Long-Time Letterman Writer Bill Scheft on ‘Late Show’, Writing Novels vs. Writing Jokes, and Stephen Colbert
Tonight, when David Letterman saunters on to the Ed Sullivan Theater stage to deliver his monologue, flanking him will be two men whose tenures date back to the groundbreaking Late Night With David Letterman: To his right, bandleader Paul Shaffer; and to his left, writer Bill Scheft, who Late Show viewers have undoubtedly come to know as the bespectacled man off in the corner, surveying the proceedings. If hosting a late-night talk show is an hour-long prizefight, Bill Scheft is Letterman’s corner man.
Since joining Late Night in 1991, Scheft has garnered 16 Emmy nods; while also serving as writer for two Oscars, head writer for 3 ESPYs, and special contributor to the Emmys, Tonys, and Grammys.
Additionally, his prose has appeared in the New Yorker, The New York Times, Esquire, Slate, the short-lived but highly influential Modern Humorist, and the New York Times Book Review, to which he contributes regularly.
His latest and fourth novel, Shrink Thyself, was released June 10th.
Below, he discusses, among other things: simultaneously writing a novel and late night television, Letterman’s controversial Oscars hosting performance, performing a revue of Larry David’s cut SNL sketches, the real inspiration for Elaine Benes, and Stephen Colbert.
Shrink Thyself is your fourth novel in 12 years, and in the meantime, you’ve continued writing for The Late Show. What was your process working on this novel, and how do you balance it with working on the show?
The process has always been pretty much the same. Pot of coffee and six Vicodin and then we’re off… I work on my fiction Wednesday mornings for a couple of hours before I go into the show and then on weekends and during hiatus weeks. It takes around two years to complete a first draft.
Writing fiction is completely different from writing jokes for a strip show. Two different muscles. Joke writing is a volume business. You use your “quick-twitch” muscles. It is all about generating material for that day. Even the interrupts and taped extras we do. They’re concepts, but they’re just for that day. When I write fiction, or try to write fiction, everything slows down. It is about getting in a state of mind where you can inhabit the world and the people you’ve created.
Is there ever any overlap with material?
Not much. In The Ringer, the character of Dan Drake is what I imagine Dave would be like if he had a radio show. And if I’m stuck to come up with a name, I may cop one off the staff. (Production associate Thea Kalcevic makes an appearance at the end of Shrink Thyself).
Do you have a preference for either?
That’s a little “Who’s you favorite child?” I love both because they are so different. Each one is a welcomed escape from the other. Writing topical jokes or slapping a button on some short piece is propelled by the energy of constant free association. And if you do it long enough, you know when you’ve come up with something no one else has. Dave did a joke of mine a couple of weeks ago about the Taliban prisoner exchange: “It was a 5-for-1 deal. President Obama got the idea from a commercial for a sportcoat sale at Joseph A. Bank.” That was very satisfying. If you’re locked in, you can come up with a couple of those a day. My experience with fiction is that you have to stare it down a bit. You’re always asking yourself, “Is this plausible? Is this what I’m trying to do? Does this actually sound like a real person, or am I showing off?”
Mark Twain’s wife was the first person to read whatever he happened to be working on. Considering your wife is comedian Adrianne Tolsch, is it safe to assume she’s involved in the editing process?
When people ask me, “Is your wife funny?” I always says the same thing, “No, she’s funnier.” That said, there are three people who read everything I write as I write it. Two of them are women. My wife and Late Show Executive Producer Barbara Gaines are the first stop. They know that the only valid note, the only thing I must must know, is whether or not something is unclear. Something doesn’t follow. Believe me, I’ve had these conversations: Adrianne: “When is Dino coming back? I love him.” Me: “Uh, Dino died.” Adrianne: “He died? When?????” That? That’s the kind of shit I need to hear, and address. Everything else is just conversation. The one guy is a retired English professor named Don Harrell. And the only thing I ever get from him is “Hey, keep going.” And really, what else do you want to hear?
Have you always had literary aspirations?
If you had asked me at 10 “What do you want to be when you grow up?” I would have said, through my buck teeth, “An author.” And since we don’t have a time machine, you’ll have to take my word for it. And now that I’ve said that, even though it’s true, turns out at 10 I wasn’t being prescient, just grandiose. Once I started writing sports, then jokes, then scripts, it became clear to me that the 10-year-old me was full of shit. Clearly, I did not have the gene in me to write the long form. I was only good in installments.
When I was a sophomore at Harvard, I read a novel called The Doctor Who Made House Calls by Milton Bass. A minor minor minor work. I read it and thought, “I would give anything to write something like that, but I know I never will.”
So, I kept my dreams to myself until I met Monica Yates, Richard Yates’ daughter, who was going out with my friend Larry David. (Don’t believe what you hear on the street. Monica Yates was the basis for Elaine Benes in Seinfeld. End of story.) I was performing in a revue of Larry’s sketches that had been cut from his year working on Saturday Night Live. This is 1987, before he became the Industry Known as Larry David. Larry shows up at a rehearsal with a copy of The Easter Parade. I say, “Where’d you get this? This guy is my idol.” Larry says, “I’m going out with his daughter!” Back then, the fact that Larry was going out with anybody was news, but Richard Yates’ daughter? So, she comes to the show, and I can’t wait for it to end. I run up to her and say, “Please give me your father’s address. I want to tell him he’s the greatest author of the last 50 years.” She does, then I tell her, “I would give anything to be able to write a novel, but I don’t have the gene in me.” You know, the thing I just said to you. She says, “How old are you?” I say, “30.” And Monica Yates says, “You’re a baby. Nothing has happened to you yet. Wait.” Eight and a half years later, I started my first novel, Who Listens? The one never got published, but it didn’t need to. It proved to me I could do this.
Shrink Thyself centers around the protagonist’s decision to no longer undergo therapy. Is this something that came from personal experience?
No. It came from my wife. She was seeing a therapist for a few years. A guy who, coincidentally, I had seen previously for a while. She took care of what she needed to take care of, and after she stopped sessions, they would meet for dinner like twice a year. Like friends. They still do. And he would share things with her about his life, not heavy things, but stuff like “We had a flood at the house on Fire Island… My program is waiting for government funding….” and I would be amazed, because I knew zero about the guy. Which is the way it’s supposed to be with a therapist. So, that’s where I got the piece about a guy ending therapy and trying to become friends with his therapist.
The idea of the non-psychological life came from the stone fact that in every one of my previous novels there had been at least one unorthodox shrink. I told myself, “Bill, you cannot do this anymore. This next novel must be non-psychological. No more self-obsession. No more crazy shrinks. So, I’m about five pages in, and Charlie and his shrink are ending therapy and they’re going to be friends and I think, ‘Okay, just one more time…but this guy isn’t going to be merely unorthodox, he’s going to be really fucking nuts. He’s going to be beyond inappropriate.’ That’s when the book changed from a guy just trying to live the unexamined life to a guy who the second he makes that decision, things begin to happen that would send anyone else screaming back into therapy.
Two of your books have been optioned for film. What’s that process like?
If you look at the whole thing as a chance for a two-hour commercial for your book, the process is glacial but benign. And if you can do that, you’re probably a Buddhist. But when you see the contract and run the numbers and think, “This will solve ALL my problems and finally, everyone can kiss my ass….” that’s when it gets tricky. My stories are no worse than anyone else’s, except it happened to me. The Ringer was optioned by United Artists just after the book came out in late 2002. I got to do the script, which was a wonderful exercise, and on the basis of my script, a year later, the movie got greenlit. We found a director and were going to begin casting in early 2004. Then, two things happened. The President of United Artists, Bingham Ray, who was a real champion of the film, got fired. And then MGM/UA got bought by Sony and all the “go” projects were poison. Except Capote. That loser sneaked through. Since then, I have a conversation every five years with someone who wants to do it. It took my friend Elinor Lipman 19 years and a dozen options to get her first novel Then She Found Me made. What’s this, 2014? So, I got seven years left.
Everything Hurts was optioned two years ago, and this had all the signs of happening, and happening fast. The team that did Our Idiot Brother (Jesse and Evgenia Peretz, David Schisgall) bought it, which means you get the director and the screenwriters, and they have a tremendous reputation for working outside the studio and raising their own money, then scoring on the sale at festivals. We had a lunch and I was very fond of all of them, which, like I have to tell you, does not usually happen with me and people in the picture business. But they could never break down the book to their liking and it went away.
How did your position at Late Night come about?
I was a standup from 1980-1993. When Late Night came on, I tried first to get on as a comic, but I was not the kind of act they were looking for. But I got to know all the producers who came into Catch a Rising Star, where I was an emcee. Robert Morton, Paula Niedert (who married Chris Elliott), Cathy Vasipoli (who married Paul Shaffer). But all I ever wanted to be was a writer. Standup was how I made a living. So, I started making submissions. I submitted to the show in 1984, 1985, 1987, 1988 and 1989. Never ever ever came close. The first week of October, 1991, Adrianne and I are having brunch at the Friars. Morton comes in. I go over to him and say, “Are you looking for anybody over there?” and he says, “Nah. But you know what you should do? Just write some jokes. Dave is always looking for jokes.” All my previous submissions had been developed comedy ideas for the show. Maybe three half-assed, side-of-the-mouth monologue jokes up front to fill it out, because that was all Dave did at NBC. Three jokes. Sometimes two. So, I wrote ten jokes a day for a week and, remember this is 1991, hand-delivered them to NBC a couple of hours before the taping. Thursday night, I get back to my apartment, message on my machine from Morton. He leaves this message, “Hey, Dave did one of your jokes tonight. Nice going.” I know you’re dying to hear the joke. I’m still proud of it:
Elizabeth Taylor and her new husband, Larry Fortensky, had their first fight. It was over whether or not he should unpack.
He did another joke of mine the next night (“We’re learning more and more about Supreme Court nominee Clarence Thomas. Turns out his nickname in college was ‘Dice.'”) Morton again calls me and now he says they have an opening for a monologue writer. The next week was a dark week for the show and I was out working in Las Vegas. I took the red eye in Sunday and met with Dave Monday afternoon. We spent 20 minutes talking about cigars (I smoked a lot then. A lot.) and other comics. He kept saying, “I hope we can work something out,” and I’m thinking “Just fucking ask me!” Steve O’Donnell, the head writer, called me the next day, October 21. I started the following Monday, October 27, 1991.
The show itself was extremely experimental and non-traditional, did you find it challenging to maintain that sensibility while working with something as static and traditional as the monologue?
It has always been challenging because every day the process begins anew. I never viewed it as static, and I find the traditional element comforting. But within that, you’re always trying to come up with the take no one else thought of, or something that tickles you. And I think the show still is experimental. The writers are always tinkering with the form.
One of the things I’ve enjoyed most about both Late Night and then The Late Show is the utilizing of people like Rupert Jee, Biff Henderson, the stagehands, cue card operator, etc. You see his today in shows like Tim and Eric. Was there a conscientious decision to include them, or was it something that took on a life of its own over time?
Rule number one at NBC: Don’t be Johnny’s Tonight Show. So, no “Mighty Carson Art Players.” Using non-actors was always more interesting, because it chased away the slickness you get when using actors. And, as someone once put it, it celebrated failure.
You were heavily involved with Dave’s notorious Oscar hosting gig in 1995.
The fact that people still link Dave’s performance at the Academy Awards with Jay supplanting him is beyond ludicrous. Jay never won a week until June, 1995. The Oscars were held at the end of February. So, what happened? Viewers waited four months, then remembered Dave had done poorly and decided to punish him?
18 years later, I only have two regrets about the night, both of which happened weeks before the show, neither of which I could have altered: 1) The decision to have Dave appear only 17 times during the telecast instead of 24; 2) The decision to run the cab driver remote first and the Cabin Boy auditions (with all the big stars), second.
What was your experience like writing again 10 years later?
Chris Rock, who I had known since he was 18 when he showed up to Catch a Rising Star with the untucked white shirt three sizes too big and the jeri curl and made you pay attention immediately to how good he was going to be, hired me as well as a lot of other comics and writers he had worked with, was influenced by or just liked having in the room. Jeff Stilson, the late Richard Jeni, Nick DiPaolo, Carol Leifer, Frank Sebastiano, Lance Crouther, Richie Vos, Mario Joyner, Ali Leroy. I know I’m forgetting others. It was a strong strong shop. While I loved it because it was like hanging out at the clubs in the old days, I was incredibly anxious the whole time because I hadn’t been back to this rodeo in ten years. But I thought I was hiding it well.
The night of the show, I’m in a back room with half the writers and I’m on the phone the whole night to Stilson backstage, just feeding lines for Chris from the rest of us. Vos said it looked like I was constantly calling my bookie, which is a beyond perfect description.
Okay, so now we’re close to the end of the show, and the host really doesn’t need any more jokes. Jamie Foxx has just won for Best Actor and he comes on stage, head-shaved, with that tattoo of barbed wire around his skull for his upcoming film, Jarhead. For the first time all evening, I walk backstage because I have a line just for Chris, very inside, just to keep him loose. I go up to him and whisper, “Jamie Foxx’s head looks like it signed a letter of intent to Florida State….” He laughs and puts his hand on my shoulder and says to me, “Is the monkey off your back now?” I started to choke up, and then he walked out to close the show. Nine years later, I still get emotional thinking about that. That. That is why people like him and Dave are stars. Those unseen moments of extreme kindness.
You’re a Harvard grad from Massachusetts, whereas Dave is from the Midwest and attended a state school. Can you talk little bit about your working relationship?
You left out that I’m a Jew and he’s relentlessly goyim…. Dave and I became friends for two reasons: 1) I was a comic and we knew a lot of the same people so we could yak about them and their acts. He didn’t have that with anyone at the show. And 2) I grew up with older brothers and sisters, so my reference points and experience skew 10 years older. I’m 57, he’s 67. Works out perfectly.
As for the relationship, we’re very fond of each other and we have a lot of laughs, but the vast vast majority of our time together is spent as boss and employee. After all these years, I think we can tell the difference between when I’m working for him, when we’re working together or when we’re screwing around.
How has writing for Dave changed over the course of your time with him?
When I first got the job, and to this day it is the only piece of specific advice Dave ever gave me, he said, “Don’t write a joke over four lines. I don’t care how funny it is, but if it’s over four lines it won’t fit on a cue card.” In the 23 years since, everything has compressed. Now, he will rarely do a monologue joke over two lines. And that is pretty much the case for everything else. We’ve gone from 4 minute remotes to 2 minute remotes. We’ve gone from one-minute taped extras to 30 seconds. The delivery system is faster.
One of the coolest comedy moments in recent memory came the day after Johnny Carson’s death, when Dave revealed later in the show that the earlier monologue was comprised entirely of jokes submitted by Carson.
A couple of days before Johnny died, Dave and I were in Dearborn, Michigan. While we’re there, the story comes out that Johnny had been sending in jokes over the years. A reporter asked Dave, “Is it true Johnny Carson has been faxing in jokes to your show?” Dave: “Yes. He’s been very generous.” The reporter, a real wise guy who knows Johnny is gravely ill, then asks, “Do you ever turn them down?” And Dave says, “Yeah. We like to break the man’s heart.”
What, if any, effect has the retirement announcement had on the show, the writers, yourself, or Dave?
I am thrilled that he gets to be the first guy to go out on his own terms. Not even Johnny got to do that. And I am thrilled that those of us who have been here 20 years or more, all the people I love, are going to make it to the end with him.
Finally, the loss of an institution like David Letterman is obviously saddening, but it seems like the best possible successor was chosen; I’ve always considered The Colbert Report the true spiritual successor to the Dave and Conan Late Nights. There’s been much speculation over what the show, and Colbert himself, will become, do you have any thoughts?
I like Stephen a great deal, he is big-time funny, and was just happy the decision was made quickly so I didn’t have to have the discussion about Dave’s successor every week with my dry cleaner, doorman or Talmud study group.
The thing that I find surprising is that people, people who should know better, assume I’ll be working for Stephen, as if it’s like GM getting a new president. The man has his own people and they seem to know what they’re doing. It would be great though if when he dropped the character, it turned out his true personality was a guy who was just a real prick.
In addition to Splitsider, Conor McKeon’s work has appeared in The Onion, McSweeneys Internet Tendency, Mental_Floss, Thought Catalog, Yankee Pot Roast, and CollegeHumor, where he was a staff writer. He can be reached at email@example.com.