Preston Albert snagged an interview with the well known "Chili" Challis, former staff writer and still contributing writer for NBC’s “Tonight Show with Jay Leno” and standup comedian for 20+ years, ‘Chili’ Challis.

Chili has also written for Pulitzer Prize winning political cartoonist and humorist Mike Peters, and for the national comic strip “Mother Goose and Grimm” as well as other famous stand ups and for the nationally syndicated radio show “The Bob and Tom Show.

Chilli also teaches a much praised workshop in standup called "ChiliMax" with partner Dobe Maxwell.

PA: When did you become a comic? or when did you decide on a career in comedy?

CC: I think I wanted to become a comic the first time I saw a stand up comedian on TV. I was probably ten years old...it grabbed me immediately. I performed my first stand up in the fifth grade. I never really planned on a career in comedy that just happened.
How long did it take before you were comfortable onstage being yourself?
Years. I'm a slow learn. To tell you the truth I guess I'm still adjusting to that, maybe you always are. If you think about it what is really you is always changing so it's hard to say this and only this is me...that's too limiting. As an artist you always change. When you're thru changing you're thru! Somebody else said that but I think it's correct.

PA: You run a workshop with your writing partner, Dobie Maxwell. How did this duo come together? Also, what aspects does this workshop cover? How did you decide to focus on these things? (in other words, complete opportunity for a shamelss plug.)

CC: I can't find it in me to do a shameless plug and I know Dobie wouldn't like it either so let's just tell the story. I first met Dobie on the phone when he was the only guy at the Milwaukee Funny Bone that gave me the correct directions to the club. It was close to show time it was raining and I had just had a long drive. Dobie was the house MC, gave me the directions and we hit it off.
Cut to almost 20 years later...we got together when I called him after my Tonight Show writing stint. I had this wild idea to teach people comedy and comedy writing and to my surprise he was already doing it in Chicago. The rest is history. We set about doing seminars as well as independent classes.

PA: What are some differences between just being a comedy writer and abeing a standup comedian? If you are mainly a writer, what importance does standup play?

CC: Actually if you're a writer in LA stand up plays little importance. Most of the writers on the Tonight Show staff are not stand ups. I was one of only two. Actually they worry about hiring stand ups on staff at NBC because it's a pretty much 9 to 5 job. Comics are use to waaaay different hours.

PA: What advice would you give to new comers to standup?

CC: Experiment and have courage. Get to know yourself and reflect that on stage. Let go of ego so that you are open to learning for an extended period of time (years)..and then experiment some more. Appreciate it all. Never stop evolving and growing.

PA: Who have you written for?

CC: Wow I've written of course for NBC's the Tonight Show with Jay Leno as a staff writer...the national comic strip "Mother Goose and Grimm"...pulitzer prize winning humorist/cartoonist Mike Peters...'Bob and Tom' nationally syndicated radio show...lots of well known comics...Howie Mandel...Gilbert Gottfried...Fred Willard...Arsenio Hall...Sinbad...and a couple of U.S presidents...there's more but you can see I've been diverse.

PA: Do you write for their voice or just write and write and if a joke fits their persona you send it to them?

CC: When you write for somebody you sort of give up yourself. You write for that person's voice and what they can deliver.

PA: How did you land the job writing for the Tonight Show?

CC: I landed the job in the most honest way possible. I wrote my way on the show. I wrote for Leno as a personal writer for years until one day they had an opening and he just out of the blue called me. I'll never forget it.

PA: After you quit the tonight show, what were some obstacles you ran into when you came back to stand up?

CC: Well, I never actually quit. After I took leave I wrote for a long time under a satellite contract with Big Dog Productions while doing other things. I needed a change no doubt. The Tonight Show though it was a dream job and paid great TV money was not the creative outlet I needed. I found that in everything creative you have to have your place. This 'place' has to nurture your creativity. Sitting in an office at NBC was not that place for me. I admire the guys that do that year after year cranking out that disposable comedy crap but that wasn't for me.
I was at heart a comic and needed my element. Freedom!


Do you think it is a good idea for a new comic to avoid contacting A rooms early in their career? Should they wait until they've got some experience under their belt, or just try to get stage time wherever possible?

CC: You should always let people see you in the best light possible. Bookers/agents have great memories if you sucked.

Is it true you never get a second chance to make a first impression?

CC: No, you will get that second chance, you have to believe that...but you must work harder.

When it comes to promo, what are something a comic should do? avoid? not bother with?

CC: Always have a current interesting b/w photo. Sell yourself in that photo. Tell a story if it's only with an expression. Also have a simple eye catching promo sheet. List anything that will set you apart. Make sure it's easy to read. Don't bother with long resumes...make what you've done stand out. Of course one of the most valued piece of promos is an honest recommendation.