Josh Lieb describes the struggles and joys of keeping daily political comedy fresh, making Obama funny, and working with the creative minds in the writer’s room.

Question: How did the Daily Show adapt to the transition from Obama to Bush?

Josh Lieb: Political comedy is just as easy now as it was during the Bush years. It is still – it’s a different cast of characters, but they’ve got all the same foibles. Personally, speaking for myself, I certainly like and trust our President now more than I did our previous one, but he makes plenty of goofs. I certainly don’t approve of everything he does and there’s a cast of characters in Washington right now that are absolutely as hilarious as anyone who was there during the Bush years.

Question: How do you keep the show fresh?

Josh Lieb: We’re always looking to keep it fresh. And that’s not so much because we are scared we’re going to lose the audience, it’s more we don’t want to lose our own interest. You can do the show four days a week, however many weeks a year; you can get bored by doing it. So, we have to keep making it exciting for ourselves. So, there’s absolutely, there is that and then its like, let’s try something new even though it might hard, and there’s also – it’s a group of very competitive funny people and we like to make each other laugh. So, we know what a standard show could be and we are always trying to break out of that just so we can impress each other.

Question: Did you miss the collaborative process of TV writing while doing your book?

Josh Lieb: Absolutely not. No. The hardest part for me in a work environment is collaboration. That is just a struggle that I’ve always had. And I love my coworkers and I love bouncing ideas around with them, but I really enjoyed pure writing. Just sitting and writing by myself. And every show is different. This is the most collaborative environment I’ve ever been in. I used to write another TV show called News Radio where it was very different. We didn’t have any sort of big table or anything where ideas were bounced around. You’d come with a script idea and you’d go off and write it and you’d hand it to the next guy up the food chain and he would re-write it. It was as pure a writing experience as you can get in the TV world.

Question: What is the difference between writing for the Simpsons and The Daily Show?

Josh Lieb: The main difference between the two is just the immediacy. The Daily Show, the New Hits, and we get to take care of it that night. The Simpson’s is such a strange animal, and a wonderful animal, but a strange one. You would be writing for something that wouldn’t air for nine months to a year. And still people would go, wow, how did you get that reference so quickly and frequently it would seem like the show was fresh. I enjoyed the Simpson’s, but I like the immediacy of the Daily Show more. It’s frustrating to write something and then not see the finished product for a year. With the Daily Show, it’s like you are really putting on a show. You know, I’m Mickey Rooney, I’m writing a script, and that night it goes live. And if it’s terrible, we’ll do another show tomorrow night.

Question: How do you manage comedy writers?

Josh Lieb: Oh absolutely. We’re not so different from everybody else. It’s not that I’m particularly funny in this interview anyway; we don’t always have to be funny. How’s that. I think we can be just as adequate at managing people as others can. And it’s all management skills that go into our wheelhouse. It’s okay, I read a script, and this isn’t funny. This is what you need to do. Boop, boop, boop. If I were an accountant I would be able to point out where the number didn’t add up. If I’m watching a montage and this doesn’t go together quite right, as someone who is a comedy professional, I can point out what is going to work better.

Question: Are there other challenges in managing creative people?

Josh Lieb: No. I’ll tell you what; everyone at the show is so nice and so shockingly competent that it’s not a real problem. I’ve been in situations where there have been people who were difficult, or just people you didn’t want to be around and people you had to manage more heavily. There’s nothing like that there. I think a lot of it has to do with the fact that it’s such a fast-moving machine. Anyone who acts as any sort of sand in the gears gets spit out pretty quickly.

Recorded on:   October 9, 2009