It was once safe to assume that if you were a fan of Paul Cherry, you were also from Chicago. But as the 70s-inspired pop prodigy continues his rapid ascent, that’s no longer a given.
Four months after dropping his debut album Flavour, Paul Cherry found himself opening day two of Pitchfork festival, warming the Green Stage for Moses Sumney and Fleet Foxes, among others. Cherry basked in the moment, casually tearing through decelerated arrangements off his serenely psychedelic pop debut.
As we sat down a couple hours after his set, the 26-year-old musician was on cloud nine. Stardom is still new for Cherry. He was taken aback when, after only a few sips into our beers, two fans ran up to introduce themselves and rave about his music. Only a few moments later, his smiling mother walked by, proudly clad in a Paul Cherry shirt.
Where is your favorite place to have a beer in Chicago?
Right now, it’s EZ Inn. It feels like a sick-ass basement and it has $1 Miller High Lifes on Sunday and Monday. If it’s too busy, I go to Stella's. I don’t like a busy bar.
What’s your go-to Chicago brewery?
I’d say Half Acre. I’m actually from Michigan, so my favorite breweries are Founders and Bell’s. I’m kind of an Oberon boy.
Who’s the coolest person you’ve shared a beer with?
Technically, sharing the beers is hard! But it was Clairo the other day. I got invited back to Clairo’s green room because she’s a fan of mine and it was really trippy. She didn’t drink a beer, though. I did.
If you could share a beer with one musician, who would it be?
Marcos Valle! He’s a Brazilian tropicana artist from the 70s and 80s. He’s still alive and has a funny Instagram. There’s a lot of Marcos Valle vibes in my music.
You were named after Paul McCartney?
Yeah, my mom named me after him, which is pretty crazy.
So, then, is Paul your favorite Beatle?
Absolutely, 100 percent. Paul is the trippiest Beatle.
Paul Cherry, though, is a “character”?
Kind of. It used to be. Kind of not anymore.
Getting away from that?
I think so. I think when I first started making music here in Chicago, I was doing a character thing and I was having a lot of fun with it. I was just able to do whatever I wanted, but I really didn’t know who I was. I kind of realized that I’m pretty much just chill. I write music that might make you feel like I’m a character, but I do think at this point, in the way that I’ve shifted my focus, I’m going for full earnesty. I think, especially in the time were living in, I would rather at this point just be very transparent. I have a fun, gimmicky name that works very well for me, but other than that I do like to keep it pretty real.
You’re originally from Michigan. When did you move to Chicago, and how did you get your start here in music?
I moved to Chicago in 2010 after high school and I graduated from Columbia [College] in 2014. Right after that was actually a weird time in my life where I needed to make money, so I made this Paul Cherry tape for funsies, and then I was also playing in this wedding band. That was my full-time job. It was a cover band. It was really fun at first, and then it was kind of soul-sucking when I realized I didn’t want to be playing other people’s songs, and at that point in my life I felt confident I could write good-enough songs on my own. That whole time in the cover band, the Paul Cherry tape was out. I was making music videos on the side for fun, but it was never that serious. Then, some of the songs got, like, hundreds of thousands of plays. I’m like, “Wait, did I make something that’s better than I think it was?” I was so sick and tired of the cover band that I set this long-term project in place where I would stay in the cover band and work Fridays and Saturdays. I would treat the work as play and the play as work. So, I inverted my mindset. I had a luxurious amount of free time. I dedicated all of that time to making a clean break from the band, making my own music and making it work. Honestly, it worked out pretty well.
I don’t need to be amazing at everything, but I need to be good at everything.”
At what age did you start playing music?
I got guitar lessons when I was 10. I was in orchestra in middle and high school on upright bass. I came to Chicago and went to college for electric bass and composition. I taught myself piano seriously after college. I basically got really serious and was like, “I don’t need to be amazing at everything, but I need to be good at everything.” So I decided I’m gonna do, like, five to six months on only piano, and then five to six months on only recording. It was a weirdly focused time in my life that I don’t feel like I have now.
You needed that to get where you are now, though.
It set me up, yeah. It’s pretty crazy putting all your eggs in one basket and it’s kind of paying off. It’s kind of fucking crazy. The response is way bigger than I could’ve expected. I did not expect people to like it as much as they did.
When you came to the first day of the festival, were you watching other artists and thinking, “Man, tomorrow that’s gonna be me”?
Yes, dude. I’ve been here almost every year. I think I’ve come, like, six out of the eight years that I’ve lived here. I’m always thinking, like, “That’ll never be me."
And then it was.
It’s so trippy.
What did it feel like standing up there?
First of all, amazed that the weather was so nice when I played. It had just been raining 20 minutes before. I was dreading all morning, thinking, “We’re gonna play to nobody. Everybody knows it’s gonna be raining and come later.” Then the clouds parted and everyone was there. I was looking out at the crowd and it was all my friends and a bunch of people I didn’t know singing along. It was maybe the most beautiful experience I’ve had in my life. It was so special. It felt like I was on drugs but I was completely sober. It was really bizarre that for so many years, looking at the Green Stage, thinking it would never be me, and then finally doing it.
Who are some Chicago artists that you’re into right now?
I would say Lala Lala for sure. Lillie is one of my best buddies and she lives on my floor in my apartment building. Her new song that just dropped is so freaking good. She’s one to watch.
Chicago has a very vibrant, loving and open music community. There’s a lot of diverse artists around here. Everyone seems to know everyone and they are all on the same wavelength. What makes Chicago’s music scene so different from any other cities?
Its very different than any other city, especially New York or L.A. You go to other smaller midwestern cities and there’s maybe one band who is blowing up—everyone gravitates around that band. It’s something weird about Chicago, where all these bands blow up and they all hang out with each other. And then they hang out with people that aren’t blowing up, and then it looks like those people eventually blow up too. It’s this mysterious, weird collective where everybody puts each other on.I have been learning that it is insanely special. It’s so weird to have bands that are doing so well just being there for you and ready to talk to you about the things you’re going through. It’s very awesome and not common.