Hold the jokes for a minute because I'm about to get real sensitive. This week I got to interview an incredible writer who currently works for one of my all-time favorite comedy heroes. Those who know me are well aware of the abiding love and respect I have for Conan O'Brien. I've loved him since the moment I laid eyes on him in sixth grade, and I love him even more now that he's lost a job at NBC, toured the country performing live for his most devoted fans and launched a new show on TBS where he's free to be the beautiful, untamed animal he is. Life threw him lemons, and damnit, he made the most delectable lemon meringue pie this side of the Mississippi.
Today, there is no one I would rather talk to than Jessie Gaskell, writer for Conan and all-around superb human. The fact that her work is present in the show every single day is something I could only ever dream of, and she does it so, so well. Not only does she write, produce, improvise (and, frankly, ball) she's also the regional director for a women’s writing conference that takes place in NYC and LA with fellow lady writers. You can check it out at bindercon.com.
Oh! And you can follow her on Twitter at @jessiestwats where you can expect thousands of professional selfies just like this one.
Jessica Gaskell, I want you to know I’ve never been more excited for an interview. Wow, seriously? Even more than your exclusive with JD Salinger? You’ve done interviews with a lot of people I admire, so that’s very flattering. Also, please call me Jessie, because that’s my name. Just “Jessie.” I know it’s crazy, but my parents were doing a lot of Tylenol PM at the time.
No, really. I’ve been staring at my computer screen for an hour just typing questions and deleting them. How can I do this interview justice? What can I ask you that helps emphasize how much I appreciate you? I think the name thing was enough. This has been great. Let’s call it a day before I have a chance to lower your expectations!
I don’t know how to say this without sounding hysterical, but Conan is my comedy hero. I grew up watching Late Night every night, and since I wasn’t allowed to be up past my bedtime, I would sneak to the basement and watch him on mute. His face brings me joy. Now that I’m saying this out loud, it sounds very disturbing. I feel the same way! I always felt very connected to his brand of humor, and he had a lot to do with my comedy evolution. It was basically Conan, Seinfeld, and SNL in my early days as a budding young comedienne (at this point, the reader tunes out, having been made suddenly and violently aware of my gender). Sidenote – is Conan better when you watch him on mute?
It's not completely the same not being able to hear his very masculine, baritone voice, but the string dance can exist on its own with zero audio assistance. Also, sometimes I slow clap for him when no one is looking. What? Let’s start from the beginning. You mentioned you grew up moving around Latin America. Explain this to me. Yep! My Dad worked for the State Department (cough, CIA) consulting on development projects (cough, military coups). No, he really did work with USAID, helping farmers in developing countries grow crops. We were part of this group of Embassy and military families who would get 2-year contracts and were never in one place for very long.
What was your childhood like? Weird! Interesting! Lonely! Looking back, of course, I wish I had been more appreciative of the experience I was having. I got to see how people lived outside of the U.S., and that did a lot to shape my world-view and perspective on how good we have it here. Also, I got to see a lot of beautiful and historic places, and I learned Spanish pretty much concurrently with English, which has been a huge benefit. So I appreciate it now, but at the time I complained a lot. Because I was isolated and couldn’t go ride my bike around the cul-de-sac, I spent a lot of time writing and watching TV. We had satellite TV so I was pretty much current with your average 6th grader who was watching Saved by the Bell and Fresh Prince for 6 hours every day after school while eating guava sandwiches. Everyone else did that too, right?
Ew, no. Guava? Gross. No, here in America we like to eat what we call "Extra Fatty Fat Fat Sandwiches". Speaking of your secret CIA family, there was a moment where you thought you would end up pursuing politics as a career path. What made you realize that was a terrible idea? Ha! I studied Poli Sci and Spanish in college, plus I interned with a senator and worked for various non-profits, when I wasn’t writing comedy sketches. But at the time I was all into you know, being the change I wanted to see in the world, and I didn’t think comedy was a viable option. After graduation I moved to D.C. to work for a think tank, and I was miserable - the only thing that made me happy was the improv group I was in. They all thought I was insane for moving to D.C. from L.A. to do improv.
Tell me about the first time you realized you were actually meant for comedy. Comedy was always a huge part of my life and the thing I loved most – it just took a while to click that I was “allowed” to do it as a career. As a kid I wrote these weird comedic short stories. In middle school I would make up Weird Al-style parody songs. In high school my friend and I cribbed SNL sketches and performed them at school assemblies - we’d do this Cheri Oteri and Will Ferrell morning show sketch “Morning Latte” but substitute in school news. And then in college I was part of a big sketch show and also hosted a comedy radio show. But it probably took going down the “legitimate” path and hating it for me to realize I was going to have serious regrets if I didn’t give my dream of being a comedy writer a fair shake.
Are you Type A or Type B? I don’t know! Which one do single men like better?
Type C: Anything that breathes. You started your career writing for a web series called “Dorm Life” which was a mockumentary about life in college. You co-created, wrote and starred in the series which is pretty impressive for a college graduate. Tell me about the experience. I did! It was my first real writers’ room. We worked about 30-40 hours a week together, creating a show bible, breaking out storylines, then writing scripts. We wrote and produced 40 episodes over 2 years. Oh, and we weren’t getting paid for any of it! What idiots. Looking back it’s remarkable that we were so committed to creating a professional show-running experience when we had no business doing so. But we took it really seriously, and we all made it work despite having day jobs. It was so rewarding to say we made it completely on our own without any “grown-ups.” And looking back, that may be the last time any of us get to work unconstrained by any network notes. At the end of it we were exhausted and wondered if it was even worth it, but I think it helped set us all on the right path.
You also worked as a writer on The Soup which led to a spin-off show called The Dish which you wrote for as well. Do you ever see yourself writing for a sitcom, or do you prefer a more short-form, segmented writing style? When I started I just wanted to do any kind of comedy writing I could, so I wrote everything - specs, pilots, screenplays, wafflemaker instructional manuals. At some point I started narrowing my focus to late night/variety, probably when I was working on The Soup and fell in love with fast, topical content. There’s something about the immediacy and high turnover that makes it exhilarating, and you never get too attached to your ideas, for better or for worse. But I’d be interested in transitioning to sitcom writing at some point. Having a strong joke-writing background is good, but you still have to learn how to tell a story, so that will be my challenge.
What brought you to Conan? Conan had always been my go-to, pie in the sky, dream writing job. Early on I was lucky enough to get connected with a Conan monologue writer, Berkley Johnson, and he gave me a lot of great advice about crafting jokes and late night writing in general. I won’t say he was my mentor because I’m not sure he’d want to be credited that way, but his help meant a lot to me. Then a few years ago I was hired to write on a Conaco-produced sketch/talk show hosted by Conan writer Deon Cole. It was called Black Box, and unfortunately only lasted for 10 episodes. But through that, I was introduced to more people at Conan, so when they were hiring later that year I submitted. I think it helped a lot that they already had a reference to my work and knew I wasn’t going to steal office supplies.
Talk to me about a day in the life. What is it like going to work every day? It’s incredibly fun - as long as I can remember that we’re producing comedy, not performing emergency surgery. It’s funny how quickly you lose perspective and find yourself super stressed because you needed a blow-up doll for a sketch, but the one the props department bought has a weird face, which isn’t the joke, because it’s just supposed to be a straight blow-up doll, so now you’re painting a new face on the weird-faced blow-up doll. Or you’re in with the graphics department and someone is literally speed-drawing a picture of a penis for a news parody that’s going on the air in half an hour. And then you’re debating, “Should the balls have hair? Is that a nice touch, or does it make it TOO realistic?” I work with the funniest people on the planet in an exciting and challenging environment, which is exactly where I want to be.
What is the writing process like? We come in every morning around 9, have a pitch meeting at 10, then if one of your pitches gets accepted you’re off and running. If it’s something for that day, it’s a crazy-fast turnaround: you have to have it done by rehearsal at 1pm. Or you might have a video piece that you’re rushing in to Conan’s dressing room right before the show, which is an intense amount of pressure. Usually everyone’s concurrently working on a longer-term project that might be for later that week. And we do a combination of solo writing and collaborating, depending on what needs to get done. Because the time frame is so tight, there’s almost always something you wish you could have done better or taken more time with. But the upshot is it’s done and you don’t have too much time to dwell before you’re back at it again the next day.
Oh – one thing I should mention because I think a lot of people don’t know this, but we produce all our own sketches too. So everything from casting, to sound effects, costumes, graphics, we cover all of that. We have extremely talented people in all those departments who we work with, but it’s totally your responsibility to see something through to the end. It’s not like you print out a page and hand it to someone and then go to lunch.
That makes perfect sense, so the concept doesn't get lost in layers of communication and ownership. Very wise. Conan seems to care a great deal about what he does, who works for him and keeping his fans happy. How involved is he in the day to day writing process? Conan is the smartest, funniest person in any room he’s in, so the meetings where we get to hang out and brainstorm with him are incredibly fun (if not productive). I spend most of the time laughing so hard I’m crying, and then regretting that I didn’t wear waterproof mascara. Conan’s super involved in that he approves all the pitches, then when we rehearse something he’s always improvising and tweaking things, and his input always makes it funnier. He was a writer first, so he’s really hands-on when there’s an idea he thinks has potential.
What’s your favorite part about working for the show? I love the immediacy and variety of what we do. I love the rush of producing a sketch and getting it on the air. I love when someone has a birthday and there’s leftover cake in the breakroom.
Do you know how lucky you are? Oh, yes!
There is nothing funnier on planet earth than Conan doing a remote. He most recently crashed a viewing of Magic Mike XXL. How much writing and planning goes into a segment like this? I agree! I’ve produced a lot of remotes, including the Magic Mike remote. I love the remotes because people get to see how quick Conan is on his feet. He also has this great improvising style where other people get to be the straight man and he’s the butt of the joke, which means everyone’s having fun and no one feels manipulated. The metaphor we often use when producing is that we’re creating a jungle gym, and then letting Conan play on it. So a lot of it involves coming up with premises, locations, characters, and props that you know he’s going to have fun with. Then you make sure all of that stuff is ready to go (like immediately ready to go, there’s no down time) and Conan comes in and we just shoot everything continuously. Sometimes there are lines I throw out there but most of it is Conan improvising. And then I take all this footage into the editing bay, and we output the funniest possible version.
The show has a massive digital following with TeamCoco.com acting as the hub for fans to engage and interact with all sorts of content from the show. Do you write any exclusive, online-only content? Not…usually. Sometimes we have things we create that end up online because they’re not quite right for a live audience. But there are also weird WGA rules that govern the web and we’re not allowed to go over a certain time limit or else they have to pay us more. I don’t totally understand it. There’s also a whole separate wing of web content creators that work for TeamCoco.com, and they’re putting stuff on the site daily.
How do you feel about the world of social media? Exhausted? I think it’s great that there are so many outlets for comedy and that more people have the opportunity to create content that gets seen by a lot of eyeballs. It makes the whole system much more democratic. And it’s interesting that TV shows are now competing with people who are making memes and photoshops and video re-cuts. I’m constantly amazed at how fast that stuff gets made and put online. But also, no one knows exactly how to make money doing it. I think most people are doing that to eventually get TV jobs, but TV is being replaced by these other mediums. So it’s a bit of a Catch-22. For me personally, I like having a place to workshop ideas and put things I couldn’t put on the show. But the flip side is I feel a lot of pressure to have this cohesive online “brand” and be marketing myself. Some people are really good at it, and I’m very jealous of them. I don’t know how to take selfies (see above). I want there to be a class that teaches you how to take selfies.
It's only a matter of time before professors are teaching How To Instagram a Salad 101. Most of Conan’s fans are like me and have been fans of his from the beginning. How do you keep the show fresh while still nurturing its essence? I think late night in general has entered new territory, because most people aren’t actually recording and watching full episodes, but they’re watching clips online. In this sense it’s smart when we can do stuff that stands alone and is also internet friendly. But a lot of people really enjoyed Late Night (as in, Late Night with Conan O’Brien) for its weird absurd character bits and anti-comedy, and we’re all still big fans of that too. I think the remotes are a nice blend of Conan being Conan, and having something that plays well online as a stand-alone video.
What can Conan fans can look forward to in the coming weeks/months? We just got done shooting a week of shows at Comic-Con, which went fantastically well and I think everyone’s feeling really energized right now. It was such a natural partnership, I can’t believe we hadn’t done it before. I think there’s a lot of crossover between Comic-Con fans and people who enjoy the type of comedy we do at Conan. At the end of the week, we announced we’re going back to do the same thing next year, so I think that’s going to be an ongoing fixture. And shooting our special in Cuba got us excited about the possibility of doing some more adventurous travel shows, so we have some locations in the works as well. North Korea, perhaps?? “Conan digs a mass grave for dissidents!”
You have experience in all aspects of comedy, from producing to writing to improv. What gives you the most gratification? I’m so glad I have experience with all of them, because they feed each other. To use corporate speak, they’re very synergistic. I’ll circle back to that later when I come up for air. I love writing, but the best is when I get to produce the thing I’ve written and have the ability to bring my vision to life. And I love performing in stuff I’ve written when it’s in my wheelhouse. But like, I’m probably not going to do a good Margaret Thatcher impression.
What’s next for you? The comedy writing thing’s fun, but my real dream is to open up a bakery! You know the middle part of the cinnamon roll? We would just sell that. It’d be called “Cinnamiddles,” something like that. No joke – I am constantly coming up with ideas for “fake” businesses that I half-start, buy the domain names for, then give up. I wish someone would pay me to do that.
Here's a freebie: "Cumberbuns" -- a sandwich wrapped in cucumbers instead of bread. It's healthy, so I feel like the state of California would eat it right up. Anyway, I feel bad you’ve missed out on your political career, so I’d love to end the interview with a very bureaucratic writing exercise. You are running for President in 2016. Write your formal campaign announcement. “Hello, my fellow Americans. I have only one campaign platform. Only one promise to you. Vote for me, and I will pass a law that McDonald’s has to serve breakfast all day. That is all.” *Drops mic* *Wins 100% of the popular vote.*