The Colbert Report’s First Head Writer Remembers the Show’s Early Days and the Correspondents’ Dinner

On December 18, after ten seasons and over 1,400 episodes, The Colbert Report will come to a close. Allison Silverman was the show’s first co-head writer and eventually its executive producer, working on the show from 2005–2009. She’s credited for coming up with the character-defining idea of having Stephen Colbert come out to the interview desk to greet the guest, as opposed to the other way around, the late-night standard. Mike Sacks, author of two books of interviews with comedy writers, And Here’s the Kicker and Poking a Dead Frog, spoke with Silverman for this as-told-to piece.

The First Episode and Starting Out

I joined The Colbert Report in August 2005, about two months before it went on the air. It was definitely no sure thing. Comedy Central only guaranteed 32 episodes, eight weeks of shows. And I was leaving Late Night With Conan O’Brien, a great writing job that was as secure as things get in comedy. But I was pretty confident that whether or not Colbert Report stayed on the air, it’d be funny and I’d be proud of working on it. That was based on what I thought of Stephen. Though I hadn’t spent much time with Stephen before starting, I knew him a bit at The Daily Show, where I had been a writer, and I had heard about him years earlier, in the mid-1990s, from my friends who told me how supportive and exceptionally open he was to his students taking chances when he was a teacher at Second City. Also, I was getting to be a head writer for the first time, so it felt like it would be worth taking a chance.

The days at The Colbert Report were long, and sometimes every minute was stressful. It was a tough, tough job. I remember when I first accepted the position, Stephen said, “I’m gonna work you like a borrowed mule,” but at the time we were eating hot wings and drinking milkshakes, so I didn’t quite take it in. The show is more written than a lot of other shows. When it started, we had a ton of energy and adrenaline, and we built a show that required all of it. As time went on, we had to figure out a way to make it more manageable and sustainable.

Looking back, those first 32 shows definitely feel slower and more “stick-to-the-script” than what the show became, but some things worked right from the beginning. In the very first episode, you had The Wørd segment already in place. The first Wørd was truthiness, which really established the tone; it was a mission statement for the show. Stephen, the character, introduced himself as someone who didn’t let facts interfere with his vision of the world or his delivery of the news. That was completely Stephen. It was his critique of politics and the press. He understood the show immediately.
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Also on that first episode was a story about gun rights and Florida’s “stand your ground” law. Stephen went after James Brady, criticizing him for being a gun-control advocate. Brady, of course, survived a shot in the head during the [March 30, 1981 assassination] attempt on President Reagan. Even though we were actively trying to set up the character of Stephen as a well-intentioned, poorly informed idiot, going after James Brady our very first night was nerve-racking. It felt like a test of how far we could go. The next day the show got a fax from Brady that said, “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?” I kept that fax and looked at it when I worked on each day’s script. Partly because I suddenly had a comedy crush on James Brady, but also because it meant that the show could go pretty far and people would still be willing to play.

Commitment and the White House Correspondents’ Dinner

In 2006, Stephen gave the speech at the White House Correspondents’ Dinner. I remember Stephen rehearsing in the ballroom hours as the hotel’s workers set out plates and silverware. And they all seemed to like it. They were laughing. They were smiling. We thought everything was going to go great. But when Stephen was performing the actual speech in front of the president and the press, it did not feel great. It was uncomfortable. I was super, super impressed that Stephen pushed through that speech. He took out a couple jokes on the fly, which was unusual for him. He skipped one joke that involved handing the president a kids’ diploma, like the kind you’d get for graduating kindergarten. To me, that meant Stephen knew that there was serious tension in the room. But for anyone who wasn’t involved in the preparation, there was nothing in his demeanor or his performance to suggest that he was aware of, or even cared about, the audience staring him down. He stayed completely in character as the most important people in the country stonewalled him.

There’s a lot about Stephen as a performer that I think comes from his many years of being in theater and, especially, being at Second City. He’s just game. He’s willing to go for it. There are plenty of funny people on TV who, for whatever reason, aren’t willing to try things, even just to give a joke or a premise a shot in rehearsal or at a read. As a performer, Stephen will always go for it — he will always take the big swings — in a way that writers just dream of. He’s not afraid to fail because he kind of likes failing. Stephen used to tell me, “You’ve got to learn to love the bomb.”

One of Stephen’s favorite comedy moments happened when he was at Second City as a performer. A castmate was onstage performing one of the written sketches in the show — one she’d done many times before. The premise was that an overly earnest protest singer announces that her next song is “for the whales.” Then she starts the song and there are no words; it’s just these “eeeeeeee eeeeee” whale noises. But this particular time, the performer had somehow forgotten to say that the song was “for the whales.” She just started making whale noises and the audience was completely baffled. They reacted with total silence. Stephen was backstage with another castmate, watching this happen, and they just fell into each other’s arms laughing. It wasn’t at the performer’s expense; in fact, I think they just loved her at that moment. It was more like an appreciation of how absurd and ridiculous and vulnerable everyone is as a comedy performer. Stephen said that this was a moment when he really dedicated himself to comedy.

Stephen Colbert the Character, the Person

One of the tricky things about the show, especially early on, was figuring out what the honest point of view of the show was, and then how to communicate that through the character of Stephen’s contrasting point of view. When you’re working very quickly on complicated stories, that can get hard. It always reminded me of driving in reverse. Usually, we knew our destination, but we had to drive there super-fast and backwards. Every now and then we would be talking about a big story and someone would say, “Wait a minute, I think our point of view is actually the same as the character Stephen’s point of view.” And then we’d be like, “What happens now? Isn’t the audience going to think we mean the opposite of what the character’s saying, when in fact, this time, we’re in agreement with him?” Moments when it’s all synchronized were particularly tough things to write and to figure out. I tended to want the audience to be clear on exactly where we stood, but often Stephen would say, “Let them wonder.”

There’s a sort of strange, ambiguous line between Real Stephen and Character Stephen. I used to have this secret wish that Stephen would break his contract with Comedy Central to do a different show. Then Comedy Central would turn around and say, “Okay, but we own the character of Stephen Colbert.” Colbert would say, “What character?” And there would be this amazing court case trying to define what parts of Stephen are real and what parts are fiction. (No offense, Comedy Central. I love Amy Schumer.)

Audiences can sense the goodness in Stephen even though he’s playing this aggressive, overly confident character who’s clearly trying to compensate for being extremely dumb. One of the first things we decided about Stephen is that he thinks Watership Down, the novel about bunnies at war, is nonfiction. I always loved hearing the real Stephen’s ideas about the fake Stephen’s stupidity because real Stephen is so ridiculously smart. He has a crazy memory for language. It was pretty normal for a conversation to veer into a Lewis Carroll poem and then straight into some hip-hop that he loves.

I think Stephen is a person who makes very conscious decisions about how he wants to live and how he wants to interact with the world. He really, really tries to be disciplined about keeping to that. He describes his religious faith as “a choice” he makes every day, and I think the idea of actively choosing to be a positive force in situations instead of being more passive about [them] is something that’s with him all the time. His life is very deliberate in how he decides to interact with people and in how to behave.

I think Stephen will be great hosting The Late Show. And maybe, since he’ll be himself, people won’t be so scared of being interviewed by him. I mean, a lot of guests were terrified. In my years backstage at Colbert, I saw many of the country’s most powerful people take far too many trips to the bathroom.