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Bill Scheft is a novelist, columnist, and television writer for the Late Show With David Letterman.  His most recent book is Everything Hurts.

A conversation with the novelist and David Letterman Show writer.

Question: How did you get started in comedy?

Bill Scheft: I was always funny and my family is funny. I’m the fifth of 6 children; from a large Jewish family—there was never enough guilt to go around. When I was 18, I was at Deerfield Academy and me and a few of my friends might have stolen a faculty member’s car and drove into North Hampton, where I did 7 minutes of stand up—mostly stolen material—in a bar called the Early Times.

From the ages of 18 to 22, I think I probably performed twice a year. I won my undergraduate talent show at Harvard doing stand up and it was always something I knew I could do. It was always a hobby with me, but I had the feeling that if they’re not Cameron Crunch I could make a little money at it.

I majored in Latin at Harvard because I thought the church was going to come back. It’s one of those things, where I majored in the Latin and Greek because that was the only thing I really was interested in academically. I think it’s the best preparation for a writer because it teaches you the value of a word and of the word and so, I went to Harvard fully intending to be either a Latin teacher or a pharmacist. I mean, really, what can you do with a Classics degree?

I think got a C- in a graduate course, my freshman year, in Herodotus and then I turned my sights to becoming a sportswriter. I did that for a while and them I became a stand-up comic for 13 years, and in 1991 I was hired by Late Night with David Letterman at NBC and here we are.

Question: Who are your comedic influences?

Bill Scheft: When you’re 16,17, and 18 and you’re staying up and you’re watching the Tonight Show—this is the early and mid 70s, it’s George Carl and Richard Pryor, I was introduced to Lenny Bruce when I was 18, he’s a huge influence not on my stand up but on me wanting to become a stand up—I was just one of those guys that I would watch the stand ups, “Boy, that must be great to do yhat.”

You never think that that’s what you’re going to do, but I ended up doing it for 13 years. I don’t know who’s this line is, but it’s a great line one, “People become stand-up comics the same way a woman becomes a hooker—you start doing it for a couple of friends and then you realize you’re good enough to get paid.”

Question: What was your niche as a comedian?

Bill Scheft: When I was a comedian, my act was Jews, sports and weather. I talked about being Jewish, I did a lot of sports material because I was a sportswriter, and I later on I had my own humor column in Sports Illustrated for 3 years called The Show, which I love. It was the perfect marriage of all my careers—just topical jokes about sports every week.

I’m going to steal Dave Letterman’s line about his stand up career. “I was good. I was a good stand up but I was never going to be the guy that you pay 20 dollars to see.” Unlike my wife who still performs, my heart wasn’t in it. I didn’t have to be up there. I was good enough to be up there. I made a living at it, but boy, 12 years in and you wake up in a Motel 6 in Covington, Kentucky and say to yourself, “I’m not in show business. I’m just Willy Lowman with a bag of jokes.” I’m just going from town to town trying to get the people in a different town and that’s all it was. But I was one of those guys that was out there; I did every television show except the ones that could help your career.

That was part of my master plan—it was so funny because they knew me at the Letterman Show not as a writer , but because I used to audition to try to get in the show as a comic. I had a line in my act which has been, I’m proud to say, has been stolen by several comics. I said, ”For those of you here in New York, it’s great. The Dyslexic Theater Company is in town and they’re doing Annie Get your Nag.” Bob Morton, the producer of Letterman, said, “If you have 6 more minutes and as good as that one line, I will put you on next week.” Sadly, I didn’t.

I had some good lines. I’ve forgotten them all. A couple of years ago I wrote for Chris Rock on the Academy Awards and he hired a lot of comics to write; it was a lot of people I hadn’t seen for a long time because I stopped performing. Carol Leifer was one of the writers and we went out the first night out for Chinese food and Carol Leifer said, ”Every time I have Chinese food I think about your bit about Chinese food.” And I said to her, “I’d love to hear it because I have no recollection of this.”

The bit was, “When you go out for Chinese food they take down your order in Chinese. How are you supposed to dispute this bill at the end of the meal? Excuse me waiter, I didn’t order the television antennae.” That’s the kind of cutting edge stuff that came out of me.

Question: How difficult is it to consistently write funny material for “The Late Show With David Letterman”?

Bill Scheft: First of all, thank you. I’m glad that the question is phrased so that it’s assumed that I write funny stuff everyday. I appreciate that. I think if you write for a strip show, which is what Letterman is, a show that’s on 5 days a week, you don’t think about it in terms of funny. If I ever thought about what I had to do at the beginning of everyday, I don’t think I could do it.

With comedy writing, especially writing on a daily basis, it’s a muscle that you work and, if you keep working it, you can do it. What Woody Allen once said about joke writing is, “If you can do it, there’s nothing to it,” and I believe that.

Mostly, with the Letterman Show, I’ve been a monologue writer. I just write jokes for the most part, though I work on some other stuff on the show. When I first started the show in 1991 and they told me I have to write 15 jokes a day I thought, “How am I going to do this?”

I just tried to get through that day, and then within about 6 months I wasn’t writing 15 jokes a day—I was writing 25 or 30. It got to the point where I was writing 50 or 60 jokes a day, and they’re not all great. Actually, very few of them are great ,but that’s the thing about comedy—you have to make mounds and mounds of coleslaw to get one good serving. That’s what we do on The Letterman Show. We just create a lot of content and ideally the best content gets on the show.

Question: How much does Dave Letterman himself contribute to Late Show material?

Bill Scheft: Here’s the thing about the writers and Dave Letterman. We write a lot of stuff that’s funny. We write a lot of stuff that’s pretty good. We write a lot of stuff that’s lame. But invariably, night after night, the funniest moments in the show are Dave reacting in real time to his surroundings. It’s something that you can not write in preparation for the show, but all he wants when he goes out there is to feel like he has enough of a life raft.

I want to say that again: when Dave comes out at the beginning of the night, the writer’s job is to put him in a situation where, if he needs it, it’s there—the monologue is there if he needs it, the top 10 is there if he needs it, couple of good tape pieces are there if he needs it, and then he can just relax and react in the moment.

I have a friend, Kelly Rogers, who I started with, who was a great comic that people don’t know about. She said something so profound: “Your act is for the nights when you’re not funny.” That’s what the writers supply to Dave. They supply him an act for those nights when he doesn’t feel funny—and I have yet to see a night like that.

Question: Where does Larry David get ideas for Curb Your Enthusiasm?

Bill Scheft: Larry and I used to talk about this all the time at the beginning of the show, because originally they got picked up for four episodes. He would say, “I have just enough for the 4 shows that we’re doing, but after they pick the show up, I don’t know what to do and I have no ideas. What am I supposed to do?” I said, “Larry, it’s eight in the morning. I just woke up. Please.”

It’s one of those things—the longer you do it, the more things occur to you. Of course, now Larry David, having worried about that at the beginning, figured out a way throughout the years to incorporate his life into his work. You know how you’re out at dinner with friends and somebody says something or something happens and somebody at the dinner table says, “This is just like an episode of Seinfeld”?

Okay, that may or may not happen, but when you’re with Larry David you never know when a scene from Curb Your Enthusiasm is going to burst out. I’ll give you an example: a couple of years ago Larry and I were having dinner and we got to the end of the meal and I said to him, “How about some dessert?” He said to me, “No. No dessert for me. Ted Danson and I have a bet. No dessert for a year.” And I thought, “Wow. It’s Larry David. It’s Ted Danson. They’re both billionaires. The bet is no dessert for a year. I mean, the bet has got to be at least $50,000—make that $100,000, maybe a million dollars.” I said to him, “How much is the bet for?” He says, “Two hundred dollars.” I said, “Have a piece of frigging cake.”

Question: How similar is Larry to his on-screen persona?

Bill Scheft: Let me just say this about Larry David: try as he might to distance himself from the character that the world sees, he will be unsuccessful. I know this guy.

There’s a great expression, “Alcoholics are just like everybody else except more so.” And Larry David is just like the guy you see in Curb Your Enthusiasm except more so.

Question: How has fame changed Larry?

Bill Scheft: Well, let me just say this about Larry. I wish this was my line, but somebody once said about famous people--when they get famous, they don’t get better. Larry David is the exception to that, because Larry, as he has gotten better known, is much more comfortable in his skin than he used to be, and much more self aware.

I’ll give you an example. We’re at a Yankee game last year and a kid—18, 19 years old—comes up with a pen and paper and he says, “Mr. David, can I get your autograph?” Larry says to him, “Come back after the inning because this time is no good. I am in the middle of the game.” And the kid says, “Well, I can’t I’ll lose...”

“Come back in the…you know after the innings. I am watching the game.”

The kid says, “But you don’t understand, unless…”

“No you don’t understand!” Then, hearing himself do that, he burst out laughing and signed the kid’s paper.

I have to tell you: 15 years ago, that does not happen. 15 years ago, this whole scenario winds up in small claims court.

Question: How has the Late Show kept up with a culture in which former taboos are now commonplace?

Bill Scheft: So, I’ve been at the Letterman Show since 1991, that’s 18 years. I would say, during that time, the comedic sensibility of the show has changed half a dozen times because Dave has gotten older, but the average age of the average writer had stayed the same, so they bring in their sensibilities on what they think is funny, and they try and interject it in the show.

So the show’s comedic sensibility changes, and it’s all valid. We don’t write anything and think, “Oh I need to write this joke to appeal to the crucial male, 18 to 34 demographic.” We don’t think like that, at least I don’t. I just think, “What’s the funniest take that I can do?”

Sometimes I think that things have passed me because I’m older and the people watching are younger, but funny is funny is funny. If you show somebody a Marx Brothers Movie who’s never seen one, I think that they’ll think it’s funny. I don’t think they’re going to ask, “Why isn’t Groucho naked? I want to see Groucho’s deal!”

Question: How has late night comedy in general changed?

Bill Scheft: Late Night has really changed in the last three decades. First of all, there’s more variety and more competition. Before 1982, there was Johnny Carson and people that he knocked off. All of Late Night was Carson, and it was a monologue, some sort of bawdy, broad comedy aimed at people over 30—white men over 30.

Then, Dave came along in 1982 and NBC gave Dave Letterman one directive: whatever you do, we want it not to be the Tonight Show. We want a 3 joke monologue, not a 25 joke monologue.

Given that go ahead, it was very free flowing, it was irony-based, and it was, as the old producer Bob Morton used to say, “Late Night with Dave Letterman celebrated failure.” It was not sleek, it was very anarchistic.

Then, you have Dave moving to CBS at 11:30 and you have this situation with Jay, where you had one show that was host driven and concept driven—which is Dave—and another show—which is Jay—who was just essentially just a comic who got his own show: a monologue and guest, a little more traditional.

And then you had the 12:30 shows with Conan. David started this with going after the younger audiences—people always say, “I started watching Dave in college.” So there was a real market out there, and like I mentioned before, Late Night became this very lucrative industry for the networks, very cheap to produce.

Of course, once people start making money, it’s going to tend to get watered down and it’s not going to be as fearless because there are a lot of people whose livelihoods depend on your success. It’s not just kids crawling around anymore.

Then, what happened in the late 90s is that cable emerged as a late night force, with the Daily Show Steve Colbert, and it was much more topical. Not that the Letterman Show didn’t always take care of what was in the news, and so did Jay—but it became more topical and more issue-oriented, and I think we’ve certainly gone in that direction at The Late Show. So that’s the evolution of that.

Now, I think that if I was to predict—and believe me I’m always wrong so put your money elsewhere—I think we’re going to reach a critical mass with the topicality thing because I think it’s going to get a little too partisan and late night shows are going to be put in a situation that they shouldn’t be put in, unbeknownst to them. I think it’s probably going to go back to being a little sillier and less celebrity driven and easier to take unless “foe” serious. You look at the guy like Craig Ferguson and watch what he is doing. Nobody is doing what he is doing, and I think he will emerge. He is silly, it’s all him. The guests don’t really have to say anything. He is going to take care of it. I think that’s where we’re going.

Question: What do you make of comedy’s newfound political influence?

Bill Scheft:  I don’t think that Johnny ever dreamed that he would influence an election. He never talked about Watergate when Watergate was going on. He talked about it after the fact, but now Tina Fey had as much to do with the last election as Dave did, with the situation with McCain, as the Daily Show also does.

That’s where we are with these shows—and none of these shows set out to influence elections, but that’s what happens. They’re right in the popular culture.

I never bought all those studies and surveys about people getting their news from late night television, and I still don’t, but I don’t think that people turn to late night television to see what the point of view is on the news. I think they know going in. I don’t think we’re in the education business.

Here’s the deal with society, how about that? For Big Think, here’s the deal with society. People fall in love with the idea of things rather than the reality of things, and that holds true for late night. It’s so much more provocative and sexy to say that people are watching our show and getting their news from Dave Letterman, and let me tell you—as somebody who writes monologue jokes and somebody who knows Dave—I’m telling you we find that very funny.

Question: What are the differences between writing for the Late Show and writing comedic fiction?

Bill Scheft: Well, here’s the difference between writing monologue jokes and writing fiction. Well, first of all you use the word intern much less and waterboarding much less when you write fiction. It’s a different muscle. Writing monologue jokes or writing jokes for a nightly show is a volume business—you’re just turning out quantity and then panning for gold. In the words of the Steroid Universe, you‘re using your quick twitch muscles. You’re just firing quicker and you’re reacting quicker and it’s all about “How many different takes to a premise?” That’s writing comedy for television.

Now, writing humorous fiction, everything slows down. It’s a different muscle and it’s a state of mind. I think writing jokes is a real physical practice, all free association, and writing fiction, it’s getting into a state of mind where you’re inhabiting this world of these characters you created.

For me, writing fiction: I want to be funny, I want my premises to be funny, I want my situations to be funny, I want my characters to be complicated— but, however chaotic, it must be plausible. The thing about a lot of great monologue jokes is that they are not plausible. They are sort of a little, “Really?”

If you ask me, “How did you learn to write fiction?” Well I learned to write fiction writing for Dave. We’ve had some jokes about Hilary Clinton and Dave would say, “Let’s just start it with, ‘Hey, have you heard? Hilary Clinton’s going to jail.’” Well she is not, she never was, but he loved that. It was a grabber. You could get a laugh and then he could come down off it and laugh off the joke.

That might find its way in somebody else’s novel, but it’s never going to find its way in mine. I’ll give you an example: when Hillary was elected to the Senate and then Bill was out of office, there was a story in the “Times” that he was a little lonely in Chappaqua. He was sort of rattling around the house so he would go down once a week and have breakfast in a coffee shop in Chappaqua and that’s kind of quaint, it’s kind of charming.

Well, that wasn’t good enough for us. It wasn’t good comically, so we did jokes for two weeks about him hanging out in singles bar in Chappaqua. We just made up all these, it was great, and we had a ball with it and is it. I guess I’m sort of arguing against myself because it is a little plausible that Clinton might go to a singles bar, but we just made it up and people knew we had made it up and it was very valid as comedy.

The best advice I ever got about writing fiction was “make your characters’ lives complicated because, we all have a story unless it’s our autobiography.” I know we think our lives are fascinating. God knows I do, and it may be very well fascinating, but it ain’t complicated.

Question: What challenges and opportunities are presented by writing fiction about your own life?

Bill Scheft: This is my third novel, Everything Hurts, and it is born of real life. This is a book about a guy trying to get rid of a psychosomatic limp and he seeks the aid of a legitimate self-help guru. He’s an accidental self-help guru, and to cure him of his psychosomatic limp he seeks the aid of a legitimate self-help guru. This is born of real life because for three and a half years I dragged a foot. I limped. I was in constant pain, and it confounded doctors. X-rays and MRIs turned up nothing. The pain moved around. There was no consistent symptomatology. It came and went of its own accord. It made no sense to anybody, but I was in constant pain and so I sought the help of guy who specialized in psychosomatic pain. He believes that the pain is caused by unconscious rage driving to your conscious mind and your conscious mind is so threatened by the coming rage that it tries to distract you by giving you pain to a vulnerable area. That’s his theory. I still believe in it.

His approach is to examine your past. So, I’ve been seeing him for a little while and I said, “You know, what I’m going to do? I’m going to write a novel about a guy trying to get rid of a psychosomatic limp and try to out myself out of this pain.” and I started writing it. It took me 2 years to finish. Two years later I’m finished with the book, son of a bitch, and the guy in the book is fine. I’m still dragging a foot and in constant pain. So, I sold the book to Simon and Schuster.

Ten days after I sold the book, I went to yet another doctor, took another look at another x-ray and said to me, “You need a hip replacement. I’m not telling you you should get one. I’m telling you you have to get one.” This is a no brainer, and so last July I got my hip replaced, I’m out of pain, I feel great, and everybody who suffered along with me said, “You must be furious. Three and a half years limping in constant pain.” and I say the same thing to all of them: ”If I haven’t done that I wouldn’t have gotten the book out of it.” So, you know, the journey is the destination, right?

Question: Is writing about a traumatic period in your life a cathartic experience?

Bill Scheft: Was it cathartic to write this book? You have no idea, because as I mentioned, I was in constant pain and one of the few times that I was not in pain was when I was writing—I mean writing at the Letterman Show or working on the fiction, but at the end of the, I’d come home and relax, put my feet up, with incredible pain that could not be relieved by any pill or anything like that.

This book is a reflection of that and I’m sure people have said this before but, “Artists create because they have to, not because they need to, and not because they think they should—because they have to.”

This was a classic case of it, so it was very fulfilling. It was very ambitious because I was suffering while I was writing it, and the guy is getting better, and I was aspiring to the character I was writing about. Boy I’d love to recreate that in my next book. Wouldn’t that be great?