When Roz Chast pops up on Zoom to chat, a fan of her work finds her exactly as expected: warm, whimsical, thoughtfully forthcoming, and wryly prone to place almost any answer into a broader framework of existential dread, with a colorful, obliquely zany sense of humor that makes you lean in and inspect carefully. 

Those qualities come through in Tired Town (Roaring Brook Press, Oct. 10), the new picture book—about a little girl who will not go to sleep—that she created with longtime collaborator, pal, and fellow New Yorker contributor Patricia Marx. These qualities also characterize Chast’s other endeavors, including a new adult book, I Must Be Dreaming, out later this month; the embroidery projects she shares on Instagram; the wacky ukulele duo she and Marx started as a lark, only to end up (surreally, Chast admits) playing with Isaac Mizrahi at New York’s swanky Café Carlyle; and, of course, the cartoons she’s contributed to the New Yorker for nearly five decades. 

Chast speaks to us from her Connecticut home. The Brooklyn native also keeps a studio in New York City—so small a friend calls it a “pomme de terre”—but she works primarily from Connecticut because, she says, the city is too full of exciting distractions. Our conversation has been edited for length and clarity.

How did you and Patty land on the idea for Tired Town?

Patty came up with it. We have overlapping senses of humor. I like the idea of a little kid who doesn’t want to go to sleep. Mykids never did. Now I have this granddaughter who’s almost 3, and getting her to sleep, there’s a whole routine. Little kids just don’t want to go to sleep. You pretty much have to tie them to the bed and say, “This is it. I brought you, like, 74 glasses of water. Mom and Dad haven’t slept in a year. Now you need to go to sleep.”

Do you relate more to the main character or the parents?

I can see it from both sides. That’s one thing about being a kid—you ultimately have to do what your parents tell you to. They’re paying the bills, for one thing. And you can’t, like, play dodgem cars with traffic. But some things, like going to bed, are hard to understand. This is what this little girl feels: “I’m awake. Why do I have to go to bed?”

Do you base your characters on real people, pets, or inanimate objects, or do they come from your imagination?

It’s almost always my imagination. But the building blocks of what’s in my imagination are probably real. I’m not drawing the exact lamps we have in the house, but they’re probably a mishmash of lamps I’ve owned or seen. I’m happy to draw interiors because my visual memory bank is interiors. I’m less good at drawing nature.

You and Patty were collaborators before you were friends, right?

Yes! When we were first starting out, in our mid 20s, in New York, she had written a humor piece for the Atlantic that I illustrated. When it was published, her mother said, “I like this illustration. You should call that girl; I think you could be friends.” Patty did call me. It was almost like her mother set us up on a playdate. Then we met a couple of years later at a book party. She was putting together a children’s book with Jane Martin, for Now Everybody Really Hates Me. They asked me to illustrate it. So that was the first book we collaborated on. 

Tell me about the collaborative process for this book.

With Patty, it’s different from other collaborations. She usually presents me with a vague idea, and I get a sense of whether this might be a project I could bring anything to. We do a lot of back and forth. Collaborating with Patty is less like, Here’s the piece. Now you draw the pictures. There’s a Venn diagram—she does do the words and I do the pictures, but she can give me suggestions or tell me to change something, and vice versa. Neither of us have a ton of ego in it. We just want it to be good.

You both started when there was this idea that women can’t be funny. Did you face headwinds?

Patty and I feel like we were lucky to be women starting out when we did. She was the first female writer on the Harvard Lampoon. I was certainly not the first female cartoonist at the New Yorker, but for decades there was this real gap. When I came in 1978, there was one other female cartoonist, Nurit Karlin, and she didn’t appear frequently. It was really, as they say, a sausage party. Patty and I have talked about that—in some ways, it was advantageous to us. I also felt that there were a constellation of issues when I came in: I was female. I was much younger than most people. My work didn’t look like anybody else’s. I felt like an oddball anyway, so I didn’t make too much of it. I should have probably thought more about it. 

Is there an element of this book you feel especially proud of?

I like the colors, the character.I had to redraw because when I first conceived of the character, I saw her as older. They said, “She looks too old.” I had to redraw her with a bigger head-to-body ratio. Redrawing is a pain, but you get to fix things you didn’t see the first time around. 

How did you come up with the color palette?

Color for me is just an instinct and some trial and error. I sometimes see a color in my head when I’m working, and I think, OK, that has to be this color. Then I futz around on the palette until I get that color.

How do you know when you’ve hit it?

It’s looking at it, and everything looks right—or as right as it’s going to get. Because there’s part of me that could—if I had endless time; if there was no such thing as death, not to put too fine a point on it, or sleep—take a drawing and rework it endlessly. 

Do you have any career goals yet to achieve?

Well, I would like to live inside an art supply store and set up a studio in there. Free art supplies for life. That would be good. Nah, I don’t think super far ahead because too far down the road is decrepitude and death, and that’s ever closer as I get older. I’m always just thinking a little bit ahead.

What are you working on now?

I’m still doing these embroideries; I’m kind of obsessed. And I’m starting to work on a collaborative graphic narrative book with a wonderful New Yorker cartoonist, Jason Katzenstein—he signs his work J.A.K. It’s about our sad kitchens. I like collaborations, but I’ve never done one like this. I’m excited about it.

Amy Reiter is a writer in Brooklyn.