A lot of people are amazed when you sing on the show with people like Elvis Costello and Willie Nelson. Have you ever had any voice training?
I did choir and things like that when I was in high school. I can tear off the bass line to Mozart's Mass. But my whole family sings. In my family, we could hug each other and kiss each other anytime we wanted for no reason whatsoever, and we were encouraged to sing around the house. My sister Margot and my brother Jay, I'd give anything for their voices. They're such angels, and the rest of us in the family just like belting it out.
Would you all sing carols on Christmas Eve?
Sure, we'd process through the house, and we still do it. My family is 50 people now – nieces and nephews and that sort of thing – and we process from the youngest to the oldest. The youngest puts the baby Jesus in the manger on Christmas Eve, and we sing "Silent Night." It's very traditional.
I heard you were in a Rolling Stones cover band when you were younger.
I had a high school band called Shot in the Dark, and we played a lot of Stones. We weren't really a cover band, but I wore a tight jersey like Mick – a soccer jersey with a number zero on it that said COLBERT across the back. My brother Peter had been number zero. That was his jersey.
Do you believe the theory that the youngest sibling tends to clamor for the most attention and generally ends up becoming more of a performer?
Oh, sure, I had a built-in audience for that. I think my brothers and sisters are way funnier than I am – and they think they're funnier than I am too. Ask them, and they'll tell you. I wanted to tell stories like Ed, tell jokes like Billy, have a rapier wit like Jim, be quick like Mary or sing like Margot. Being the youngest, I caught my mother saying to them once, "Listen to his stories – you listen to what he has to say." To this day, if an audience likes what I'm saying when I'm telling a story, I think that my mom got to them, and she's making them listen.
Did you ever go through a period where you lost your faith?
Yeah. It was a college angst thing. But once I graduated from college, some Gideon literally gave me a box of The New Testament, Psalms and Proverbs on the street in Chicago. I took one and opened it right away to Matthew, Chapter 5, which is the opening of the Sermon on the Mount. That whole chapter is essentially about not worrying. I didn't read it – it spoke to me, and it was an effortless absorption of the idea. Nothing came to me in a thunderbolt, but I thought to myself, "I'd be dumb not to re-examine this."
What caused you to go through that dark period?
Well, I had very sad events in my childhood. The death of my father and my brothers was understandably a shattering experience that I hadn't really dealt with in any way. And there comes a time when you're psychologically able to do so. I still don't like talking about it. It still is too fresh.
Do you think experiencing that has helped what you do in any way? Or made it more of a challenge?
Not to get too deep here, but the most valuable thing I can think of is to be grateful for suffering. That is a sublime feeling, and completely inexplicable and illogical, but no one doesn't suffer. So the degree to which you can be aware of your own humanity is the degree to which you can accept, with open eyes, your suffering. To be grateful for your suffering is to be grateful for your humanity, because what else are you going to do – say, "No, thanks"? It's there. "Smile and accept," said Mother Teresa. And she was talking to people who had it rough. That's not how you make jokes, though.
Getting back to jokes, do you think Bush was a better president for your comedy?
President Bush was an excellent model of incurious authority. But for the last year and a half of his presidency, I almost never mentioned him, because everything that could be said had been said. Satire usually exists in opposition to power or as commentary on power, and Bush stopped being powerful way before he left office. So for the last 18 months to two years of the Bush presidency, he stopped being my model, and we returned to the core principle. And the core principle is that I'm a well-intentioned, poorly informed, high-status idiot – and that exists whether Bush is in the White House or Obama is there.
So in a way, is Obama better for your character because there's more for him to be outraged by?
I'm having a great time with Obama. In some ways, it's a more freeing game, because not all things are known about him yet. The page is still being written on him, and the common ignorances about him are emerging. Socialism was a good one for a while; now that's a little played out. Or the Birther thing, about him not being born in the United States – who could have made that up? I don't exist in relationship to the president. I exist in relationship to common ignorances, and those will never go away.
When you went to the White House to film Obama for your Iraq trip, what was it like to have the president of the country play along with one of your skits?
It was hard for me to conceive that I was going to the White House to actually do a bit with the president of the United States that we had written for him. Matter of fact, I wasn't going to go. I thought, "If I leave, I won't be able to get any writing done that day."
I think Obama crushed it. We did two takes, but we used the first take. It was surreal and wonderful, and I hope I get to do something like that with whomever the next president is. It was a great joy and a great honor, the same way it was an honor to do the White House Correspondents' Dinner when Bush was president.
Why do you think your appearance at the dinner became such a scandal?
I had no perception that anything was wrong at the time. When I was doing the Correspondents' Dinner, I was specifically making an equation between myself and President Bush. If you look at the opening of it, I wasn't up there as O'Reilly. I was up there as Bush, and that was the whole idea.
Right after the dinner was over, something felt weird, because people weren't making eye contact with me. But it was a few days until someone made me go online and said, "You should look at this." I had no perception that people thought I was throwing Molotov cocktails. I just went and did a job, and I thought I did a good job, and I wish more people had laughed. That's all I feel about it.
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