I had the chance to participate in a Q & A with Late Night with Conan O'Brien's Brian P. Stack, an alumnus of The Second City.
Daniel Solzman: What advice can you offer to the aspiring comedian/comedy writer? For example, is there anything that would prepare me for Second City?
Brian P. Stack: I'm hesitant to give any specific advice since circumstances and opportunities change so often and in such unpredictable ways, but based on my own experience, if you're interested in working at a place like Second City, the best advice I could give is to do get up and do improv or sketch stuff whenever you can with the kind of people you really love working with.
I would also strongly consider taking some acting classes. I had no formal acting training when I started at Second City (just improv performance experience) and ended up learning a lot of basic acting things the hard way later on--things I really should've been familiar with already.
Also, I would worry less about Second City (or anything else) as your ultimate goal and just treat the work you're doing as an end in itself. I know that's a lot easier said than done (and I was always very obsessed with working at Second City myself someday), but almost all the people I know who worked at Second City were out doing work they loved when they got hired by Second City. They were having a good time with people they got along with, it showed in their work, and Second City noticed them as a result.
I think that what Patton Oswalt said about finding a community of stand-ups that were all on the same wavelength as him is exactly how I feel about improv and sketch stuff. I've never done stand-up in my life, but I related to everything he said about that.
DS: Will the studio move to CA or stay in NYC when Conan takes over Tonight?
BPS: I don't know for sure where the new show wll be done, but I tend to think it may very well move out to LA since that's where The Tonight Show has been done for so long now. I really have no idea what the final decision will be, though.
DS: How does writing for Late Night differ from writing for Second City?
BPS: Well, at Second City, we developed our sketches mostly through improvisation. We would improvise scenes every night after the regular show, and when something seemed to work well, it would be brought back on other nights, new things would be tried, and the improvised scenes would eventually be honed into some kind of set, written sketches. Some sketches we did there were never actually set into final script form, though. For example, I did one scene in Second City ETC with my wife, Miriam, and Neil Flynn in which they played a crazy old couple. Every night, they said completely new crazy things to me just to try and crack me up. One night, Miriam improvised a song on the organ with the words, "I've got the whole wor-rld in my pants!" Without missing a beat, Neil turned to me and said, "That's not far from true." One night, in another scene, he looked out into the "yard" and said, "That badger's still out on the lawn. It's high time HE stopped running our lives!" God, that guy always killed me and he still does. I just wish we saw him more often.
At Late Night, there is certainly an "improvisational" quality to the writing, partly because there are several former improvisers on staff, but mainly because we collaborate with each other a lot and bounce ideas off each other, almost like we're improvising a scene with each other. The way ideas get heightened and expanded sometimes reminds me a lot of working back at Second City.
DS: What did you think of Steve Carell last night? Is that really his last appearance?
BPS: I thought he was hilarious as always. I've been in complete awe of him since I first saw him onstage in Chicago about 15 years ago. And I very much doubt that it was his last appearance here. Conan just made that joke because Steve was pretending to be hurt and angry after Conan punched him.
DS: Any idea who will take over LN when Conan goes to Tonight?
BPS: I have absolutely no idea, sorry.
DS: When will the State of the Union monologue be? Tuesday or Wednesday?
BPS: I think it'll be Wednesday, but sorry, I'm not totally sure.
DS: Thanks again, Brian. So if it is on Wednesday, that's good. It means I can watch it thanks to the way I scheduled my classes this semester.
BPS: I hope this year's "State of the Show" is worthy of your schedule-juggling. I also wish I knew when the hell we were doing it.
DS: What did you think of "Lazy Sunday?"
BPS: I thought it was very funny and very original.
DS: Have you seen the West Coast response from Mark Feuerstein called "Lazy Monday?"
BPS: No, I haven't. I hadn't even heard of that, actually.
DS: Is there any specific book that you would recommend for comedy writing?
BPS: I wish I knew if there were any really good books out there on that subject. There may very well be, but I'm sorry, I really don't know.
Based on my own experience, the best training for comedy writing is watching a lot of comedy (seeing what works, what doesn't, seeing stuff you love yourself that doesn't really "work" with an audience, finding out what makes you laugh and the kind of stuff you'd actually like to write yourself) and, of course, through actually writing. As with performing (and I've heard this from countless stand-ups, musicians, improvisers, and sketch performers), there's simply no substitute for getting up (or sitting down) and actually doing the work. Training can be very helpful, of course, but you learn so much more by actually doing it. As Levon Helm said in "The Last Waltz," "You get up there, get your ass kicked, go wait 'til it heals up, and go back. Eventually, you'll fall right in love with it." He was talking about performing in New York City, but I think what he said applies to performing or writing in general.
DS: What about the format of writing for TV?
BPS: There are a lot of books out there about "How to Write a Sit-Com Spec Script" or whatever, but TV shows tend to vary a lot in terms of the kinds of submissions they ask for from writers. Sit-coms, I believe, usually ask for a sample spec script. I've heard (but I'm not sure about this) that it's best to wite a spec script for a show other than the one you're actually submitting to. For example, if you were submitting to Scrubs, you might write a My Name Is Earl script or vice versa. I'm fairly certain that shows like SNL or MADTV usally ask for a packet of sketches you've written, or in the case of Weekend Update writers, a packet of sample "news" jokes. Our show typically asked for 12 to 15 ideas for the show in short paragraph form. I don't know exactly what The Daily Show,Colbert Report and other shows ask for.
One thing to keep in mind, I think, is not to second guess yourself too much when you're writing ideas. Don't worry so much about other people will like, or what any one specific person or group of people is going to like. I would write the kinds of things you'd like to see yourself if you were watching. You can never please everybody (and comedy is obviously such a subjective thing) so you might as well write what you think is funny yourself. Some people might not go for it, but you probably wouldn't be happy working for them anyway. Some of the funniest writers I know have had miserable experiences around people who just didn't "get" their stuff or had a completely different opinion of what's actually funny.