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Conan O'Brien's Guide To Creativity

Conan O'Brien collage for FC cover

Most Creative People in Business 2011When we visited his office on the Warner Bros. lot for this year's 100 Most Creative People in Business package, Conan O'Brien opened up about how he works. He's an analytical guy. He thinks a lot about the creative process, how to turn a half-baked idea from a morning brainstorm into comedy gold (or a diamond—see below) by the 4:30 p.m. taping of his TBS late-night show.

In addition to our story, a running account of O'Brien putting together a show last month, here he is talking at more length. For all the preparation he does, the best material often comes from going off-script and reacting in the moment. Which is like surfing. We’ll let him explain.

For audio from our Conan interview, click here. But these are his curated comments on creativity:

Creating a show is like playing the horses.

Creativity needs two ingredients, in comedy especially. It needs the sort of relaxing bull shitting, left-brain throwing ideas around where 99 percent of it is a waste of time. But then someone throws out a weird nugget or they're just riffing on something completely inconsequential and they come up with something great. And then the next day is about we're assembling them, we're putting it together. and you'll see rehearsal is really key, because rehearsal is where everything is put up… I can look at some things on paper and say it's going to be great. But you see it on its feet and you just know it's not there. … That's the thing I can't stress enough. In comedy, it's a little bit akin to the, there's the guy that goes down to the racetrack, looks at the horses, talks to the jockey, tastes the soil, measures the humidity. And he may do one percent better than the kooky old lady who shows up and says, "I like the color blue and I’m going to go for Blue Bottle in the fifth."

No, wait—it's really like making of a jewel.

It's almost like when you make a diamond. You need an incredible amount of pressure to turn carbon into a diamond, and I think as you get closer and closer to the show, the pressure increases, and you start running out of time and that's when more and more key decisions are made.

Prepare like crazy so you can wing it.

My formula has always been I'm big on preparing. Prepare like crazy. But then just as you're heading out, half an hour beforehand, forget all of it. It's there. It's in your reptile brain. Go out but feel loose enough to grab opportunities as they come up. Don't just stick to the plan if you see an opportunity. Now sometimes you go out there and the energy is such that you just stick to the plan and you do fine. But when you get out there and the energy is particularly good, I'm the first one to throw out things left and right and just go for it. The show is always best when it's just play. When you're playing, there's a tension, yin-yang tension between think beforehand and then just get out there, between preparation and improvisation. And that's been a lot of my career, finding the balance between those two.

Improvising is like surfing.

I'm very open to when things don't work. That becomes the fun. Obviously, Johnny Carson was really great at that. I've learned to really enjoy that. It's surfing. You don't know exactly how the wave is going to break. You get on it and then you improvise. And I think there's something, it's really inspiring actually, there's something in the human mind that knows when something is organic. That knows when something is happening in the moment. So the audience will laugh at our prepared stuff but whenever things go off the rails and I start shooting from the hip and then maybe going back and forth with Andy or a guest, and we're all shooting from the hip and we're making it up as we go along, the whole energy in the room changes. People know it. They know that this is the real thing. They know that these cookies are being made fresh right there in front of them. And it's exciting.

Creativity should be fun. Seriously.

I used to be very intense at rehearsals. I just found it wasn't helping. So I've tried to learn and say let's keep it light. Let's also not overcook things. Let's try and get things into rough shape. One of the qualities people like about what we're doing is that it can feel very loose. That's the biggest comment I get from everybody on this new show: You look like you've having so much fun. And the truth is you can't fake it. You can fake it a little bit, but you can't fake it day after day.

Fostering a collective comic sensibility is like cooking.

I do sympathize with how the batting average for writing good material is really tough, so at the very least I’m trying to create an atmosphere where failure is inevitable. And where everybody gets to make fun of everybody. Do you know what I mean? I like to screw around with them, try and make them laugh. One of my favorite things is to take out my iPhone and be pretending to read them reviews of the show we just did which all praise O'Brien's ability to rise above the writing. And all these different ways of insulting them. They know it's all a joke…I used to think I need people to marinate—this sounds disgusting—they need to marinate in the essence of Conan. So I make sure that I'm around a lot. I'm just here. I'm roaming the halls… So there's this sense that they can pick up on how I think. Now we've got so many people who have been with me for so long that some of them talk like me. But then there's also when someone comes up with something out of left field that's got a different energy and it's good. It's all of our excitement about that that sends the message that it's good to find those things.

What Conan has learned from CEOs.

The last year has been completely improvised from the time I sent out the ["People of Earth"] statement. And I think it's been one of my better years. I'm learning that not everything is in my control. I heard once years ago, they did a study and they found that really successful CEOs are good at knowing what's in their control and what's not in their control… And I have learned that there are new cycles that good for a show like mine. There are new cycles that bad for a show like mine. There are times when the guests, great guests are coming left and right. There are times when you're really in a flow, things come and go, your opportunities come and go. It rains. There's a drought. It rains. The show is not all coming from me. My job here is just to try and make the adjustments I can make, set a tone.

Conan’s pep talk to the staff.

My people tend to stick with me for a long time, and I tend to stick with them. What I try to tell them especially with this new show is, we've all been through a lot, we went through this tough time and made it through to the other side. There's a sense that it galvanized people here. We stuck together. We kept our heads. We're here, so let's enjoy this. The thing I keep telling them is the only way we can screw this up is by not being bold enough. There is nothing to lose. Let's just if we think of it, and we think it's funny let's just try and make it happen.

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