An Extended Interview with Former ‘Colbert Report’ Head Writer Allison Silverman

In And Here’s the Kicker, Mike Sacks talked to some of the biggest names in comedy writing, including Dick Cavett, David Sedaris and Robert Smigel. Here is the complete and uncut version of his interview with former Late Night with Conan O’Brien, The Daily Show and Colbert Report writer/producer Allison Silverman, with loads of new answers not found in the book.

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 guaranteed them barely under 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 80s, 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 80s and early 90s, by the time I attended Yale, the nightmares and O.C.D. had improved a bit. Most of my attention was focused on school-work, 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 when 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 shifts, 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.


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.

He’s not the brightest chap, this “Stephen Colbert” character.

That’s one of the fun things about him. He is stupid, and yet, every once in a while, he will express some sort of minute knowledge that impresses everyone. He knows exactly how and why car engines work.

But the character is a complete moron when it comes to other matters. For instance, he thought Watership Down, the book about a society of rabbits, was nonfiction. And it very much bothered him that the rabbits were at war.

The irony, of course, is that Stephen — in real life — is one of the smartest people I’ve ever met. He’s brilliant.

One of the impressive things about The Colbert Report is what Stephen manages to do with language—twisting, inverting, and molding it. An example: “This show is not about me. This show is dedicated to you, the heroes… . On this show your voice will be heard, in the form of my voice.” It reminds me of S. J. Perelman’s dense, imploding writing style.

Both Stephen and I really enjoy what can be done with language. Stephen’s background allows him to twist words in a very effective way. He is extremely well-read and he has a ferocious memory — he can pull it off.

We definitely tread that line between being too verbal and just making the jokes funny. It’s like what I was saying before about not becoming too enamored with your own work.

Who coined the word “truthiness” in 2005? The word was so popular that it eventually became Merriam-Webster’s number one Word of the Year for 2006. Here’s the official definition: “Truth that comes from the gut, not books.”

Stephen coined that word, and it actually appeared on our very first show [October 17, 2005]. The show has since coined other words, such as “wikiality,” which is “reality as decided on majority rule,” and “freem,” which was coined by one of our viewers. We used the word visually in our opening, and then someone online decided it meant “freedom” without having to “do” anything — without any responsibility or action.

The show seemed so fully formed right from the beginning; it always had a tremendous amount of confidence. I remember a joke Stephen told the first week about James Brady, who was seriously injured during the Ronald Reagan assassination attempt in 1981. That takes a bit of nerve.

That also happened in the very first show. There was legislation in Florida dealing with the issue of being able to shoot another person in self-defense. James Brady was obviously a critic of this legislation, but Stephen just did not understand why Brady would be against guns. It was the character being brazenly and willfully stupid.

The next day we got a handwritten fax from James Brady that read, “You lily-livered Italian-suited four-eyed Jon Stewart–wannabe. You’ll be crying in your cravat when I’m through. You want a piece of me? DO YOU WANT A PIECE OF ME?”

Brady really enjoyed the joke, which was fantastic.

How did the audience react to something like that?

Better than I imagined. They’re very generous — I think they appreciate the boldness of saying something so wrong as a parody of cable-news blowhards.

The show has a very subversive spirit that I think people enjoy; a lot of viewers wind up participating in the show somehow, whether it’s taking Stephen up on a challenge, or creating ideas for the show completely on their own.

Why do you think that is?

I think a lot of times Stephen is asking the audience to play with him. And it’s very fun to play with Stephen Colbert.

Also, it’s always more fun for the writers when we can interact with the real world. Our first idea for the show was to have a more fictional, sketch-y aspect. But we quickly changed our minds. Stephen’s interactions are real — even if his character isn’t. It’s become almost like a Lazlo Toth–type of situation.

Lazlo Toth was the pseudonym created by Saturday Night Live writer, Don Novello. The character of Lazlo would mail — with ridiculous concerns that he took very seriously — real-life executives, celebrities, and other public figures. He would receive hilarious responses back — some of which were later published in book form.

We wanted to create a similar situation with Stephen’s character on The Colbert Report. It can become confusing, because you’re writing on a lot of different levels. Stephen Colbert is a person who plays himself. So, as a writer, you have to consider what you want the character to say. You also have to figure out what the real Stephen is saying. And how the audience will react to it all. And how the guests will respond. It can be overwhelming.

Has it ever felt too overwhelming?

Sure. Sometimes. I did feel that I had the right experience for this job, having worked at Late Night and at The Daily Show. I felt that The Colbert Report would be an outgrowth of those two influences: the satirical side of The Daily Show combined with the silliness and character-driven aspect of Late Night.

You were combining elements from two shows, but by doing so you weren’t necessarily making it easier for yourself as a writer.

It wasn’t easier, no. It’s like a hall-of-mirrors. And it becomes even more complicated on the “Word” portion of the show. You have to write both the argument and counter-argument, and you have to get jokes out of both.

When the show first started, many humor writers wondered how such a show could sustain itself.

I left Late Night to work on The Colbert Report, and I only did so because I very much trusted Stephen’s abilities. I felt that even if it was a failure, it would have been a smart failure.

David Cross, who plays the Al Franken–type character Russ Leiber on The Colbert Report, thought the show was going to be weekly, not nightly. When he found out, he told us we were insane.

Stephen’s character, who was inspired by the Bill O’Reillys, Sean Hannitys and Lou Dobbses of the world, has since come a long way. The show is a function of this character’s egomania, and I think the show can go wherever that ego goes.

And it tends to work best when that ego goes into the real world. It’s amazing who will play along.

Which leads into my next question: How exactly did you get Henry Kissinger to appear on the “Guitarmageddon” episode in December 2006? Kissinger introduced the challenge between Stephen and the guitarist from the Decemberists, by saying, “Stephen, it’s time to rock.”

A lot of it has to do with the children or grandchildren of these celebrities. In the case of Kissinger, it was a younger member of his family who told him he could have fun on the show — although I’m not so sure he did.

Well, it did look like Kissinger was having fun when he exclaimed, “Crank it up!”

I’m not sure if he was having fun or merely experiencing pure befuddlement.

It surprises me as to who’s not willing to play along with the joke — they mostly seem to be liberals. One example: Massachusetts congressman Barney Frank.

On a show in 2005, Stephen asked Congressman Frank if his weight was bothering his wife. Barney, being a notorious gay man, did not find this amusing. If I remember correctly, his response afterward was to call the show “sub–Three Stooges.”

I wish he liked our show more, but not everyone’s going to love it. And to be fair to Barney Frank, we interviewed him before the show had even debuted — it must have been extremely confusing for him.

I want to talk about the schedule for a late-night talk-show writer. I was shocked when I heard how little time the writers have to create jokes for each show.

We have a few hours in the morning to work on the bulk of the jokes. We have to work quickly.

Can you run down a typical day at The Colbert Report?

A typical day gets pretty hectic — I’m usually there anywhere from eleven to twelve hours.

I arrive around 9:30. Usually, I’ve already gotten some news from the papers and from the news shows. I meet with Rich Dahm, a co-executive producer, and Tom Purcell, the head writer. I meet with Stephen, and then with the rest of the writers and producers. We go back and forth with ideas and jokes, and then the writers retreat into their offices to work on their assignments. We then immediately get the production team working on the footage, graphics, music, and props we think we’ll be needing.

At one o’clock, the writers’ scripts are in, and we begin editing and refining the pieces. There’s a second production meeting, to go over new elements we’ll need and to stop production on the ones that now seem unlikely to make it to air.

The entire script is hopefully finished by around four. We have a rehearsal at around five thirty, maybe a little earlier, and we’re done by around six. We re-write and edit jokes that need to be fixed until around six forty-five. At around seven, the show is shot in front of an audience. We finish about forty-five minutes later, and we then go over the details for the following night’s show.

Is it true that writers work in pairs on The Colbert Report? One writer comes up with the lines as the other acts them out?

No, they both write and act them out. There’s definitely a need to say Stephen’s lines out loud, to hear if they really sound like his character.

You wrote an article for Slate magazine in 2001, and you listed the six types of jokes that writers weren’t allowed to come up with at The Daily Show. One of the examples was to avoid “jokes that will get claps instead of laughs.”

That’s very important, actually. We write so many jokes about the news that sometimes we can move into an area of political statements rather than jokes. Our most important task is to be funny. Everyone who writes for our show wants to be a comedy writer much more than a political commentator. It’s easier to get a clap than a laugh.

Were you in attendance at the infamous White House Correspondents’ Dinner on April 29, 2006, when Stephen gave a speech and managed to upset not only the president but half the D.C. media?*

Yes. A group of writers worked on that speech together. This is the type of material we write every night. It never occurred to me that it would affect the audience so intensely. But what we didn’t take into consideration was who the audience was going to be: politicians and press people.

When we had rehearsed that speech a few hours before, in front of hotel staff, we never had any sense that there might be a problem. So when I witnessed the reaction, I was shocked. Shocked!

I was actually sitting with Stephen’s family. Very close to me were Karl Rove and other insiders. I was in the thick of it.

* Stephen Colbert: “… Wow, what an honor. The White House Correspondents’ dinner. To actually sit here at the same table with my hero George W. Bush — to be this close to the man — I feel like I’m dreaming. Somebody pinch me. You know what? I’m a pretty sound sleeper — that may not be enough. Somebody shoot me in the face. Is he really not here tonight? Dammit. The one guy who could have helped… .”

Did Stephen know how badly he was bombing with his immediate audience?

The speech definitely wasn’t getting a great response. Stephen is a fearless performer. He just kept committing to it, plowing forward. Having once performed myself, I know how difficult an accomplishment that is. It was inspiring.

Did Stephen have any idea the effect he had on the home audience? It was broadcast on C-Span, and immediately became, as they say, an “Internet sensation.”

Not really. Stephen only went up to the dais with the specific purpose of being funny. We had no idea how the speech would be perceived. Even later, when we did find out, we were surprised at the strength of the response. The reaction to that speech was a lesson on how many people wanted a voice of criticism at that moment in time.

Are you tired of being asked what it’s like to be one of the few female comedy writers in television?

I am tired of it.

I hesitated to even bring up the question, truthfully.

Most of the time when it’s brought up, the question isn’t actually about being a woman; it’s really about how poorly male comedy writers are perceived. Usually, people want to know how I survive in a writing room with a dozen men, whom they imagine are bullies and misogynists. That hasn’t been my experience at all. I’ve written with great people. And it is important that women hear that being a female comedy writer doesn’t mean you’re going into battle. Maybe more of them will give it a shot once they know that.

Any more advice?

You have to be patient. You have to give yourself a chance. When you’re first pursuing a job in a field like this, there’s a strong tendency to panic. When I took classes with Del Close, he would challenge all of us to wait — to not make the cheap, easy joke in a scene but to have faith that something funnier and more organic was on the way. It can be that way with a career, too. There are a lot of times when your biggest task is to stay calm and keep working.

You don’t have to write for Plant Physiology magazine.

It’s a journal, Mike. You just want me to pronounce that article title again, don’t you?

Yes, please.

“Association of 70-Kilodalton Heat-Shock Cognate Proteins with Acclimation to Cold.”

Got it: “proteins,” “cold.” Thank you very much.

Thank you.

Mike Sacks is a staff writer at Vanity Fair and the author of And Here’s the Kicker: Conversations with 21 Top Humor Writers on their Craft. His upcoming book of humor writing, Your Wildest Dreams, Within Reason will be released by Tin House Books on March 1st.

An Extended Interview with Former ‘Colbert Report’ […]