Arguably one of the funniest performers around (as well as one of the nicest human beings on the planet), writer Brian Stack has held a position writing for Conan O’Brien for the past sixteen years. After working at Second City, Stack began his television career in the mid-90s, writing and performing on ‘Late Night with Conan O’Brien,’ and moving onto ‘The Tonight Show with Conan O’Brien’ and ultimately TBS’s ‘CONAN.’ During his time, he’s created and played fan favorites of the past and present such as The Interrupter, Ghost Crooner, God, Frankenstein, and more recently, John Galliano’s flamboyantly hysterical brother.
He’s been on anything from ’30 Rock’ to ‘The Office’ and recently spoke with The Smoking Jacket about improv, the mecca that was Chicago and naturally, writing for Conan O’Brien.
The Smoking Jacket: So you started in improv, right?
Brian Stack: Yeah! I started when I was in grad school at the University of Wisconsin. I did my first performance at Ark Theater in Madison, and was there for about two years. Then when I finished I moved back to Chicago, which was my hometown, and started taking classes.
TSJ: You were in with a lot of other big names, no?
BS: It was a crazy time to be in Chicago, Madison too. In my very first improv group I had Chris Farley, who was from Madison, and also Todd Hanson, who has been a writer at the Onion for like twenty years or so. He was nineteen when I met him.
And Chris, by the time I got back to Chicago he was already on a lightning fast track, which he deserved to be on. I’ve got to say that as hilarious as he was in films and stuff I wish more people could have seen him live onstage. He was amazing.
TSJ: I’ve heard someone else say that about him, that he was wonderful on SNL and in films, but on a live improv stage he was phenomenal.
BS: Absolutely. I remember the first time I saw him do the “Matt Foley: Motivational Speaker” sketch, his friend – a priest named Matt Foley – was there. I’ve never seen a person completely devastate a room the way Chris Farley did. It was like watching the Stones in ’72. He was a wonderful guy in many ways; wish we still had him, even as a comedy fan.
But yes, by the time I got to Chicago, it was a crazy time to be there. The people you got to watch and work with were staggering. I saw Farley’s first touring company show in ’88. It was Farley, Colbert, Rosanne Duke, Paul Dinello and a bunch of other big names, all in the touring company. Also I saw Amy Sedaris, Tina Fey, Amy Poehler, Dave Koechner; all these amazing people you got to watch. At the time they were just the local entertainment, but we all thought they were brilliant. It’s funny to look back and think they were just in these little improv basements.
TSJ: It must be crazy looking back to see where you all started.
BS: It was a wonderful time. There were so many different kinds of theaters back in Chicago too. People were very supportive of one another. It meant the world to me when Colbert came out and saw our group ‘Jazz Freddy.’ You had people come out seeing shows who didn’t have to but they were just so supportive. That was one of the best things about the Chicago scene; it was very down to earth in many ways, and not much of a showbiz thing. It was a great place to find your voice. It was also very unlikely that an industry person would be in the audience, even though it did happen occasionally.
TSJ: It’s funny to me then to think that so many people in comedy started in Chicago, a place where no industry people were.
BS: It’s really interesting! Now there’s still great people coming out of Chicago, but I think it’s more spread around the country because of places like UCB in both New York and LA or Improv Olympic here in LA, too. It used to be that people made a pilgrimage to Chicago to study at Second City and hopefully get in the company.
I was lucky enough to be from there. I like to think I’d have had the guts to move there the way Tina, Amy or those guys did, but I don’t know if I would have, to be like “I’m going to do this other thing in a whole new city with no guarantees.” [laughs] I don’t know if I could have done that. That’s so amazing to me.
TSJ: Agreed! To go to a city they’ve often never been to and try for a life they don’t know whether or not will work out.
BS: Exactly, and I have so many friends who did that. A lot of people I worked with came to study at the mecca from other places. I think it’s still the biggest improv scene but you can get Chicago-style training elsewhere. The students are passing on what they learned to a new generation. So the teachings of people like Del Close are continuing to ripple out, even though they don’t learn from them directly anymore.
TSJ: Did you ever give any thought to doing stand up?
BS: I have the highest admiration for stand ups but I couldn’t do it. It’s an incredible art form. I have a lot of friends who do it, and a lot of people here at the show do it and came out of stand up. I could never see myself doing it. The idea of getting onstage with a microphone as Brian Stack was always unimaginable to me. [laughs] I always liked being in an ensemble or a character.
I salute stand up but I feel much more comfortable in character. It takes so much courage to do stand up. It’s funny though because I’ve had stand up friends say improv is harder. I think it just depends on the person.
TSJ: When you were doing improv in Chicago, did you see it going other places?
BS: I think I always thought it’d be wonderful if it led somewhere, but I was doing it never thinking it was going to lead anywhere. A lot of us back then didn’t dare to dream. Some had more confidence than others. I remember Jon Favreau; he always seemed to have eyes down the road more than a lot of us. He was the first improviser I knew who had a pager. I remember thinking who is going to page us? Why do we need that? [laughs] But to his credit, he was right. Obviously it served him very well.
But a lot of us were a little too passive in waiting for things to happen. I guess that was the way our personalities were but luckily it still worked out. Of course, then someone like Tina [Fey], she had so much more drive. I don’t think anyone works as hard as her. She’s so brilliant, yes, but even Amy [Poehler] says no one works harder than Tina. She made a lot of things happen for herself while also being very talented. I have the highest respect for people like that, the ones who bust their asses to make things happen. It’s still mysterious to me. I wish I had more of that.
“I saw Farley’s first touring company show in ’88. It was Farley, Colbert, Rosanne Duke, Paul Dinello and a bunch of other big names, all in the touring company. Also I saw Amy Sedaris, Tina Fey, Amy Poehler, Dave Koechner; all these amazing people you got to watch. At the time they were just the local entertainment, but we all thought they were brilliant.”
TSJ: I’d say it’s still worked out wonderfully for you.
BS: Oh, thanks! I feel very blessed to have worked her for so many years with these people. I try not to take that for granted.
TSJ: Speaking of the show, did you go right from Chicago to ‘Late Night’?
BS: I did! It was a very strange circumstance of how I got ‘Late Night.’ I was working at Second City at the time and Tommy Blacha – one of the funniest guys I’ve ever met – was writing for ‘Late Night’ and had broken his leg really badly. They needed someone to fill in for three months. I sent in some ideas, not thinking I’d get the job. And luckily I did! I thought I was going back to Chicago for three moths but Conan and the head writer at the time, Jonathan Groff, thought I was good. They figured out a way to get me to stay. I’m very grateful to them for that because I was supposed to go back. It was going to be three months and it’s been almost sixteen years. [laughs]
TSJ: That’s amazing! How long had you been performing improv before that?
BS: Well, the first time I performed was early ’87 when I was in grad school. I was like twenty-two and had never had the guts to do it. My friend, Mick Napier, a very well respected director in Chicago, he had an improv group in college and encouraged me to do it but I never did. So If I hadn’t gotten mad at myself for not doing it in college I probably never would have later on. He’s the one who told me about Improv Olympic. I owe him more than I can say.
There’s a wonderful documentary that Mick is in called ‘Second To None,’ which is about the creation of a main stage Second City show in 1996. Mick was the director. It’s such a great time capsule of that time because the main stage cast was Tina Fey, Kevin Dorff, Scott Adsit, Jenna Jolovitz, Rachel Dratch, and Jim Zulevic, who sadly passed away. But it’s so fascinating to see these people back then. Tina, with her short hair talking about how she wants have a career like Dan Castellaneta, where no one knows who she is but everyone thinks she does great work. But she had no idea what was coming. [laughs] It’s amazing to watch that all these years after. Plus it’s great for people who want to know what it takes to put on a show.
TSJ: That sounds fantastic. I’ll have to check that out. So when you were at ‘Late Night,’ were you only writing or were you performing as well?
BS: I was hired as a writer but I think the fact that I came from a performing background really helped. It took a little while because they don’t know exactly what you do. Some of the guys knew me from Chicago and knew I did characters but I gradually built it up. Even though I always loved performing I made sure to keep it gradual. That’s why I love working at Conan. I love performing.
TSJ: I was going to ask that. Since ‘Conan’ is in front of an audience there’s a little aspect of a live performance. But you’ve also been on ’30 Rock’ and ‘The Office’ and more. Do you like the live aspect of ‘Conan’ or doing sitcoms more?
BS: I love the fact that when we do sketches it’s almost like being back in Chicago. But those other performing opportunities are really wonderful, especially when you’re a huge fan like I am with ’30 Rock.’ Just to see how a show like that is shot was really fascinating. As you know, single camera shows are shot like movies so it was really interesting seeing how they did it. But you don’t get that instant feedback. I’m always fascinated by how funny a show like ’30 Rock’ is even without having a crowd there telling them it’s funny.
TSJ: That is true. They have to gauge how an audience will react.
BS: Yeah, they kind of have to rely on their own instincts. And someone like Tina or Robert Carlock and their staff, they’ve obviously got amazing instincts. But you don’t have that feedback of testing your material like we do or in stand up. I do love having that live audience though.
TSJ: Do you like the performing over the writing?
BS: I love them both but I’ve never had the experience of just being on a writing staff. I think I’d miss it terribly if I was just a writer. One of the wonderful things about improv is that it’s writing and performing at the same time. You’re not agonizing over the empty page because you can’t agonize over it. It’s all in the moment. I love that. You can’t second-guess yourself.
I’ve never been a very disciplined writer. [laughs] The immediacy of doing it in the moment is what I’m used to. Sometimes you crash and sometimes it does well!
TSJ: I’ve always been a fan of your sketches in particular. When you’re performing on the show, do you improvise within the sketches with Conan? It often seems like you’re going off script, and it ends up being that much better.
BS: I do! I’m really grateful to him for letting me play around and go off script. The fact that he came from an improv background is also great.
TSJ: He must love going off script then.
BS: He really enjoys when things go off the rails. I remember once I was coming down the stairs at ‘Late Night’ dressed as God. I was wearing sandals and slipped a little bit [laughs]. He’s like, “God, have you been drinking?” We had a conversation about God being drunk. It was really fun! It goes back to that thing that you learned in improv of not treating mistakes as mistakes but treating them as gifts. When something goes wrong it can be an opportunity.
Conan enjoys that as much as I do. And I love that the audience can see when something is spontaneous and they enjoy it. The last thing in the world they want to see is for something to go wrong and you treat it that way. They want to see you have fun with it. I learned that in my early improv days, if something goes wrong it can be the most fun thing of the night.
TSJ: I’d imagine that is ten times more fun than reading off of the cue cards.
BS: Absolutely! I think about some of the things that have gone wrong on our show, they end up becoming some of my favorite memories. Brian McCann shot himself once and he fell and his wig came off. His hair was laying next to his body. [laughs] His body was shaking from laughing. When something is genuine like that, there’s nothing more fun. When it isn’t contrived and the audience knows it wasn’t supposed to happen.
TSJ: ‘Late Night’ sort of redefined the way late night talk shows were seen. You’re your sixteen years writing for Conan, how do you think the shows have changed, if at all?
BS: That’s a really good question. I think we tend to do a little less character-based comedy. We still do some but I think it’s a little more unusual for a character to disrupt the show in the audience.
TSJ: Can I ask why?
BS: I think some of it has to do with how the show has evolved in Conan’s mind and what he wanted to do with the show. I’m grateful for it and for how long we got to do it, and that we still can. But I think he also wanted to start to drive more of the comedy as opposed to being the guy who simply reacts to it. A lot of our early sketches would turn him into the straight man. Understandably, that might get exhausting after a while. But we still do some of it and he’s still game for silly bits. I think this show more than The ‘Tonight Show’ has gravitated back to the silly.
TSJ: I would 100% agree.
BS: The ‘Tonight Show’, as sorry as I am that it went away, I don’t really miss it, to be honest.
TSJ: It kind of seemed like a blessing in disguise to a degree.
BS: It really does feel that way. I always felt the studio was too big, and the show was too big. It was very high profile. Sometimes we’d be like can we do this on the Tonight Show? Can we have a guy in a zebra suit run through on the Tonight Show? I don’t know. [laughs] Being self-conscious like that wasn’t great. So I don’t miss that much. It felt like a weird dream. It also gave us perspective as to what we want to do. And while I miss old aspects of the ‘Late Night’ show I think we’re still doing things we think are funny.
TSJ: Speaking of the new show vs. the ‘Tonight Show’, I know people were saying you couldn’t use old bits; some said you could. I won’t get into it because everyone knows about it but I heard Conan on Pardo’s podcast saying he thought it best to dump everything and write all new material for the new show. For example, The Interrupter. Writing a new sketch for that at ‘Late Night’ was hard enough but now, after building a character list over the years, you have to start from scratch. Was that daunting for you?
BS: It was, but there was a part of me that felt good about it. I didn’t want to push a character too far. So as much as I miss doing The Interrupter or Ghost Crooner, I felt what else could I do with it? There’s a part of me that makes me feel it’s best we can’t do them. I never want anything to get stale.
TSJ: Do you still get to perform outside of the show?
BS: Now and again, yeah. Our hours aren’t as crazy as they used to be so I do occasionally do shows. Plus, with my kids growing up it’s hard to get out. And I’m fine with that. I’m able to help with homework and such. Back in the old days I’d get home like two hours after they’d already been sleeping. I’d get back at eleven, twelve or one most nights and now I’m home by 8. And luckily, since so many of my old Chicago friends are here I’ve been able to do shows.
One of the nice things about LA is that you’ll get these TV and film actors who come to perform. It’s really nice and inspiring to see. They do it out of the pure love of performing. People say it’s just about showbiz and money but these people come and it’s obvious they have their heart in it. They’re not getting paid for it so they must have their heart in it.
TSJ: There are good people in LA, despite what people say.
BS: Yeah! And it’s funny because almost all of my old Chicago friends live here. Everybody is here. It makes it really nice.
TSJ: That must be a cool feeling.
BS: It’s really great! It feels like Chicago West.
TSJ: Was it weird transitioning out west?
BS: A little bit, but I like it. I do miss the fall and stuff but there’s a lot to love out here. Plus, the fact that everyone is here, it makes all the difference. When you’re performing it feels like you’re in Chicago. It’s a great community. There’s a lot more happening on a local theater level than people would expect. It’s a real growing scene.
TSJ: I remember being a script intern at ‘Late Night’ and thinking writing for that show looked so challenging. After all the years, has writing there at all gotten easier?
BS: That’s a good question. I think the ideas come the way they always have. Sometimes they flow and sometimes they don’t. I think it’s a little less time consuming in part because Conan and Andy drive so much of it now. We don’t have to do huge, elaborate desk pieces anymore. We still do some but the number seems to be smaller. So in some ways it’s less time consuming, but the ideas are still a challenge to come by.
TSJ: The turnover for the show is remarkable. You guys write all day, rehearse in the afternoon and then perform around 5:30PM. It really amazes me, the fact that you’re able to do that.
BS: Oh, thank you! I remember Tina Fey quoting Lorne Michaels, saying, “The show doesn’t go on because it’s ready. It goes on because it’s 11:30 on Saturday night.” And that is how we treat it. Even though we have the luxury of a few camera fixes, it’s really true.
In some ways it’s a blessing because you can’t agonize so much. You can’t turn into the most recent Guns N’ Roses album. There’s no way one of our sketches can become ‘Chinese Democracy.’ [laughs] We don’t have the luxury of time, which I think is really good.
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