Inside the Conan Writer’s Room with Brian Stack

Brian Stack honed his skills at Second City in Chicago before being hired as a temporary replacement at Late Night with Conan O’Brien in 1997. Fourteen years later, he still works with the late night legend, having travelled to The Tonight Show and then to TBS with Conan. I asked him what it was like to work to work with Conan O’Brien, what advice he has for aspiring comedy writers and to recall some of his favorite Late Night characters.

What led you to comedy writing?

I kind of fell into it through doing improv. I did improv, at first just for fun, with friends on weekends and at night starting while I was in grad school at University of Wisconsin. And then I continued doing it, just for fun at first, in Chicago, at Improv Olympic with Jazz Freddy and other groups. And then I got hired at Second City and worked there for four years just before being hired at Conan. And a lot of the contacts and people I’ve known as a comedy writer were people I knew originally from the improv community. And most of the people I worked with in Chicago are either in LA or New York now and work as comedy writers.

Did you do a lot of sketch at Second City?

Well, we would develop our sketch shows through improv. We would do an improv set after the show and we would also typically include some purely improvised stuff in the midst of our written show. I was in the touring company for two years, where you travel around, mostly doing scenes that resident companies had developed. But we did do some original stuff too, because we had some guys like Adam McKay there who got us writing our own stuff — he’s obviously a terrific writer and he always had tons of ideas, so we did end up doing some original stuff. And I was in the resident company for two years and that’s where the cast would write the show themselves, and so you’d develop the scenes [through improv] and then set them into scripted form eventually.

Was there a particular sketch or revue from that time that you remember?

There was one sketch that I developed with Neil Flynn, that turned out to be a really fun scene. I played a guy who meets another guy in a bar, and he begins to wonder if the guy is hitting on him, and the guy keeps denying that he is but everything he says makes it seem like he is. And because Neil is such a man’s man, he played it so well. I think my favorite scene to do was with Neil and my wife, Miriam [Tolan], in which they played an old crazy couple and I was trying to buy their house to build a Starbucks, and they would just say completely new crazy things to me. The wait staff would actually come in to watch that scene because it was different every night. Their goal was just to crack me up and they always succeeded. To be honest, I often got a little bored with the written material after a while. I learned while I was at Second City that the repetition of doing the same scenes over and over got a little dull to me.

Were you actively looking for work as a writer or as an actor at that time?

At that time, since I had never worked as a professional writer, I think I was concentrating more on the performance side of things, and doing outside voiceover work and things like that. But when the Conan gig came up it actually seemed in some ways like an extension of what we were doing in Chicago. The thing that I really loved about working at Late Night was that it allowed us to write and perform, and I was so grateful for that opportunity and to work with very like-minded people, some of whom I knew in the Chicago improv scene — Kevin Dorff and Brian McCann. And even Andy Richter had been in some of my improv groups. And Conan himself has a very interesting improv background. Before he became a writer, he had studied at the Groundlings, so the show had a very collaborative improv feel. A lot of my favorite ideas came out of improv and a lot of my favorite ideas that developed at Conan were often accidental and grew from a very playful screw around atmosphere. There were things you would never think of sitting at a computer by yourself. That was my favorite thing about that job.

Do you remember what you submitted to get that job?

The circumstances of my getting hired were very strange. [In 1997] Tommy Blacha, another friend of mine from Chicago, he had broken his leg really badly, in such a way that he actually had to be at home. And so they wanted to bring in a writer for one cycle to kind of help fill in. Some of the guys recommended me. The head writer didn’t know me at all at the time. And I sent in a packet of ideas and they liked it enough to bring me in for that one cycle. And I was fortunate to be able to stay on even after Tommy came back. Conan and the head writer, Jonathan Groff, asked NBC to keep me on because they liked the stuff I was doing, thankfully, so they managed to get an extra writer on staff. It probably helped that I was getting the WGA minimum — Leno had just gotten this huge crazy contract so I probably seemed like a drop in the bucket to them.

What were your pitches that you sent in?

I remember having one idea where they would wheel on — where they captured Poseidon, and he was in a water tank wheeled on stage and they were forcing him to do really humiliating things, like tell jokes. I think they really liked the language I was using in it, things like “Conan, your Hibernian flesh will rot on my trident!” and things like that. It kind of fit the voice of the show. And I think I had another bit about the cue card guys slipping in propaganda into the cue cards — like he had a political agenda and he was trying to get Conan to make political statements by reading the cue cards and slipping in political messages. To be honest, I didn’t love the ideas I did in my packet — I liked the things I did on the show later. And I’m so grateful that they kept me on beyond that first cycle.

So that was your first professional job. What was the process like in the early years?

I was surprised at how at home I felt pretty much immediately, largely because I knew some of the guys. But it really did seem like an extension of the Chicago improv world — there was a lot of bouncing ideas off of each other, very open, experimental. The other thing too that helped me a lot was that, as corny as it sounds, the people at the show — the office staff to the band to the crew were all some of the nicest people I have ever known and many of them are still at the new show.

So it was a very friendly, welcoming environment. There was nothing intimidating about it. And I was a little bit surprised by that. I had this image of it being judgmental — a lot of rejection. It felt very open to brainstorming and you were not afraid to toss out bad ideas — like you weren’t afraid you would lose your job because you tossed out a bad idea. And I found that a lot of the best ideas came out of what seemed like bad ideas at first. Because someone else gets inspired by them or you end up doing something as a joke, as an intentionally horrible idea, and it actually gives someone else a good idea. A lot of fun things came out of almost deliberately bad ideas. Like I remember Brian McCann put a FedEx box on his head in the office and was blessing us as the “Fedex pope.” And that actually became a character on the show, even though he was doing it as an incredibly stupid office prank. And it ended up becoming a pretty beloved character — a white robe, and Chuck Taylors and a Fedex box, and that’s something that nobody would think of in front of their computer.

What are the differences in the process now compared to those early days?

It’s changed quite a bit since the Late Night days, those were much longer hours. You would often be there for 12 or 13 hour days and sometimes I wouldn’t get out of there until 1AM or something. Nowadays we tend to get in a little earlier. We usually go in around 9am and usually leave around 8pm. In the old days, some guys slept in the office because it wasn’t really worth going home. Now, our day, typically, we get in and there is a morning production meeting. And sometimes it’s more of a group effort and sometimes you are working bits with one or two other writers. If you have an idea for a sketch on your own, you’re usually asked to write it up on your own. But some pieces are completely group efforts — like many of our old desk pieces, like “The Year 2000,” we would all toss in jokes. And other things, like character sketches, were written by one or two writers, working on their own.

It sounds like it was very loose. Was there a quota or mandate of what you were expected to produce?

Well, as a sketch writer, not really. There is never really a quota. It’s really a case of hoping that you have something, and sometimes you are really reaching. And some of my favorite things came out of that need. Once we really needed a middle of the show comedy bit for the next day. And the band Slipknot was going to be on the show. So Jon Glaser and Andy Blitz and I came up with this ridiculous idea of a goofy comedy group called the Slipnuts being booked the same night as Slipknot because the booker got confused, and we would come out and pour nuts on the ground and slip on them and then sing about it. And that’s another ridiculous idea that came up probably because we were sleep-deprived and needed something for the next day.

What’s the process after your stuff is pitched? Is there a lot of rewriting?

We write it and then we’ll send stuff back to the head writer, Mike Sweeney, and he’ll suggest a change or two. And then at rehearsal, things change too. Conan, being a brilliant writer, often has some good ideas for improving something or making the end of a sketch punchier. Sometimes he’ll leave something as is. But he’s got very good instincts for what will work, and ways to maybe improve things. He might suggest cutting something or shortening something. So things do often change in rehearsal. There are those things that go in exactly as written and stay that way right up until air. The normal process is for things to get changed, at least somewhat, in rehearsal.

Do writers, if they are playing characters, end up improvising during rehearsal, as part of the process?

Yeah. Like recently, I did the voice of the Watson, the Jeopardy computer, as a voiceover. Conan made a comment and I threw in an ad-lib. We just have that loose feel to it. You can’t always do that, especially if the director is trying to cut to someone, and might not have you on camera, but with stuff from the voiceover booth you can do it. There is an improvisational quality to the show. One time I was playing God and I was walking down the stairs and because I am a little bit clumsy and was wearing sandals, I slipped a little bit and Conan said “God, have you been drinking?” and we ended up having this little discussion about what God was drinking. That was obviously just an improvised thing, but Conan really rolls with it because of his background. I always look forward to things going wrong so we can play with them.

You have worked on Late Night, the Tonight Show, and Conan. Can you talk about the differences between the three shows?

It’s been a really great experience right from the start working with Conan. I do miss a lot of the over the top silly stuff we used to do at Late Night. We are still doing some of that. We do do some. We definitely do a lot more than we did at the Tonight Show. I don’t miss that at all. It always felt too big. No disrespect to the Tonight Show as a franchise, or its history, but it was always too big for my taste — too much of an institution and it carried a lot of baggage as a result. And it often felt like we would get self conscious, like “Can we do this on the Tonight Show?” So the new show has a much more open feel that I really like. It may never be as silly and character-based as Late Night was, but it’s a lot more fun than the Tonight Show to me.

What would your advice be to young comedy writers?

I would say, first of all, whatever background you’re coming from, whether it’s improv or standup or writing exclusively, I would follow what’s fun to you and not necessarily what you think you are supposed to do. I think when you love what you do, as you’re coming up, it shows in your work, and people want to be around you, and work with you because you are clearly having fun. And there’s an infectious energy to that. Whether you are on stage doing standup, or doing improv with a group of people, or whether you’re just writing, I think doing what you think is fun and funny is the best road to take.

Also, if they don’t go for what you find funny, you might not have been happy in that particular place anyway. I remember Andy Richter had a writing job in Chicago once, and they hated all the ideas that would have been loved at Late Night. The same sense of humor that he brought to Late Night later on was completely rejected by this show. And it’s not that Andy’s ideas weren’t funny, it’s that they weren’t funny to those people. Also, I think it’s good to meet people who are on a similar wavelength to you, whether it’s in improv or standup. I remember someone asked Amy Poehler, in an interview “What would your advice be for improvisors who want to be successful in comedy?” and she said, “Don’t plan on making any money or owning anything for ten years, and if you stick with it, and are talented, one of your friends will give you a job.”

And that’s exactly what’s happened for many people I know. When someone gets in the door, they remember the people they loved working with back in Chicago, or wherever. And when something comes up, they recommend them. That’s what happened to me. You can make a lot of things happen on your own too, but it’s so often your relationships you have with other comedians. They’re the ones who tell people who don’t know about you what you’re like and what you can bring to the table. In the improv community in Chicago, Kelly Leonard at Second City, would say “Who’s good out there? Who have you been noticing? Who have you been watching?” and I am sure that’s how they still do it. And if you are around people you relate to, your work is going to be more fun, you’re going to have more fun, and you’re going to get better faster.

Do you have any advice for when you hit that wall and you don’t feel particularly inspired? Do you have any methods for that?

I wish I had some techniques for breaking through it. But when it happens, you just hope someone else is inspired that day. (laughs) I have never been able to force a good idea out of my head. Either the blarney is flowing or it isn’t. The nice thing about having other writers around, you can help with someone else’s idea, or something they say sparks something in you. We all have those days when you’ve just got nothing and you just hope that one of the other writers does. It’s just part of the process. It’s not fun when you hit those walls. But it does make you appreciate it on those days when it’s really flowing.

Are there are any particular sketches that you recall fondly over the years at Conan?

One of my favorite early sketches I wrote, and I think it was one of the reasons they kept me on past that first cycle, was a series of sketches where Amy Poehler played Andy Richter’s little sister, Stacy. She had the headgear and the pigtails. Her performance really made the sketch — not that they were badly written — but she just knocked it out of the park with her performance. Some of the later sketches I loved doing were the Interrupter sketches — I wrote those with Michael Koman who writes on Eagleheart now. And I always used to do this ghost crooner character named Marty Kendall. He would talk like Bing Crosby but all his songs were incredibly racist or misogynistic and it becomes clear that he was murdered even in his own time for his views — they were unacceptable even in the 30s.

And I always loved playing Frankenstein too, even though it was totally non-verbal. Once I forgot that I was dressed as Frankenstein when Walter Cronkite was on the show and I was so bowled over to have this icon there. And I was leaving the makeup room and I said “It’s an honor to have you hear, Sir” and he was just like “Good Lord!” and I completely forgot that what I looked like in full Frankenstein makeup and platform shoes. (pause) It’s probably why he passed away shortly after.

Rachael Mason is an actress and writer living in Brooklyn. She teaches sketch writing at the Upright Citizens Brigade. She also performs regularly with her improv group, Rockhammer and writes for the house UCB sketch team, Gramps.

Inside the Conan Writer’s Room with Brian Stack