What is the biggest challenge in creating an episode of SNL—for which you’ve been the head writer for five seasons?
The hardest part is that a host arrives on Monday, then you have just five days to write an entire comedy show. And you don’t even necessarily know the host’s strengths. So it’s like studying for finals every week. It’s about adapting as quickly as possible. It’s like an emergency room for comedy.
But the writing staff is really good, and I’m the beneficiary of that. And the special effects, props, and wardrobe people don’t get enough credit. You can get a polar bear costume in 12 hours. You’re surrounded by people who make your wildest comedy dreams come true.
Do hosts surprise you?
Sure. And more often than not, it’s a nice surprise. The first time Justin Timberlake hosted was such a joy. He was outstanding, and now he’s such a part of the show. And Jon Hamm [Mad Men’s Don Draper] is hysterical. He’s hosted three times now.
The show has been praised recently for its political satire.
It’s important to be a watchdog for any sort of behavior that deserves comical scorn. I always say my goal is to one day usurp Brian Williams. But honestly, for me, the perfect SNL is 10 to 15 different kinds of funny. Not just political. Even when we audition performers and look at writers’ packets, we’re looking for as many different voices as we can get.
How do you stay healthy in the face of the show’s grueling schedule?
Willful ignorance. I try not to see a doctor. And there’s something about the show that keeps you young. Lorne Michaels [the show’s creator and longtime producer] looks great for his age. Plus, I’m a runner, so that’s a good stress release. I used to run along Lake Michigan. I love Chicago. I miss it like crazy.
Just this fall, the show hired four Chicago sketch and improv standouts from iO and The Second City. So the age-old relationship between Chicago and the show remains, right?
Absolutely. Lorne has respect for Chicago and likes to stop there, and has done so for three or four of the last five years. There’s strong improvisation in Chicago, and it’s great having improvisers around to help you with new ideas.
And people from Chicago wind up taking care of each other. I saw [iO alums] Amy [Poehler] and Tina [Fey] do a two-person show in Chicago before they came to New York. [Chicago-trained comedians] Tina, Rachel [Dratch], and Horatio [Sanz] were heroes of mine in college, and they took good care of me when I came here.
Photograph: Scott Clarke/ESPN
Check back frequently for more reasons to love Chicago.