Inside the Writer’s Room: Behind the Scenes at 30 Rock with Writer/Producer Kay Cannon

Kay Cannon is a producer and writer on 30 Rock, which just started its fifth season on NBC. A Chicago improviser who successfully made the transition to writing after moving to NYC, she now has the enviable position of spending her days coming up with funny things for Tracy Jordan to say.

I talked with her about her years doing improv in places like Amsterdam and Las Vegas, the all nighter she had to pull in order to get Tina Fey the spec script that got her a job, and what it’s like in the 30 Rock writer’s room.

Rachael Mason: How did you get into comedy?

Kay Cannon: Well, I have a theater degree [from Lewis University in Illinois]. And whenever there were plays at the college I was in, I was always in the comedies. I did Blithe Spirit, Barefoot in the Park, House of Blue Leaves, a whole bunch of them. But I was never really in the dramas. And I think I just don’t have a face for it. I think I kind of have a cartoon-looking face, and it just didn’t go well with the dramas. And that’s when I knew, “I kind of think I can do this.” And then I started taking classes after college at Second City in Chicago. And I wanted to improvise and I loved it. A lot of people go see a show and they fall in love with it. And my first show I ever saw there had Rachel Dratch, and Kevin Dorff and Stephnie Weir and I just remember watching Rachel Dratch and saying “I want to do what she’s doing.” And then from there I just kept with it. And every night I was either interning somewhere, or playing at Comedy Sportz and of course I went to Improv Olympic and I took classes there and performed there. And then I ended up doing Boom Chicago in Amsterdam.

RM: A lot of people who have performed [at Boom Chicago] have gone on to do other things. Can you talk a little about your experience there and how it informed you and your career?

KC: It was a huge learning experience. I was very green. I had just been taking classes at Second City and had just started at Comedy Sportz. And Boom Chicago would come to Chicago and hire people from Chicago and then you would go live in Amsterdam for a year. And, what I learned from that experience was… I failed quite a bit while I was in Boom Chicago. Because you just don’t know what you’re doing. And on top of that you are performing in front of people who don’t speak the language. It’s a different way of performing while you are there. But it’s a kickass 300-seat theater that was selling out and we did 180 TourCo corporate shows throughout the year. It was incredible. I performed in castles and in caves, and in Cyprus and all over the place. I was there for a year. I could have gone longer, but I just wanted to get back to reality on some level.

RM: So you came back and auditioned for Second City and got hired for the mainstage in Vegas. Can you talk about the process of putting up your shows there?

KC: Yeah, Vegas was very different because we didn’t have intermissions. You just had to be fast and funny and keep a Vegas audience’s attention, which was pretty tricky. We found that you couldn’t make fun of gambling, because someone in the audience might have lost 30 grand and gotten a free ticket to our show. There were some things you just couldn’t do. What we ended up doing while we were writing our original show is we would do the first act of our show, and then in the middle of it we would call it the “Half Baked” time and it was a twenty minute period where we would try out new ideas and improvise ideas. So we were sort of tricking the audience into thinking they were just watching improv but we were actually trying to write based off of their reactions and then we would jump back into the rest of the show.

Something so great that came out of Vegas, I was in the cast with Joe Kelly, who writes for How I Met Your Mother, and Jason Sudeikis and Seamus McCarthy, and Holly Walker and myself. And Joe Kelly is a writer and he is a workhorse, and because we didn’t have these improv acts where we could just write through improv, Joe would come to rehearsals with written sketches, like four or five. And it made all of us go, “Oh shit! We need to do that too!” We need to come in writing. And that really changed my idea of writing sketch. Just sit down and write it. It might be shitty but just write it.

RM: So after Vegas, then you moved to LA? In order to audition or to try to get writing jobs?

KC: I went to LA and auditioned for pilots and started to write for myself, because I did not enjoy what I was auditioning for and also I didn’t really feel that I fit in any extreme type of character. I wasn’t pretty enough to be the ingénue, and wasn’t quirky enough to be the character actress and I’m sort of ethnically ambiguous. And I just felt that I needed to write for myself to show people what I can do. So I wrote a sketch show with my girlfriends and then Karen Graci and I wrote a pilot called “Big Foam Finger.” It was a sports show because we are both big sports fans, and then I wrote a spec of the Office and Tina read both of those things. So I had been bicoastal for a year-and-a-half and then 30 Rock happened.

RM: So how did that come about? Did you send your specs to Tina Fey or were they just making the rounds via an agent?

KC: I was in a spec writing class, an eight-week course, and I was in the middle of writing my Office spec. And Tina had read my pilot a year or so before because we are friends. And she liked the pilot a lot and so when 30 Rock came about and she was looking to staff her writers, I actually saw her the week of their final hiring. And we were having dinner and she said, “Do you have a spec? Because you have an original but we need a spec,” and in my mind I knew that I had only written half of the Office spec, but I was like “Yes, Tina, of course I do,” and she said, “Well we are looking to hire staff writers so if you have it, get it in to the producers.” So I said, “Okay, when?” And it was a Monday, and she said by Friday, and I was like, okay, I can do that. And then she called me and said “No, actually by Wednesday.” So I found out on Tuesday that it was due Wednesday.

So I stayed up the entire night writing it. And you’re not just writing it for anyone, but you are writing it for Tina Fey to read, so I felt this incredible amount of pressure and I felt like I was going to puke the entire time. Now when I feel like I’m going to puke the whole time I feel like things are good, it must be a good sign (laughs). I stayed up the entire night and I had my husband at the time read it, and he proofed it, and I had a very good friend in LA, who proofed for a living. She proofed it at like two in the morning her time, and I emailed it at nine in the morning. I emailed it from the airport because I was flying out that day, and got on my plane. And when I got off the plane they had read it and I had a meeting for an interview. It was super crazy. Obviously it worked out, but it was a nutso couple of days. It’s that thing where you decide, I could not do this and I could say, “No, I don’t have it” and I will get another opportunity at some other point. Or you challenge yourself and you say, “I’m going to do this.” This is the opportunity. This is the time. And I’m going to go stay up all night long and hope that this works out.

RM: So you were brought in as a staff writer. What are your responsibilities as a staff writer on 30 Rock?

KC: Every show is different in terms of what the staff writers do. What I love, and will always love, about how they run 30 Rock is that if you have a good idea, regardless of what level you are, they will use it. When you are not writing anything you are definitely the worker bee that’s in the room, but what was great about it was there was a lot of respect for the staff writers and if you had good ideas and you were fun to be around, that’s what they want. They want you to bring your voice into the staff and into the show. On that level, I loved it. I felt like, for me, since it was my first show ever, that first year was really stressful. There were a lot of sleepless nights spent thinking “What am I doing? How am I doing?” The first eight weeks, everything was so new, and in preproduction you are sitting in a room full of people and you are just talking, and talking about your life, and coming up with ideas and pitching ideas and it’s much more casual and laidback. And because I was new to this, I was like “Oh, is this what this is? Cuz this is easy. I can do all this day!” And then of course you get into the writing of it and you’re like “Okay, this is hard.”

I think Tina Fey and Robert Carlock are just the best in the biz and they are just so funny and they are so good at what they do, that the bar is very high. Every day you’ve gotta bring it and that’s something that I learned in that first year. In terms of process, I got a script with Tina in my first year, and as a staff writer you don’t always get scripts, so that was an awesome experience. My first script was “Black Tie” with Paul Reubens in it. It was a great experience because it was such a crazy episode. In terms of 30 Rock it sort of said we are going to do this crazy thing and let’s see if the audience likes it and they did. So it kind of opened up the doors to do whatever we wanted. We could be grounded or we could be as crazy as having Gerhard [Paul Reubens] with tiny little baby hands in a wheel chair being ridiculous and silly. And that was an awesome experience that I will never forget.

RM: People don’t remember now, but 30 Rock was hanging by a string for that first half of that first year so that must have been stressful as well.

KC: Oh yeah. God, I forgot about that. Also there was Studio 60 so there was this weird competition and the fact that it was about the same subject matter on the same network. One time it came up, in fact, while we were rewriting “Black Tie.” The way the show works is everyone in the group comes up with the ideas, and then Robert or Tina decide what storylines they want to do, and someone gets assigned a script and they go off and write the outline and the script and we all as a group rewrite it, all led by Robert.

We were in the rewrite process of “Black Tie” and we were supposed to find out whether we were going to get canceled or not on that day. And they called and we got brought into a room and they had not made a decision yet. We thought it was over and they were like “No, we are going to wait. We are going to see how next week goes.” And then luckily the following week we had a decent rating and so we barely stayed on, and then they picked us up for the second half of the second 13 [episodes]. And that was such a happy, happy day at 30 Rock. We were screaming and high-fiving each other. (laughs) I still think we’ll maybe get canceled next week or something. (laughs)

RM: When you aren’t writing your own episode as a staff writer what are you doing?

KC: You are either in a story room in which you are coming up with future stories to write, or you are in the rewrite room, and that’s pretty intense. Led by Robert Carlock, we rewrite a lot. You are doing a page one rewrite, you are pitching on jokes, you are pitching on areas, or you’re trying to fix problems that are within the story in general. And there’s probably four or five in each room. So you are constantly working on future episodes, or improving the episodes that are about to shoot.

RM: What are the days at 30 Rock like? I hear they are pretty long.

KC: We have really long days. Because there is so much rewriting that goes on and the specific process Robert has. And also because Tina is on the show, and nothing goes through without Tina giving notes on scripts. Or if she’s writing, it takes a little bit longer because she’s acting so you have to wait for her to be done doing that. She has so much going on, it’s amazing what she gets done in a day. But we go pretty late. I have definitely come in and seen the security guard at nine in the morning and then been there till six the next morning, and then come out to go home and sleep for a few hours and the same security guard is seeing me leave and is like “What are you doing?”

RM: Can you talk a little about the process of pitching a story? How do you come up with the idea?

KC: A lot of times over the break, every year, we get assigned to come up with an ideas packet. Robert and Tina know kind of the direction they want each character to go and the room has discussed that, we’ve gone over it and said, “We want Tracy to have this arc so think of ideas that will allow that to happen.” And then since we have a show within a show, and our actors are actually playing actors, there is a lot of “What’s going on out there that celebrities are doing?” and what crazy celebrity thing is happening in real life, which we can then have Tracy or Jenna do. Which is such a luxury because we’ve created characters that can be so bonkers, so it’s not out of the realm for Jenna to go country, or Tracy to want an EGOT, so you start to think of those things and coming up with ideas that way. And of course your own true life stuff that you can bring to the table. We had an episode where Jack Donaghy runs over his mother with a car. And John Riggi, who is an executive producer/writer on the show, that happened to his mother. His niece accidentally hit his mother with a car, so we used it. So then you write these ideas and Robert and Tina read them and they decide which ones they like. We have this huge ideas board where we have ideas from the last five years, and we look at it sometimes and say “OK, let’s have them do that.” And then we have them go in that direction.

RM: Since you come from an improv background and Tina does as well, do you feel like that impacts the way you write or impacts the show?

KC: Well definitely in the first year I felt that I was with a bunch of people who were “writer-writers” –they just wrote and they didn’t perform. And it was myself and Donald Glover who were performers, and we were both staff writers. And that was actually very good for both of us because we could improvise stuff or we just had a different feeling of how we approached it then people who just wrote for a living. And I think they liked it, that we did these different kinds of bits. And I like to think we helped some people come out of their shells. I was so scared my first year, I couldn’t believe I was being paid to write so I thought I should use this ability to improvise to help me and bring a different flavor to the room. And it influences the show in that we do these cutaways and Tina comes from that background and the world itself all comes from this improv world, improv and sketch. Nothing is improvised on our show. People think we are following around Tracy Morgan and writing down whatever he says, but everything is scripted. And Robert Carlock comes from SNL, and he had written sketch, so the fact that Tina and Robert come from there, it sort of gives this sketch tone to the show.

RM: Is there any advice or information you wish you had known before you started this job?

KC: Some very good advice was given to me my first year from John Riggi, and I don’t know if he heard it from someone else before, but it was great. He said, “Every day you go to work with the same ten people and for twelve hours a day you talk about the same topic and every day you have to figure out what your role is in that conversation.” It’s like going to dinner every day and talking about the same thing. The people who don’t have self-awareness, they might end up being loud or annoying and those people don’t realize this is a long process and that you need to be able to read the room. And a lot of people don’t do that and they end up getting fired because they are a pain in the ass to work with. I thought that was such good advice because some days you just need to be quiet and listen, and then some days you need to step up.

And also, regarding pitching, I think when you apologize as you are pitching something and you say [in a quiet voice] “Uh, well, I don’t really, uh…..” and you just hem and haw before you get to the actual pitch, you’re losing people. Even if you do have doubts, which I have done before, you can say, “This is the dumbest thing I’m going to pitch….” So it’s having confidence, but also having self-awareness that maybe what you’re pitching is a little bonkers. But I’ve done that and sometimes that idea is what we’ve done.

RM: Any advice for aspiring comedy writers?

KC: I read a lot of people’s stuff. I don’t think people really take the time to rewrite the work. I think they are so happy when it’s finished, you just want to be done with it. And I understand that. I say give your stuff to five people that you trust and get notes and really listen to their notes. There is a lot of good stuff out there, but there are not enough writing jobs out there for just good stuff. You have to really up your game. And that means really taking the time to rewrite your work.

Photo by Ari Scott.

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 Writer’s Room: Behind the Scenes at 30 Rock […]