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The Writers' Room with Jessi Klein

Every time you’ve laughed, Jessi Klein probably had something to do with it. With an oeuvre that includes Inside Amy Schumer, Dead to Me, Big Mouth, and more, Jessi’s comedic genius is undeniable — equal parts witty and biting, insightful and true. Her most recent book, I’ll Show Myself Out, is characteristically brilliant — an honest, hilarious investigation of motherhood unlike any we’ve read before, and a favorite of our founder’s. We had the pleasure of spending the day with Jessi at home in Los Angeles, where she shared the secrets behind her writing process, favorite writers’ room memories, and her wardrobe essentials, self-styled in pieces from our resort collection.


Photography by Emily Knecht

On Process

"I wish I could say I have a tried-and-true creative process but somehow it often still feels a little slapdash. I do have a few little key things. I think it’s good to start your day by moving in some way. A walk. A little trot somewhere. A crunch or two (but I mean don’t overdo it, part of the reason to be a writer is you don’t need to look that good.)

"When it comes to actually trying to write, I’m a believer in four hours a day as a good target — less than that maybe feels like you didn’t try quite hard enough, more than that and you might just start running out of gas. I believe in the power of getting up and walking away even if just for a few minutes. When I work on TV shows, I almost always have a new pitch come to mind on the trip back from the bathroom. If I feel really stuck I’ll confess a splash of wine here and there helps me."

On Wardrobe

"My favorite clothes these days are pretty, comfortable, and hopefully possess a bit of joie de vivre. The cable knit vest with the eyelet blouse is my dream combo: it’s giving serious writer but with a hint of romance novelist.

"I have never in my life been able to wear high heels — I think they look beautiful on people but I simply… cannot. Every time SJP would run in heels on Sex and The City I would just think… how? HOW?? Then I discovered Loeffler Randall heels and my head pretty much exploded. They’re so feminine and gorgeous AND have a block heel that is actually comfortable. Like ENJOYABLY comfortable. I want them all. I wore a pair to the premiere of I Love That For You and couldn’t believe I was at a fancy event and wasn’t suffering."

On Expression

"I love being in a writers’ room. It combines all my favorite things: laughing, being in a room full of funny smart people sharing juicy details about their lives, and snacking.

"When it comes to performing, there’s a joy in getting such immediate and kinetic feedback. I always loved the discovery and surprise of standup. Sometimes you think your joke is one thing, but then the audience laughs at some completely spontaneous tangent and you realize oooohhh that’s the funny part."

On Cultivating Collaboration

"Inside Amy Schumer was such an incredibly fun experience, and I think so much of it was that none of us — Amy, our other EP Dan Powell, or myself — had ever really been in charge of a TV show before. We (along with an amazing group of writers) just wrote what made us laugh and did it in a very collaborative way: no one felt pressure to have fully baked ideas to pitch, we would just share little scraps and tidbits of our lives and things that felt embarrassing or silly or awful. (I’m a big believer in tidbits — being comfortable just sharing a small piece of an idea that might spark the room.)"

On Writers' Room Memories

"In the first season of Inside Amy, one of our writers, the amazing Gabe Liedman, pitched a sketch early on called 'Compliments' in which a group of women are casually standing around and anytime someone is given a compliment, they instinctively reject it by saying something horrible about themselves. Everyone at the table recognized this self-deprecating behavior so vividly from their own lives. The day we worked on it as a group, all the jokes just flowed, it was like the most cathartic therapy. It was one of our first sketches to go viral, it still makes me so happy when I see it."

On Leaving New York

"Oh gosh, I miss everything about New York! I miss walking absolutely everywhere and I can’t believe I’m saying this but I even miss the subway. Just seeing so many faces and personalities and styles all the time. I miss Joe’s Pizza. I think maybe the only thing I don’t miss, and don’t tell them cause I don’t want them mad at me, but I don’t miss pigeons."