum of four to six pages a day, seven to eight jokes per page. During the course of the day, Letterman would become too familiar with the jokes, and he would start tossing them out. You could be driving on the freeway later in the day and get a call that he needs more on a topic. It was a lot of hours and vastly overwritten to get fifteen jokes that Dave liked.
Steve Young: Jim and Mike are very professional and prolific. Being thousands of miles away and being a voice on the phone is very different from being in the writers’ room. They had been doing this for many years.
Jim Mulholland: Someone once said to me, “You know, there are these two mysterious guys. They write all of the jokes, and no one has ever seen them.” He didn’t know I was the guy. No one ever saw us because we were never in the office. I didn’t want anyone to see us getting older and older. We were like these shadowy characters. “Who are these guys sending these jokes everyday?”
Bill Scheft: Dave would start the monologue with a “Hi, how are you?” joke about himself or New York City, and then we would try to pair up jokes on topics.
Jim Mulholland: Bill suggested we write New York City jokes, which we started doing. We were good at that because we did them for Johnny when he was in New York. That was how we got our footing on the show, with the cab drivers, subway, or rat jokes—all exaggerated nightmare versions of New York City which no longer existed. It was more like the New York of the seventies. Dave loved that stuff, and that got us going.
Steve Young: There was a certain rhythm to it that he grew to feel was right for him. “Here is something about the weather” or “I was walking on Broadway on my lunch hour”—something not deeply topical, to dip our toe in the water with something harmless.
Bill Scheft: From 1995 on is when the monologue became more topical. He realized if you do topical stuff you don’t have to take forever to set something up. If it’s in the ether all you have to do is say, “Here is news from the O.J. trial,” and they know where you are. You can go right to the punchline.
Jim Mulholland: It didn’t look like we were the right fit for him, but as it went on I think we had an influence on him to do more topical stuff.
Bill Scheft: I remember a great joke in the middle of the Bill Clinton scandal. I wish I had written this: “Clinton claims that oral sex is not sex; if that is true there is a hooker who owes me $75.” That is a kind of joke that none of the other hosts did. Dave would take a global topic and the joke would be about him. That is when he was at his best.
Steve Young: Dave didn’t want anything to go beyond one cue card. It was minimal—a few words, a phrase and a setup. He would then, depending on his mood, improvise off that. He might have thirty seconds of off-the-cuff conversation leading into a joke that was not on the cue card.
Jill Goodwin (Non-monologue Writer): When I started working as Barbara Gaines and Jude Brennan’s assistant, I would see that the mailroom guy would get monologue jokes on the show. I started asking around, “So anyone can submit jokes?” They said, “Yeah, go up to the fourteenth floor and give some jokes to Bill or Steve.” One of my jobs at that time was processing the payments to freelance monologue writers. If a joke aired, they would get $75 or something. That was attractive to me. I can try to write jokes, and if they air I can have a little money for the bar. Everyone was supportive. Once they saw your name on the monologue joke sheet that went around, Barbara would say, “Hey, you are writing jokes. Do more.”
Barbara Gaines: We were so proud. We didn’t want to lose her as an assistant because she was fantastic, but we wanted her to succeed. We loved Jilly because she was so funny. She would make fun of us, and we liked that.
Jill Goodwin: They were very supportive. Bill Scheft was so nice. He would say, “This is funny, but it needs to be twenty words shorter. The punchline needs to be here.” He would mentor me.
Bill Scheft: When I got the job with Dave, I asked if there was advice he could give me. He said, “Don’t write a joke more than four lines. I don’t care how good it is, if it is longer than four lines it won’t fit on a cue card.” The jokes on Late Night were all three and four lines. At the Late Show, most of the jokes were two lines.
Mike Barrie: You’d write “retirement,” and he would say whatever he wanted. The second sentence was written out on the cue cards. That doesn’t mean it was always told that way.
Bill Scheft: The show was on NBC for eleven years. The sensibilities in the eleven years, maybe, changed twice. In twenty-two years at CBS I think the sensibilities of the show, in terms of the content, changed half a dozen times, because he got older. He deserved to be the kind of host he wanted to be. When we first came to CBS he doubled the monologue, doing eight jokes, but on eight different topics.
Jim Mulholland: It was hard to do a lot of material. As the years went by we got him to do more. When we started with him on the CBS show, it was just a handful of jokes, so you couldn’t really get into it.
Bill Scheft: The thing that changed that was the O.J. verdict. When the verdict came down, he said to me, “I think we should do the whole monologue on O.J.” We did that. It really worked, because if you are doing eight jokes on eight topics, it’s just going from joke to joke. That is when the monologue became more like stand-up. Don’t confuse being a stand-up with doing a monologue. With stand-up you work ten years on a routine. A monologue, you have one shot on one night.
Jim Mulholland: He was doing a longer monologue. Maybe it went from six to ten jokes.
Bill Scheft: At NBC he would do three jokes. Then, after Johnny left, he went from three to four jokes. When he went to CBS, he went from four to eight. So for the first ten years at CBS it was eight jokes, no videotapes. Then it changed to eight jokes and two taped pieces at the end of the jokes. Then the monologue, which had been considered, unfairly, his weakest quality, started testing very high. So he decided to double it.
Barbara Gaines: The monologue was just Dave. That was his piece. Bill worked almost entirely on the monologue, so it was extremely important to him. It often got criticized, so he would defend the monologue. Bill’s place there was much more than just the monologue. He was Dave’s friend. That was his place in history, as Dave’s comedy friend.
Bill Scheft: I stood under the stairs. My title was writer, but my job was entertaining the man during his own show. I would keep him loose. I was a corner man. We didn’t talk about the show. We talked about nonsense. I would remind him of an old comic’s bit or something on a previous show.
Barbara Gaines: Bill would interject during a desk piece or have an answer. Bill is a Harvard boy. He is a good person to lean to the left and talk to. He could lean to the left and talk to me and I got nothing.
Mike Barrie: Bill is hilarious and a brilliant writer. He has written novels and is very funny on his feet. He is the last person to see Dave before he goes on, so he can give jokes to Dave in the last five minutes. I think they had a rapport that worked for both of them. Bill’s humor is smart and hip, and so was Letterman’s. I think they fed off each other. It was a good marriage.
Bill Scheft: Let’s say of the twenty-four jokes on cards that Dave had personally selected, he looked at a hundred jokes. Steve and I looked at 200 to 300 jokes on an average day. The monologue had sixteen elements: thirteen jokes and three short tape pieces, a live interrupt or a prop.
Jim Mulholland: He wanted to do nineteen, twenty jokes, which he did for a while, which was very exciting, but then it sort of evolved to the cutaways and videos, so it wasn’t as much.
Steve Young: I couldn’t micromanage too much because most days during the show I was going down to the edit room to edit a fake commercial. The monologue was probably twenty-five percent of my time and energy.
Joe Grossman: You have monologue writers, and other shows would call them “sketch writers,” but at Letterman you were not allowed to use the word “sketch.” There were four monologue writers, and the rest of us would be writing everything else, which included those videotaped pieces or interrupts in the monologue, which we called “extras.”
Steve Young: That was an evolution. I think we became aware that other shows started doing that. It did seem like the natural thing to do. Part of the reason we hadn’t done it in the show’s history was the technology had improved so much. It was more practical for us to produce seven or eight videotape pieces per day and let Dave choose three he liked. When I started on the show in 1990, if you wanted to put together a videotape piece it would be so technically challenging. We would produce one thing a week, but by 2015 we could produce seven or eight a day.
Joe Grossman: In terms of videotaped pieces, I would say they started showing up during the monologue roughly around 2006-2008. Before that they would be in Act 2 . They were called “extras,” because they were little extras to throw in the Act 2 desk piece. Then we started moving them into the first act.
Bill Scheft: The last three or four years we realized because we’re doing so many more jokes, that we thought it would be better to weave the tapes and interrupts within the monologue. That is the way we did it. Ideally we closed with the strongest tape.
Steve Young: I don’t remember when there was a greater turn in the monologue to the retirement jokes.
Jim Mulholland: We had a year to do retirement jokes with him. I loved that. You look for anything when you are a monologue writer. We did jokes about him sitting in his robe watching Ellen, stuff like that. “Tonight I am interviewing Oprah and next week I’ll be hanging out at Ace Hardware.” We had jokes like, “I am leaving the show, but I’ll be back at CBS in the fall and I’ll be solving murders.”
All the jokes highlighted in this chapter were written by Mike Barrie and Jim Mulholland. They graciously shared pages of their jokes for the book. Just for old-times’ sake, I checked off only a portion of them and sent the rest back.