Chicago's Rising Star: Kara Jackson at Pitchfork

When I ask about her time in the Laureateship, she's somewhat coy, describing it as her “past.” Fair, but Jackson’s years spent honing her skills as a poet have so clearly shown up in her music. There’s not a syllable out of place on her 13-song debut, which is at once irreverent and profound, a moving journey through grief, love and the regular rhythms of becoming.

Having grown up attending Pitchfork Music Festival, Jackson is set to perform there this Saturday. When speaking about taking that stage, Jackson moves between a sense of joyful shock that she's set to perform and a rooted sense of predestination. Pitchfork has long featured local Chicago acts. She has friends and collaborators who have played too and she grew up seeing the artistic generation above her perform there as well. It’s an honor, but not the wildest leap that it’s finally her turn. Regardless, she’s sure to make the most of it.

Jackson chatted with PAPER a week before she’s set to play her hometown’s coolest festival to talk about Chicago’s poetry scene, early success and touring her very personal debut album.

You're from Chicago and playing Pitchfork. I’m curious if you went when you were younger?

Yeah, I would go as a teen. I started going to Pitchfork when I was like 15 or 16. I remember my best friend and I really wanted to see Chance the Rapper and I started going every summer since then.

From your perspective, how does Pitchfork fit into the Chicago music ecosystem?

I think it's its own particular thing, because it's not the same beast as Lollapalooza. You could see someone like Dua Lipa at Lolla. At Pitchfork, historically, there's been more of an emphasis on indie artists, the kind of artists you'd see reading Pitchfork. Local acts have also always been such a thing. So I've grown up seeing people I really admire play Pitchfork, like Jamila Woods and my friend who helped me on my album, Kaina Castillo and Sen Morimoto. I remember rushing to get to Sen’s set like last year. It's really cool to see how the local music scene influences Pitchfork’s lineup.

How does it feel playing Pitchfork, having been there growing up?

I think it's definitely trippy. I've always wanted to play Pitchfork. Having seen my friends take the stage, it's always been a big dream of mine, so a part of me has been counting down the years. It's crazy that it's happening because it feels like one of those things that you don't really know if it's gonna happen. I'm still mentally getting ready. I still think I'm going to the festival to attend and see people. I'm like, “Oh, okay, Carly Rae Jepsen's playing.” But it's weird that it's my gig. I have to show up for my own set.

I know from friends who grew up in Chicago that the youth writing community was a central experience for a lot of young creatives in Chicago. And many musicians like Noname and Saba were a part of that as well. I’ve seen you talk about that time a bit, but I’m curious how it shaped your artistry?

I definitely grew up seeing Chance the Rapper at open mics. Saba talks about going to open mics in his songs. That was such a defining aspect of my teenagehood, and it gave me some of my first opportunities ever to share my work with people my age. I remember the first time I got to sing at Chance the Rapper’s open mic. It still is like such a big deal for me getting to interact with [Chicago artists] as an adult because I feel like I grew up being obsessed with Noname, Jean Deaux and Ravyn Lennae, just seeing all of them occupy this space and take control of these stages. Young Chicago Authors gave me my first artistic job. I worked there as a teenager doing poetry and going to poetry workshops. But it also gave me my first artistic community and let me have friends who also made art and wrote things.

I think that space really gave me a concept of what it actually looks like to be a working artist. It allowed me to understand that my dream is something tangible, because I think it takes looking at someone like Chance taking off. That was such a big deal for me as a kid, seeing him get really famous, or seeing Noname drop her first projects. Those were celebrities to me, but seeing them become celebrities to the world was such a crazy thing. So I think that those spaces growing up were common denominators in all of our stories.

Did poetry and music always feel connected to you?

Chicago is an interesting location for both music and poetry. There's such a unique history around poetry especially, because the Poetry Foundation is here and Slam Poetry was born in Chicago at the Green Mill, this place on the North side. There's this really particular overlap between the two artforms. I grew up going to poetry workshops, but also there would always be a poetry workshop followed by a rap workshop right after. So there's a really natural ebb and flow between the two to me.

I'm sensitive about people saying, “Your songs are poetry.” I understand my songs as songs, but I definitely can see how poetry, and doing poetry as a discipline has influenced the way that I approach making music and the way that I write. It was just so normal to see someone get up on stage and do a poem, and then the person right after them does a whole song. A lot of people I know who are rappers were poets first. It’s an interesting phenomenon, the way that those disciplines inform each other here.

You were the Youth Poet Laureate of Chicago and then the National Youth Poet Laureate. What did that entail?

The Youth Poet Laureateship of Chicago was really cool because I was responsible for making a little book of poetry. And through being the Youth Poet Laureate of Chicago, I applied to be the national youth Poet Laureate because each person who applies represents a certain region. A bunch of people apply and I was the Midwest representative. I think it was really the first time that I had an official role with poetry. The Youth Poet Laureateship is essentially representing your country as a poet. I wasn't writing patriotic poems, but I was given this title, and it's a big honor, and you have to go to the Library of Congress.

I can only imagine how having that success as a very young person shapes you. What was that like?

Everyone has this in their own respective fields and areas, but especially in creative things, whether you're writing for a publication or doing music. I think that everything is a mixture of luck, and then that forces you to discredit the actual work you put into things. I think that imposter syndrome is a weird thing 'cause I don't think that it's a thing that I like to give a lot of fuel, but I do think that it comes up especially as a woman of color, always wondering like, “Oh, do I deserve this?” For me, I'm really bad at processing things in the moment. It takes me years to process the magnitude of things sometimes. Like with the National Youth Poet Laureateship, I think I got ... not embarrassed, but I was just like, “Okay, that's like my past. I was like 19.” And it was such a specific thing.

But with music, I've always wanted to do music, and I've always wanted to share my music with the world. And so I think that has been really unprecedented, seeing the response [to my music] or getting to play something like Pitchfork. I think I'm not always present for those moments. It'll be a week later, and I'm in my room playing Animal Crossing and I'm like, “That's so crazy that a week ago we were playing this festival.” It takes me a second sometimes because, to me, I’m really normal, and it's just weird that these songs that I wrote about my own life are alluring to people. But it’s humbling and freaky at the same time.

You just started touring for the first time?

Yeah, I just did a bunch of headlining shows in the US and Europe and May through now. I just got back from Europe about a week ago.

What was it like to play these very personal songs for audiences? I'm sure people have personal connections to them.

Touring the songs gives them such a different life and interpretation. It's interesting energetically to see a crowd reacting to them, or just offering them up in that space. I think making the album is its own energy, being in the room with people you trust. But taking those songs out in the world is so interesting and seeing what resonates. I think it's always a surprise. Also, in each city it's different, so it's cool to see different crowds. Sometimes it's weird to perform in front of different crowds, because different cultures have such a different way of engaging with live music. Sometimes people would be dead silent, and I would be like, “Okay, I hope everyone is enjoying this!” [Laughs] It's definitely been cool and I'm glad to be back home and resting up before Pitchfork.

I’m curious about any other Chicago artists that inspire you? What's exciting you?

There's so many people in the Chicago music scene that inspire me. especially my collaborators, San, Kaina and Namdi. But I have been so lucky to be taught so many things by Jamila Woods, and even the real OGs in Chicago like Krista Franklin and Avery R. Young are people who always really inspire me. People like Jean Deaux, Noname and Ravyn Lenae, those women gave me so much of a sense of confidence, just by watching them and aspiring to what they were doing. [Having] examples of Black women doing music and being creative and being themselves really gave me the tools to do the same thing, so I would definitely shout them out.

Photography: Lawrence Agyei, Ash Dye