And Here's the Kicker: Conversations with 21 Top Humor Writers on Their Craft

by Mike Sacks

  Where do you think Mad will be in twenty-five to fifty years?

  You know, with technology going the way it is, who knows if there will be magazines in the next twenty years — or newspapers for that matter.

  How about the future for comic-book illustrators? For a humor writer, one would assume there will always be television or the movies. But illustrating for a comic book like Mad seems so specific a talent. Do you think it will survive?

  I think there are going to be some drastic changes as far as commercial artists are concerned. Even as you were speaking, I was picturing getting up in the morning and a favorite comic strip is on a panel and it rolls by and it's animated. No longer will it be “Peanuts,” with four panels and static little figures. Now it will feature characters walking or kicking a football right in front of you — all on a sheet of something that is no bigger than a page. All of that is bound to come. Truthfully, I don't know what we're going to gain or what we're going to lose. Of course, you both gain and lose from the advance of knowledge and technology.

  You've been at Mad longer than any other writer or artist. You've been published in more than four-hundred issues. And yet you said something recently that I found intriguing: “If I were fired tomorrow from Mad, I think the old creative juices, the old inventions, would surge.” My question is how much more do they need to surge? You're still going strong.

  I'm taking the easy path now. I'm doing things that are available to me, rather than going out and inventing new things and proposing them, because I just don't have the energy to become a salesman for these ideas. I find it really satisfies my creative instincts to do just a fold-in once a month. I think the fold-in is my last hurrah.

  Will you be willing to give me a snappy answer to a stupid question? How do you think you'll be remembered?

  Is space available on Mount Rushmore?

  Maybe I should leave the last line blank so the readers can fill in the answer for themselves?

  Sounds good. Do it.

  Famous Last Words (of Advice)

  Don't concentrate on becoming a better humor writer, just concentrate on being the best writer that you can become. If you're funny, the work will end up being funny. And if you're not funny, the work will still end up being good. Concentrate on being the most honest writer you can be, and let everything else follow — because it will.

  — John Hodgman, The Areas of My Expertise

  Allison Silverman

  It's difficult to know just how seriously Allison Silverman takes herself, or her place, in the hierarchy of comedy-writing. Having spent time penning jokes for some of the best minds in satire — Jon Stewart, Stephen Colbert, Conan O'Brien — she'd be justified in some self-aggrandizement.

  “Over the course of the week [at Late Night with Conan O'Brien],” she once said, “[my desk] becomes a dumping ground for scripts, daily schedules, weekly schedules, cast lists, revised cast lists, and beat sheets. A beat sheet lists the comedy bits approved by our head writer. A beat sheet is how the wardrobe department finds out that we need a giant Hasidic ant costume by two P.M.” For Silverman, comedy is just another way to pay the bills, albeit a means of employment that occasionally involves dressing up actors as Semitic insects.

  Long before she became one of the most influential female writers in TV comedy, Silverman was just another lanky Jewish girl growing up among tanned goyim in Gainesville, Florida. Though she briefly considering becoming a scientist, she eventually ended up majoring in humanities at Yale University. After graduating in 1994, she moved to Chicago to study with such comedy institutions as ImprovOlympic and The Second City Conservatory, the alma mater of future employer Stephen Colbert. During her graduation show at the Second City in 1996, she performed an original song called “These Are My Gandhi Years,” in which she sang about the trials of being poor and underfed as a struggling artist.

  A year spent improvising with the Boom Chicago comedy troupe in Amsterdam (1997) was enough to convince her that she preferred the desktop to the stage. She wrote trivia — cooking up amusing minutiae for the ABC quiz show Who Wants To Be a Millionaire (1999) and the computer game You Don't Know Jack (2000) — before finally mustering the courage to cold-call Daily Show head writer Ben Karlin and ask for a job.

  It was a gutsy move, especially in an industry where female writers are about as common as conservatives. But her perseverance paid off. Her groundbreaking year at The Daily Show led to a four-year run writing for Late Night with Conan O'Brien (2002–2005), for which she won a Writers Guild award.

  Then she did what few comedy writers in her place would have dared: she made a major career gamble, leaving a dependable writing post at Late Night to write for The Colbert Report, hosted by her one-time Daily Show colleague Stephen Colbert. Comedy Central promised only thirty-two episodes, which gave them just barely two months to prove their comedic chops and attract a loyal audience.

  The Colbert Report was originally envisioned as a spoof of the pomposity and the garishness of The O'Reilly Factor. If they had stuck to that premise, the show most likely would have ended the moment the novelty wore off. But Colbert and Silverman transformed a simplistic, one-joke news parody into one of the most subversive shows on TV, even surpassing The Daily Show with its satiric verve. Whether he was yammering on about “truthiness,” having water playfully thrown in his face by billionaire Richard Branson, or mocking President Bush at the 2006 White House Correspondents' Dinner, Stephen Colbert (the character) was a walking-and-talking indictment of arch-conservative egotism. The right-wing pundit was the fake-news personality that everybody (sometimes even Republicans) loved to hate.

  Silverman, who has been The Colbert Report's co–head writer with Richard Dahm since 2005 and a co-executive producer since September 2007, is largely responsible for much of Colbert's fictional persona — including the idea for Colbert to strut around his desk as guests make their entrance over to the desk.

  “That was my idea,” Silverman said. “For me, it felt like a strong statement of ego: that Stephen would be jealous of even that tiniest moment when his guests would be in the spotlight. So he diverts all of the attention — to himself.”

  You're one of only two humor writers I'm interviewing from the South — the other is David Sedaris. My southern friends and teachers aren't going to be too happy.

  I grew up in Gainesville, Florida, which is a university town. But, yes, it's very much the Deep South. When I was growing up, I never looked similar to my classmates — or that's how I felt, anyway.

  What did the others look like?

  It was mostly an environment of blonde cheerleaders, football players, and quintessential Americana. When I was young, I received a lot of questions about where I was from. I remember being told I would eventually be going to hell because I was a Jew. This was mostly in elementary school, before the students realized what they were saying. But by the time I was in high school, fellow students found my Semitism a little exotic.

  Do you think your upbringing affected your humor? Did you go inward and become more introspective?

  I guess I felt like a bit of an outsider, but I don't think that's too different from how most humor writers feel about their childhoods. I was an introspective person by nature. I was a happy kid, but I did have terrible nightmares. I'd turn on the bedroom lights and spend the rest of the night reading — usually the same few books over and over again. I must have read A Wrinkle in Time [by Madeleine L'Engle] fifty times.

  Do you remember any of your nightmares?

  Dreams about nuclear war, mostly. This was in the early eighties, and I had just learned that Gainesville was high on the list of nuclear targets, because there were a lot of hospitals in town. I also remember a classmate telling me about the nuclear explosions in Hiroshima and Nagasaki, and how the shadows of the victims were forever burned onto the pavement.

  I also had many dreams about being poisoned, and my accidentally poisoning others.

  [Laughs] What type of kids were
you hanging out with?

  I can't blame it all on them — I think I had O.C.D. as a kid. I would have recurring thoughts that were mostly uncomfortable to think about.

  That's another similarity between you and David Sedaris — and perhaps most of the writers I've interviewed for this book. O.C.D. is a very common theme.

  Starting at around the age of nine or ten, I would suddenly feel the urge to stick to a very strict routine. I had to do all these very specific tasks before I felt comfortable enough to do much of anything.

  I was obsessed with death and with order. My mother once showed me a biography of Albert Einstein and told me that he didn't wear socks. And she said, “See? This is one of the greatest minds of all time. And he didn't wear socks! He wasn't perfect, so you don't have to be either.”

  Did that help?

  I remember it, so it had some kind of impact.

  Do you think this preoccupation with death was a Jewish trait?

  I think it might have been, actually. With Judaism, there's very little discussion of the afterlife. I was told that I wouldn't die for a very long time, but then once I did, there would be nothing.

  Did this preoccupation ever ease up?

  In the late eighties and early nineties, by the time I attended Yale, the nightmares and O.C.D. had improved a bit. Most of my attention was focused on schoolwork, and on an improv group I was involved with called the Exit Players. There were about four improv groups at Yale, but this one was the oldest, and still is.

  How did the Exit Players differ from the other groups?

  I thought they were the flat-out funniest. There was another group that performed long-form material, but I didn't really understand that method until after I graduated.

  In retrospect, I prefer long-form. But, at the time, short-form was my preference.

  What's the difference between short-and long-form?

  Long-form improv was most famously taught by [Second City's] Del Close through his “Harold” method — that's what he called it. Essentially, a group of performers receive one suggestion from the audience and then create a whole piece around that subject. There are three acts, each with three scenes. This method teaches that you shouldn't go for the immediate and easy punchlines. Short-form, on the other hand, consists of more gags.

  Is this something you'd recommend for humor writers — to start with improv comedy?

  Absolutely. I think there are a few reasons why it's a great idea. One is simply that you learn timing — what does and doesn't work with audiences. If you've never experienced an audience in this specific way, it's more difficult to learn later on.

  It also helps — if you are going to write for somebody else, like I have for Conan, Jon, and Stephen — to understand the needs of a performer. Sometimes writers become very enamored with their own material — especially those who write for print. But what is very, very funny on the page might not work before an audience. The material might be too difficult for the performer and for the audience to follow. Get rid of all the verbiage, and refine your way to the core of the joke.

  Third, I think it's vital that comedy writers don't hole themselves up and work alone. They need to meet and have a community of like-minded people — some of whom might hire you down the line. It is much easier to create this community if you're performing.

  Do you get the same high writing that you used to achieve while performing?

  It's a different high. I love being backstage and watching one of my jokes really hit. It's the grace of being an anonymous donor, only better. My name is on the credits. It's the best of both worlds.

  Did you receive a drama degree from Yale?

  I was a humanities major, but it's been mentioned by a few journalists that I was a molecular-biology major — which I definitely was not.

  I read that, too. I was very impressed.

  I said at some point that I matriculated as a molecular-biology major, but that just means that I started Yale as one. Once I was there, I got much more into the humanities. I do love science, though. I worked in a lab for several summers and got my name on a paper in the journal Plant Physiology. The paper is called “Association of 70-Kilodalton Heat-Shock Cognate Proteins with Acclimation to Cold.”

  I only understood two words: “proteins” and “cold.”

  It was about finding the genetic basis for cold-tolerance in plants. I performed experiments with the help and direction of people who really knew what they were doing. They were very kind, and they put my name on the paper as a co-author.

  Did you approach humor with a scientific eye?

  Actually, I did. When I lived in Chicago after college, I would watch the Second City performances, and I would take notes on the performers and on their individual moves.

  What sort of moves?

  I'd make notes about how each performer responded to their onstage partner. Status informs all humor. Specifically, a lot of comedy is about status shift s, and I would mark down whenever a shift would occur.

  A “status shift” is about who controls the power in a scene. You see this in real life all the time. You see it with parents and kids; the parents are obviously in control, because they're older and bigger, but when the kid throws a tantrum, the parents try to placate the child by giving them something.

  Now the kid is in control. That's a status shift.

  So what does that mean within the context of a sketch?

  I'll give you an example: John Cleese would often play characters who were in charge but shouldn't have been. A lot of what makes his characters so funny is that they are completely unfit to lead. In the Monty Python “Kilimanjaro Expedition” sketch, he's leading an expedition to climb Kilimanjaro, but he has double vision and thinks Kilimanjaro has two peaks.

  It's not funny to see someone powerless being mocked. I think most people react against that, actually — unless they are a particularly cruel audience. What's much more fun is to see someone who does have power, and is in the dominant position, become exposed.

  So that's the power structure. When you twist and play with this structure onstage, it hopefully becomes interesting and, in the end, funny.

  Can you give me a specific example of how status came into play with any of the television shows you've written for?

  I once wrote a sketch on Late Night with Conan O'Brien that I liked because it dealt with some issues that were on my mind at the time.

  The sketch started with Conan returning from a commercial break and saying something to the effect of, “I've got to tell you, sometimes being a talk show host makes me feel a little guilty. I could have been a lawyer or a doctor — that would have been way more valuable to society.”

  There was an actor in the audience who piped up, “Excuse me, Conan. I am a doctor, and I just wanted to let you know that you couldn't have become a doctor, so just stop worrying about it. You just don't have the skills to be a doctor — or the intellect!” The “doctor” then injures an audience member and demands that Conan prove that he actually could have been a physician. Conan manages to treat this “patient” brilliantly.

  It starts with a switch: At first, Conan is in charge and says, “I could have been a doctor.” The doctor says, “No, actually, I am in charge, and you couldn't have become a doctor even if you'd wanted to.” And then it switches once again.

  You just mentioned that you liked this sketch because it dealt with some issues on your mind at the time. What in particular?

  Certainly anyone who's a comedy writer thinks — at least on some level — that maybe they should be doing something more “real.” I still feel that way, truthfully.

  Really?

  I always think I should be doing something that should more directly affect the lives of others in a more positive way.

  You don't think your work on Late Night, The Daily Show, and The Colbert Report has affected people in positive ways?

  I am exceedingly thrilled when people tell me those shows make them happy, but I don't think it's
the same as dedicating one's life to bringing more knowledge to the world. Or being a social worker and directly helping people. Or being a teacher.

  I'd hate to see where I'd fall: a writer interviewing humor writers.

  Clearly, we should both be determining how plants tolerate cold.

  One could argue, however, that you are bringing knowledge to the world. As you've no doubt heard a million times, many viewers only get their news through The Daily Show and The Colbert Report.

  I appreciate people who might feel that way, but I think they should also be watching other shows and reading the papers.

  We were talking earlier about status in regard to humor. The character of Stephen Colbert is very much about status.

  Oh, absolutely. Stephen is all about status and the trappings of power. This is a character who looks to be in charge, and he constantly feels threatened by people who have much less than he has. There's a real vulnerability buried deep within that character. His ego is a high-wire act.

  One important thing about Stephen's character is that while he's a moron, he's not an asshole. There is an essential innocence to his character. He's well intentioned, but poorly informed. And because of this vulnerability, the audience comes to accept him.

  It also helps that the real Stephen is a genuinely kind person. Even when he plays this character, the audience still detects that Stephen's a good-hearted guy. That's a major factor with our show: if Stephen couldn't pull that off, the show wouldn't be nearly as successful as it is.

  Could this have been the problem with other, less successful, talk-show hosts? They didn't come across as likeable?

  I'd say so, yes.

  I think it's very important for any host or performer to not battle an audience but, rather, to become partners with them. As soon as you look needy or uncomfortable, the audience becomes worried and stops laughing — which is a big problem. Going out onstage and thinking of the audience as an enemy only makes you look more needy.