I stared at her Twitter page for like a hundred hours before deciding whether I should reach out to Jessi Klein. It seems like she's every writer's favorite writer, and I felt very undeserving of her time and energy (I'm writing this post from my laundry room). Jessi is currently head writer for Inside Amy Schumer with a very impressive past life working for Saturday Night Live and Kroll Show, among many others.
I guess it's no surprise she ended up agreeing to do the interview because hi, here we are, but I wanted to make it known that she's incredibly busy, is growing a baby in her body and probably has a lot of celebs to hang out with when she's not planning a nursery or writing perfect sketches like this one. Jessi, I'm thankful for your generosity (and probably sympathy), and I hope this project didn't put too much of a cramp in your sexy life.
I should mention there was some miscommunication about the selfie, so I decided to make it simple and just do what I do best -- draw a picture of her. It's basically spot on, so I'm sorry for leaving nothing to the imagination.
Jessi, I’m excited to get to know you better. You have a very warm and approachable presence on-stage, and I feel like it’s really going to translate here. I really fucking hope so.
The reason I reached out to you so eagerly a few weeks ago was because I witnessed an event on Twitter that I thought was really moving. Several of your peers started a campaign to nominate you for the next host of The Daily Show before they announced Trevor Noah. Did you feel as special as I felt for you? Haha I think the word “several” may be a slight exaggeration here. Mike Birbiglia, who is a delight, floated it out there and I think between forty and eighty people retweeted it. I can’t believe Comedy Central ignored this overwhelming outcry from the public. Still, it’s possible that was more people than Trevor Noah had.
I’m sure Trevor Noah is lovely as well, but when I saw the outpouring of acknowledgment I just immediately wanted to know your soul. My soul is incredible.
I knew it. You started your career working in development at Comedy Central, and it only makes sense that you found your way into standup while working there. Did you always want to pursue standup, or was it a product of being around it so much? I had always wanted to try standup but was too terrified. When I started working at Comedy Central, I saw enough good standup that it really inspired me, and enough bad standup that I thought, “well, maybe if I tried it I would at least be not THAT bad.”
Tell me about your worst standup experience. I was booked by a very nice Orthodox Jewish man to perform at what he said was a monthly “salon type” gathering at a gallery, and he was going to pay me, which was a big deal at the time because I never got paid to do standup then. Then the morning of the show he said there was a snafu and they’d lost their gallery space so were just going to do it at his and his wife’s apartment, but there’d still be “a lot of people.” I showed up and it was just him, his wife, and five neighbors. I walked in and said, “Um, I don’t think I can do this?” and he said it would be fine if I just talked about my life and answered their questions. It was completely bizarre. Did I mention I was getting maybe about two hundred dollars for this? Sadly, I’d probably still do it.
Season 3 of Inside Amy Schumer premiered its third season on April 21st. Tell me about the writing process. I’m really proud of what a genuinely collaborative process we’ve created for this show. Basically once a week or so the writers all come in and pitch. It’s always been important to me that the pitch process feels loose and open. Everyone’s encouraged to throw out ideas, even if they’re a little half baked, because even the thinnest half-idea from one person may spur an amazing idea in someone else. After everyone pitches, Amy, Dan Powell (the other executive producer) and I go through the ideas and decide what to have people write up for later in the week. Once we get first drafts, we give notes to the writer who does another pass. After that, if the sketch is working, the draft goes to the table for punch up, which tends to be pretty fun.
You’re head writer for the show. Describe yourself as a boss in three words or less. JK Simmons from Whiplash.
So inspiring. And so bald. What do you look for when you’re hiring a team of writers for a show like this? On a group level, we want people with different voices and diverse comedic points of view. It helps when you have a team of people who are all coming at the subject matter from a different perspective because it means everyone isn’t writing the same thing. On an individual basis, we want smart funny people who can write in Amy’s comedic voice and who are nice to be around. We’ve had a really great group every season. It’s fun to show up in the morning when you know you’re gonna see lovely people who may occasionally bring snacks.
My favorite moment from the show so far is when Amy and her boyfriend go to a couples’ counselor who turns out to be Chrissy Teigen. How did this concept develop? Ha, I wrote that sketch. I think Chrissy had maybe reached out to Amy that she was a fan of the show, or they were friendly on Twitter or something like that, so Amy wanted us to think about something for her. I’ve been to couples therapy and I just started thinking about what a nightmare it would be to be working on problems with your boyfriend with her in the room.
Is Chrissy Teigen funny in person? She is. She was great and totally game. What’s funny too is that she was really nervous at first, in a good way. You forget, when people are that beautiful, that they have insecurities too. I think for her working with Amy, she was nervous being in a room full of professional comedians - which makes total sense. But I was just staring at her waist and thinking it was the exact same circumference as the smallest part of my calf. I took a picture with her at the end of the shoot which was a really stupid thing to do. Don’t be in a picture with Chrissy Teigen. You will not look good in that picture.
She's a real life raven-haired Barbie doll angel if we're being honest about it. Tell me about your experience writing for Saturday Night Live. I grew up worshipping Saturday Night Live and it’s one of the main reasons I wanted to go into comedy . I was honored to be offered the job and I probably learned more there than I’ve learned from any other gig. That said, the process by which that show is made wasn’t really a fit for the way I enjoy working.
Some of the hosts you worked with include the massively talented Tina Fey, hilarious-and-knowing-he’s-hilarious, Alec Baldwin, and the lovable Betty White. How do you keep your composure around such icons? I tend to hide behind a tree.
Who is your favorite current cast member? I think there are so many insanely brilliant people on that show right now but I have a soft spot for Aidy Bryant and Vanessa Bayer.
When I die I'd like to come back as Aidy Bryant as Adele. Your sweet spot seems to be sketch comedy. Would you ever consider writing for a sitcom, or do you prefer the more segmented, short-form style of writing? It’s so funny that you ask that, because years ago I wouldn’t have said that my strength was writing sketch. In terms of my own viewing habits I’m a sucker for really quiet, quirky emotional comedies and dramedies. I just binge watched Togetherness on HBO which I thought was amazing, and then Transparent was one of my favorite things ever. I’ve seen Friday Night Lights, the entire series, twice. So I think of my instincts as leaning in the direction of that kind of material. It almost feels like an accident that I’ve ended up writing on so many sketch shows. I think my experience as a standup was helpful. But I’m proud that I’ve gotten better and better at it over the years. Part of the reason I love writing on Inside Amy Schumer so much is that the sketch we do is, by design, a little different in form than a lot of other TV sketch. We tend to write sketches that are paced more like dramatic scenes – it’s really important to Amy that everything we do is grounded in reality, so it feels more like you’re watching a slice of life.
You do so much in terms of performing and writing and being respected by everyone in the industry and basically just being a goddess of comedy. What would you like to accomplish that you haven’t already? If you could know how out of alignment this question is with my own sense of low self esteem your head would explode. As a baseline, I always feel so lucky just to be making a living by being creative all day and getting to work with funny people. If I allow myself to dream like someone who doesn’t have a boatload of insecurity – I guess I would love to create my own show one day. I’ve sold a bunch of pilots over the years but it’s such a mountain climb. I’m working on another one now.
You’re a self-proclaimed geek, but I have trouble with the term since it’s become so trendy lately. Prove to me that you’re a true nerd and not just being ironic about it. I’m not like a comic book sci-fi nerd. I just go deep into my own weird interests. I’ve read every Black Stallion book. I follow a lot of dog-based instagram feeds.
What do you want people to know about you that they don’t already? I’m really good at drawing animals. I can draw any animal. It’s a useless skill but at parties people are occasionally impressed.
It’s about to get real, Jessi. You spend so much of your time being funny, I wanted to end the interview with a series of though-provoking questions I’d like you to answer from your heart. Really dig in. Holy shit.
Who are you really? I’m someone who wishes I was Sofia Coppola.
What’s your biggest fear? I can’t choose one. My fears are like my children. They’re all my favorite.
Are you holding onto something you need to let go of? Literally everything.
When did you last push the boundaries of your comfort zone? Well I’m having a kid soon, so pretty much just that in it’s entirety?
Have you made someone smile today? I took a newborn care class today with three other couples and I think I pretty much killed.
Does it matter what others think of you? Oh fucking shit, yes.
What is your life calling? Doing this interview.
And breathe. Hopefully you feel liberated. I feel terrible.