Brian Kiley is one of the smartest comedy writers in the country. He has appeared on The Tonight Show with Jay Leno and Late Night with Conan O'Brien, where he has been a staff writer from day one and has been nominated for seven Emmy Awards. He has also appeared on Late Night with David Letterman and Evening at the Improv.

When did you first realize that you were uniquely funny?

In elementary school when a kid would make a joke and someone else would say, “That sounds like a Kiley joke.”

Who do you think were your influences?

Woody Allen, Rodney Dangerfield, Bob Newhart, Steve Wright, my older brother Paul, my Aunt Essie.

Do you remember your first original joke?

When I was four years old, my Mom was driving down California Street and I said to my older brother, “I almost got a sunburn on California Street” and my family laughed. I remember thinking, “That's a keeper.”

When did you realize that comedy was something that you had to do for a living?

When I was thirteen I realized I wasn't going to make it to the Red Sox or the NFL. I decided I wanted to be a comedian or a comedy writer like Rob Petrie on The Dick Van Dyke Show.

What was your first job in comedy writing or performance?

I took a class at Emerson College during the summer taught by Denis Leary. For the final class, we had to do stand-up in front of invited guests. A working comic named Andrea Eisenberg told me that I should pursue this as a career. (She may have been kidding.)

What is the biggest difficulty you've encountered being a comedy writer?

If as a stand-up you come up with a great joke about Michael Jackson, you can do it for twenty years. As a comedy writer, the show does it once and it's gone. The next day the host wants another great Michael Jackson joke. The hard part is writing your 200th Michael Jackson joke. Going to the same well every day is the hardest part.

Are there jokes that you do just for you?

The jokes I do for me, I do in the car to myself on the way to the gig. I can stay home and entertain myself — the job is to entertain other people. I only do jokes I think other people will like.

How did you prepare for your job writing Conan O'Brien's monologue jokes?

I used to do a lot of topical jokes in my act, so reading the papers every day and trying to find what's funny in the news and then trying those jokes on stage gave me a good sense of what crowds will laugh at and not laugh at. Jokes about tragedies may be funny to you or to other comics but they're not funny to normal crowds.

What's it like working on a daily deadline? What's your daily routine like?

It's fun and it's exciting but it's also a lot of pressure. You have to produce every day. If you don't, your jokes fall flat on national television. I read about five papers (ignoring the tragic stuff) and I go to several different news sites on the Internet. I work on my own, brainstorm with another guy, type up my stuff, compile it with the other writers, then we give our stuff to Conan. He tells us what he likes and what he wants more of. We write more, he picks 'em, we tweak 'em, and he does the show.

What are the differences between writing for yourself and writing for others?

Writing for yourself you get to make all the decisions. If you like a joke you write, you do it. I'm lucky in that my “voice” isn't too different from Conan's. Generally, if I write a joke I really like, he usually likes it too and does it. But when you're a stand-up you get the laughs. It's more gratifying than someone else getting the laughs on something you wrote. The highs are higher writing for yourself, but the lows are lower.

What do you find exciting about comedy right now?

It seems that more basic cable networks are making an effort to produce shows. I'm hoping that means more opportunities for comedy. The reality thing seems to be waning, thank God.

Where do you think the future of comedy is headed?

I wish I knew.

As audiences become more specific and more segmented, is your job becoming easier or more difficult?

I don't really notice a difference in the audiences.

What is the best thing about being a comedy writer?

Working with a bunch of people who make me laugh.

Do you have any advice for up-and-coming comedy writers?

Find your own voice, write every day, lose the rap song bit.