'Inside Amy Schumer' Producer Jessi Klein Talks Chicago And Her New Book

By Gwendolyn Purdom in Arts & Entertainment on Jul 13, 2016 8:09PM

Jessi Klein knows funny. Aside from her gig as an executive producer and head writer for the Peabody Award-winning Inside Amy Schumer, the comedian has written for Saturday Night Live and Transparent and served as a regular panelist on the Chicago-based "Wait, Wait Don't Tell Me" podcast.

So, it makes sense that Klein would make a comedy-centric city like Chicago one of her first stops to promote her new book of essays, You'll Grow Out Of It, following its Tuesday release. Klein will sit down with Chicagoist's associate editor Gwendolyn Purdom to talk about the book at a lunch event at The Standard Club in The Loop on Thursday, but first, we caught up with Klein to get her thoughts on Inside Amy Schumer, our city, and, of course, how to be hilarious professionally.

Chicagoist: One of the things I think you do so well in the book—and, actually your team at Inside Amy Schumer does this so well, too—you take these seemingly insignificant or silly things and illuminate much bigger issues beneath them. Is that something you do consciously, are you looking for those little but actually big things? How do you choose those topics?

Jessi Klein: I think it’s a thing where all of these little specific struggles, they’re microcosms and with the stuff that feels headliney and political, the old chestnut is the personal is political. But I think it is. I just know the stuff that, as I go through my day, strikes me as feeling awkward and funny or a little off, and I keep a notebook and I try to remember them and write them down. It’s just the stuff that kind of suggests a story to me.

A lot of your essays in your book focus on womanhood. What would you say, off the top of your head, is your favorite thing about being a woman, and what would you say is the most obnoxious thing about being a woman?

That is a toughy. I feel like I would need years to answer that. My favorite thing, at least that I can think of in this moment, is I enjoy how much easier it is for women to connect with one another and make friends than it is for men. My husband is a very together and social guy but I just think women have a way of connecting with each other quickly and easily that I think is a real gift in terms of our ability to just communicate and connect. It seems like it would be kind of lonely to be some dude bro who can’t act like he likes another dude cause what if he’s gay, dude. Least favorite part? I don’t know. I guess my period?

“Inside Amy Schumer” is in its fourth, going-on fifth season. How would you say the comedy has evolved?

I think at the beginning we kind of found our footing. We just had no idea what we were going to do at the beginning, outside of Amy had such a strong comedic voice, we were finding our way in terms of the types of sketches we wanted to do. We knew that we wanted them to be personal but I think like most shows we kind of found our voice as we went along. And once we had a little bit of a sense of the idea that people were liking what we were doing, it gave us a little bit more of a green light to just own the silliness and the seriousness that we were embracing. And we worried less and less about “well, what will blah blah think?” Not that everything is perfect or everything hits but we just felt like we’re not going to worry too much about weather “guys” liked us. It’s honest and it’s true, so people will like it.

You’re a panelist for NPR’s “Wait, Wait Don’t Tell Me,” [which is recorded in Chicago], but do you have other Chicago connections? We’re something of a comedy town.

Sadly, other than just knowing a ton of Chicago comedy people who I adore, I have no connection to your people. I’ve always liked Chicago, I didn’t know that a city could be big and clean. I was just like, “How do they do that? Everyone’s just obeying? Putting things in the can?”

Before “Inside Amy Schumer,” you used to write for SNL and you’re surrounded by funny people all the time. What would you say is the quality that sets people who make it in comedy apart from people who don’t? What career advice do you have for Chicago’s aspiring comedians and comedy writers?

The first quality, and I guess this applies to everything, is perseverance. Persevering and sticking with it and a certain level of fearlessness, if we can define fearlessness not as the absence of fear but the ability to overcome fear. And then, I guess, being funny. And maybe some vulnerability. If you are somebody who wants to perform, just make sure you’re performing and if you’re somebody who wants to write, just make sure you’re writing. It’s so amazing to me, I’m a billion years old, I grew up without the interwebs, but everyone can be making something [now] without having to wait for someone’s green light and so that’s the main thing. I’m so intimately familiar with being paralyzed by the fear of starting and the fear of creating. And you think, well when will I be a writer? And it is kind of hackneyed advice but it’s when you start and keep going.

Doors for Thursday's event at The Standard Club open at 11:30 a.m.. For more information, visit Anderson's Bookshop's website.