INTERESTED IN A SPECIFIC CAREER? Search our full database
Kimmy Gatewood
New York City, New York
Written By: Paul Maniaci
Posted: 08/27/2006

I reached out to Kimmy Gatewood because I knew she would be honest, entertaining, and provide the inside scoop on the challenges of becoming a comedian. We sat down at a small coffee shop in downtown New York City and she dazzled me with her ability to cram as much as humanly possible into a twenty-four hour period with her various projects from improvising, directing a play, and hosting events.

*This interview contains explicit language.*

CCB: Did your sixth grade play Little Luncheonette of Terror spark your initial interest in performing?

KG: I auditioned and ended up getting a chorus part, singing one line. (Singing), “You may think his cooking’s plain.” It’s a rip-off of Little Shop of Horrors about Pete’s Luncheonette and a monster eating books, how all the kids turned into zombies. We had to save the town from getting rid of books. I had a great time. I wanted to try harder and get a bigger part.

CCB: In high school did you do more plays?

KG: It’s weird when your parents aren’t saying you can’t do something. In high school I was in the marching band, plays, and soccer. Got straight A’s. I got out of high school and I became an idiot. (Laughs) I went through a phase where I thought I was awesome in high school, thought I was dorky in college. Now I’m like (exhales) I was brave.

CCB: When did you realize you could make people laugh? 

KG: It was in Girl Scouts. Doing the skits around the campfire I would play the misfit, the idiot, the jester. I teach camp now and I see kids that are funny and they don’t know it yet. You put them in these roles and they kill. Overtime, I realized it comes naturally. Eventually if you want to do it professionally you have to train yourself.

CCB: Whom do you find funny? 

KG: Steve Martin because he shows jokes, doesn’t tell them. I am going into cliché, but its true they’re there because they inspire you as a young person. Gilda Radner was beautiful and funny, but you could tell she was a good person. Charming and funny, means more to me than being hilarious and an asshole.

CCB: You don’t want your idols to be jerks. 

KG: Who does? Adam Sandler and Will Ferrell are really silly and have a very particular sense of humor. Adam Sandler is so ambitious, cares for his friends. Will Ferrell is always 100% committed and hilarious.

CCB: Syracuse University is when you first try standup or pursuing… 

KG: Comedy. I was either going to study to be a Bio-Medical researcher or an actor. Two very different paths were in front of me. Maybe I should have gone into Bio-Medical research, but at the same time my philosophy is I can heal people with laughter. (Laughs)

CCB: Very Patch Adams.

KG: (Giggles) If I get into Syracuse and they give me enough money I would try to get into the theater department. Once you’re a theater major they make you feel very emotional. See the clown cry. I got sick of it and said I’m doing comedy. I don’t want to be a repertory actor. I respect their methods, but… 

CCB: Did Dave Malkoff, one of your college friend comedians, help peak your interest?

KG: In high school at the Thespian Festival I took improv. I had so much fun I brought it back and we did it during the intermission of plays. When college came around I knew I had to do improv and they had the Broken Compass Players at Syracuse. You can’t be in plays until you are a sophomore. Sophomore year they put me in the show. It was the coolest show, let’s have fun and improvise. Not I’ve got to breathe and emote. That was feeding the comedy bug. The transition to standup was through Dave who was practically head of standup. I was pretty much head of improv so we joined forces. 

CCB: Beginning doing standup how did you learn to write jokes and craft a set?

KG: I started to write a sketch about Titanic and Speed. What if Titanic was called Speed Control? The sketch never happened so I turned it into a standup bit and acted out all the characters. 

CCB: You didn’t seek out advice?

KG: No, I didn’t. I was working off plain instinct when I started. I got that there was such a thing as a setup, punch line to a joke. I never knew it could be mapped out as simple as that. That’s why it wasn’t stellar obviously. But, you could also have that formula and suck.  

CCB: What did you learn from your first appearance and as you progressed?

KG: I remember people laughed the whole way through and I wasn’t sure why. You hear so many stories about the first time people bombed big and I did fine. Two years ago I realized I could do the same material. I thought it was important to get a lot of stuff.  The importance of fine-tuning had to be nailed into my head. “I need to relax and perfect.” I’m not an act. I’m just a person constantly trying out new material.   

CCB: You started working on the play Long Day’s Journey Into Night literally right after graduating.

KG: The day of I was doing a press conference. So nerve-racking. Sam Waterston, John Slattery, and Elizabeth Franz were all seasoned actors. Worked so hard to do it right. Not only was I reading well I was making them laugh and that could not have gone better. It ran for about three months. By the end I was feeling lost because I thought somebody would have introduced me to somebody… I went in excited to be working. I came in with the right attitude, very professional. Learned my lines, learned my blocking. That aspect of the play I was perfect. In terms of having expectations I looked too far in the future.  

CCB: Were you learning different things from these seasoned actors? Any moment that stands out?

KG: In acting school you put up productions. The set was more beautiful. The costumes were more amazing. It was the money stuff. The simple process of acting and learning was not that much different. I think it was more in the philosophy of my career. You rise to the occasion. Probably the third week of the run Elizabeth Franz forgot her line. In a subtle way I reminded her what her next speech was, where she was going. She said afterwards, “you did it just like a pro.” 

CCB: After the play you show up in NY wanting to be a comedian?

KG: I thought I was going to be an actor and do comedy on the side because Dave’s (Malkoffs') brother had a sketch comedy show. After the play experience I was like I didn’t get anything out of that. Everybody exchanged phone numbers and I called once or twice, but chickened out asking for help because I didn’t feel it was my place. What are you doing? Let myself be in New York like as a college kid again. I went to open calls. People saw that on my resume, mentioned it. I went to equity open calls trying to get another paying gig. It was like banging your head against the wall because you realized they already cast things. I said fuck it. I’m going to do comedy because I am in control of it and nobody can tell me I can’t do it. I wanted to act. What young actor doesn’t just want to act?  

CCB: With comedy you can go to open mics. They can’t say no. 

KG: I started taking improv classes at the Upright Citizen Brigade Theater, doing standup. I was in charge of whom I was meeting. They were all at open mics, comedy clubs. These were my peers. At auditions everybody is all in their heads.  

CCB: Have you had anyone in NY mentor you along the way?

KG: Craig Baldo was my first comic friend. He took me under his wing introducing me to the discipline of being a comic because he was a really hard worker. You had to be out there busting your ass, writing your material, trying to make people laugh all the time. I went quickly from a traditional standup to guitar standup because I like music. Even though guitar comics are not well respected and it’s hard to make a living. 

CCB: As a female comic in a male dominated field, is that boy’s club just perception?

KG: At this point in society women are getting into leadership in offices and people will start accepting the female point of view. Right now it’s stereotyped into my period, shopping, I hate my husband. People respond because they want to see that stereotype. You have to look at the larger picture. One woman started talking about it and somebody laughed. How many male comics talk about their wives? Almost all of them do. It’s just a matter of being unique.  

CCB: Are female comics moving away from that?

KG: I couldn’t say that there is a whole revolution going on, but there are certainly lots of women with very silly senses of humor talking about different things. I grew up on the alternative comedy scene where everybody was cool, weird, and quirky. The alternative comedy scene is like the nerds. Whether you are a boy nerd or a girl nerd, it’s all the same. I didn’t go into clubs where it’s worse, a little harder to be a lady.  

CCB: You opened for Sara Silverman, how did that come about?

KG: I did the one-person show, Sugar Coated. Brian Billig saw my picture in Timeout NY so he came to see it. He had started booking comics on the road with a management company. Supposed to be Wanda Sykes and Wendy Liebman playing at Syracuse. Wanda Sykes bailed so he had to find some quick replacements. He said I’ve got Sara Silverman and 500 extra bucks let me see if Kimmy wants to do it. It was coincidence that I was free and he had seen me do a good job  

CCB: How did that go?

KG: It was good, really scary. 

CCB: What was scary about it?

KG: Going back to Syracuse not even a year since graduation. It was an amazing opportunity. That first gig you don’t want to screw up so bad. I sang three songs. The first two were lukewarm. The problem was the host was looking down at the paper. She welcomes me on. Everybody wants to see Sara Silverman and Wendy Liebman. I sang trendy girl from Shortround. (Shortround is a ska band she played in at Syracuse.) It killed. I had only seven minutes and I was out. Thank God. You’re so eager and want them to tell you, you did a good job. (Backstage) They were like, “you have a really great voice and that was funny.” I was waiting for them to tell me what to do. (Laughs) Cause I didn’t know what to do.  

CCB: What a great opportunity. Sara Silverman with her great name recognition as a respected comic.

KG: Sara Silverman always pushes the envelope. She wants a career, which means changing things up and doing interesting, different things. It was an awesome opportunity and you expect so much more. You just have to enjoy what you’re doing.  

CCB: Have you found female comics support each other being in the minority?

KG: I’ve definitely found a community. We did a standup show every Tuesday for about two years called Joystick. It was an all girls’ show. We’re all still friends, help each other, and work together.

CCB: You describe everyone as very supportive. What about that stereotype of unapproachable moody comedians? 

KG: Those people exist. I think it’s when people start getting paid to do it. You move up a notch you don’t want to take a step back. That is always an insecurity thing. When people pass someone in the comedy club they will still be pals but they are not going to come out and support every show. They want people supporting them. I feel like I am talking about psychology rather than comedy right now.

CCB: There is psychology involved. 

KG: There’s psychology because you are exposing your innards the closer you get when you are doing comedy. Finding something funny about themselves that they hate, stems from something deep that bothers them.

CCB: When did you get involved with Chicago City Limits, the improv troupe? 

KG: First year in NY was open mics, auditioning. Sketch, getting more involved with improv at UCB (Upright Citizen Brigade). The second year I did a Second City NY revue, was trying to get in Chicago City Limits. It took me four or five auditions and three callbacks. I finally got in and have been there for two years. I probably was talented enough for the show, but at the time there were a lot of people who wanted to get in so they could be very selective. Who has been around for a while, who has been taking classes from us. Recently we’ve been bringing in people who are really talented and they’ll come in and they’ll go. They want people who will be loyal.

CCB: Earlier you mentioned Sugar Coated. Can you tell me about that? 

KG: The beginning of my second year here I made a deal with my friend Brian Finkelstein. He said, “lets write a one-woman show.” It was that line between standup and sketch, but it was just one person. I did a lot of the producing. It was purging some ideas. Stretching myself where I’d never been stretched before. Some of it came out great and some wonky. It ran for eight weeks. I learned so much about myself. A focused idea usually comes out better. (Laughs) I had the energy, the emotion, and the talent. I didn’t have it written down was the problem.

CCB: Is that the most taxing you’ve felt performing? 

KG: I’d say so because you are on stage for half an hour by yourself trying to entertain the audience. I learned my strengths were living in the moment on stage, having lots of energy, owning the stage, being heard. My weaknesses are focusing the writing or trusting… If you are going to do a one-person show you should do it, fail, and throw it away. Everybody liked it. It was fun. I think that is a great word to describe myself, as fun. I wanted it to be something more meaningful than just fun.

CCB: As far as aspirations, what are your career goals as a comedian, actress?   

KG: I want to be a wacky next-door neighbor or a crazy secretary. Be a wacky next-door neighbor or a quirky character on an HBO show. In order to excel you sometimes have to give things up for a little while. I would love to have tons of experiences as an actress. I am trying to learn from my past experiences and focus. Not get so over ambitious that I forget what I am doing. Being a young woman in comedy is a great asset to have because there aren’t a lot of female comics.

CCB: You’ve done theater, improv, standup. Do you receive different things from each? 

KG: It varies things up as a performer. You do so much comedy you want to be taken seriously. If you are too much of a drama actor you want to be a comedy actor. Acting you feel part of the creative process in terms of making something and working with other people. You can’t concentrate on yourself when you are an improviser, but give to everybody else. Throw it up there and it’s never going to be repeated again. Susan Messing says its wonderful or its shit and its gone. Something is funny in the moment because you are making reference to an audience member who suggested it. There was a drip in the ceiling. Those elements in that moment crystallize it. If you transcribe improv I doubt anyone would find it that funny or moving.

CCB: Have there been moments of rejection trying to make it as a comic? 

KG: Sure, you start seeing people you’ve been working with succeed. You forget they’ve been doing it longer. You get down on yourself and your moral goes down, down, down. When you start comparing yourself to other people that’s a big trap that everybody falls into. Why am I not succeeding like that? Why am I not getting laughs like that?

CCB: How do you get out of that? 

KG: Keep going until you have a great show. You realize that there are so many things going on that don’t have anything to do with you. The best thing is you make people laugh again. It’s like a gambling addiction. (Laughs) When you win it feels so amazing and when you lose you have to keep trying to get that win.

CCB: Will you reach a point where you don’t want to do this anymore or will your drive keep you motivated? 

KG: I’m constantly re-evaluating my goals. Chicago City Limits can have its ups and downs since I’ve been there for two years, but I’m sticking with it. Suddenly I’m helping them produce a festival during the Republican National Convention. I’ve also been helping direct one-person shows for two years with Kirsten Ames. I’m starting to get paid to direct these one-person shows. One of them is going to The Fringe Festival. If you let things happen I’ve been finding them more rewarding. By learning more and more about yourself you learn more about your comedy. You are willing to be open and silly.

CCB: A lot of your material comes from real life. Enlighten me on your poem, Guy masturbating on a subway platform. 

KG: I was on the F train subway platform in Brooklyn and something caught my eye, like rapid motion. (Laughs) Nobody else was there because I just missed the train. Oh my god, I was freaking out. I didn’t know what to do. I started writing it down. For some reason…

CCB: You were writing the poem while it was happening?  

KG: Yes. (Laughs) It just got longer cause nobody else was on the platform. It was getting more and more awkward. The old joke is that I tell people that story and they say, “you saw me?” Ha, ha. It was probably my sixth month in New York. I don’t think I’ve ever seen a man masturbate before let alone in public.   

CCB: I don’t know where I go from here. 

KG: (In a creepy old guy voice) It doesn’t get any better than that.

CCB: Explain The New York Moves Magazine event you are hosting.  

KG: It’s a magazine for career women. They wanted a young up and coming comedian. I’ll welcome everybody. Probably do a twenty-minute set if I can hold their attention. Then just let people carry on.

CCB: What’s your involvement with Bootleg Islam

KG: Directing slash developing. Negin wrote most of her show that got accepted into The Fringe (A theater festival in New York City). It’s my job to say, this doesn’t make sense, where does the story go from here? Let go of your story because it needs to be fictionalized some. You exaggerate a bit like any good storytelling. We did the first preview show about a week ago. We got a lot of people’s feedback. It was good to see where the laughs are going to land, what people are grabbing on to.

CCB: Is it going to change a lot from the preview? 

KG: The normal process for anything is that it gets worse before it gets better. The preview point was probably its weakest point even though it was in really good shape. Having done that preview we re-wrote it and now it’s stellar. It’s crisp, clean, and we are going to open next Saturday.

CCB: It’s supposed to be funny? 

KG: Negin wanted it funny. She’s Iranian and wanted to show people the funny side of that. Try to get rid of some of the stereotypes she says like, “dirty little children running around.” She has funny stories about when she went for a wedding. She learned a lot about her culture since growing up in America she didn’t really know. 

CCB: Another upcoming project is Unconventional Humor with Chicago City Limits.  

KG: During the Republican National Convention there is a very liberal festival. It’s time to educate everyone about what is going on.  I’m producing a couple of shows of standup and hosting the Tuesday night sketch show.

CCB: The festival is supposed to educate people about the upcoming election? Not just going to be slamming Bush? 

KG: Arts and issues. Some people probably will. The intention of the festival is to bring politics to the surface.

CCB: Explain the pie section on  

KG: I wrote this play and at the end of every scene one particular character would get hit with a pie. Wherever he went it was like (Pie in the face noise). I make a really good chocolate peanut-butter pie and apple pie.

CCB: Have you found a place in NY where you can get a good slice? 

KG: The Little Pie Company is so good. It’s on 14th street. I also wrote Sound of Pie in the blackout, after the play. Started making up what the sound of a pie was in the desert, falling in love? It became very silly. If it ever gets finished people will understand what it’s all about. (Laughs)

CCB: Have any advice for people out there who have thought of doing comedy?

KG: Invest in yourself first as a human being and then you’ll have something to talk about that’s naturally going to be funny. I find the most comically rich moments I have on stage are from things that happened to me completely outside the comedy world. Network. Go see comedy shows and talk to comedians afterwards. Tell them what a great job they did. Learn from what they are doing, love it or hate it. Don’t give up. Keep trying.  

CCB: If you started doing comedy today, would you do things differently?

KG: I don’t think I would change anything. All these experiences are so great and stupid and lead me to this place. I don’t know if I’d be here if I change anything. I wouldn’t want to be uber-famous because I wouldn’t be ready for it I don’t think.

To find out more about Kimmy Gatewood visit