There’s a lot that makes going to shows magical besides the live music, and no one knows this better than Empty Bottle art director Bill Connors. The Illinois native never expected to be guiding the aesthetic of one of Chicago’s most beloved independent venues, but the job has proved a natural fit: Since high school, Connors has experimented with music and video projects, playing with how moments of sound and image can be combined to create new meaning. At his core, he’s always been a visual thinker, capturing the attitude or essence of an artist or event with a collage-style approach to gig posters, album covers, logos, and T-shirts. Connors is formally trained as an artist, but he prioritizes cultural ephemera—which he sees as accessible art objects—over collector-driven fine art. His signature style—something like art nouveau skateboarding in a garbage can—has appealed to acts as divergent as Post Malone and Metallica. His career hasn’t been easy or straightforward, but his work is already proving influential.

As told to Micco Caporale

I grew up in Orland Park and started attending SAIC in 2007 and graduated in 2012. In 2010, I started couch surfing until I could live in the city full-time. I really found a home in the printmaking department, and I took a lot of studio classes so I could stay in the buildings overnight and crash on a couch when I got tired.

I’m a huge fan of the Chicago Imagists—like the Hairy Who kind of stuff. A lot of that was painting, but their book stuff got me into the world of offset lithography, which led me to screen printing. That got me thinking about translating these higher-art paintings into something ephemeral, like a zine or pamphlet. Something not very precious. And from there I got interested in show posters. I can remember being at Handlebar for the first time—in, what, 2008?—and seeing Ryan Duggan’s work. He’s got a very particular hand-illustrated style with this really sharp sense of humor. Always an inspiration.

SAIC is a very conceptual school, but I’ve never felt like I had a place in the conceptual-art world. I like making for making’s sake. I always felt out of the loop with that “precious art” thing. I don’t come from a place where anyone I know owns or wants to own a bunch of expensive paintings. What I do want are things that I collected over my life that mark time, you know? And making that accessible to more than just, like, people I met in school.

My art is so eclectic. I know everybody says that, but the kind of art that I like and the kind of music that I like—I don’t know if they necessarily overlap. Like, not in a way where I’m like, “Oh, yeah, I definitely see the connection between this music and this artwork!” That’s not always my favorite moment. I really, really like when things go off-kilter.

When I was in high school, I’d share stuff online. In the LiveJournal/Blogspot days, people would chronicle every moment of their life in great detail rather than, like, a quick snapshot, so it felt like a great place to share work and get feedback from random people in a way that was natural and helpful for me. It was a great environment to get a discussion going about some drawing that I was working on with my friends who were just trying to, like, skateboard. 

I wasn’t trying to advertise, but here’s where that becomes sort of a thing. Because by the time I was 21, I was negotiating with bands and companies that were, like, in Australia. I did something for Converse right out of college because I was sharing so much work online. I’m very grateful for everything that’s come my way, but at the same time, it makes me afraid.

The algorithm has got me pegged to a degree. It’s feeding me the same kind of images and artists who are doing work in a specific way. Sometimes it ends up distracting me from what I’m working on, like having too many reference points for your own work. But it scares me too, because I’ve gotten offers from companies or whoever where they’re very excited but want to charge a very low rate. And then you counter and immediately feel that gust flow the other direction, like, “Oh well, if this guy won’t do it for 40 bucks, I’ve got 100 people on this app who will!” 

I see it a lot with companies that I know have the money, but they bank on you wanting their endorsement or to feel part of their “team” or whatever. But it’s like, I need to pay my rent. I need to pay for food. I need time to do human-being things. It’s a constant turn and burn. I don’t know how people rely solely on freelancing. Nothing but respect from me.

In 2014, I started working the door at the Empty Bottle. Most people didn’t know that I had this art career outside of work. But once I started doing more work for bands that were touring and coming through the Bottle, people started connecting me to the place, and I started getting more offers. Eventually I started doing graphic design here and there for the Bottle, and then I graduated to my current role as art director. That’s a new role, and it happened during the pandemic so we could focus more on merch and branding. 

Bill Connors created these artworks for the Empty Bottle and for Los Angeles band Cobra Man. Credit: Bill Connors

Every time we have a show—all that stuff on Instagram—it’s hand collage, which is a little bit more than I should have undertaken, but I like the way it looks, so. . . . 

I’ve always been into collage, like rooting through magazines and collecting images to use in different ways. I experimented with digital-collage stuff in high school—just poking around Photoshop and Illustrator for years. Those were rough. I learned a lot of different collage techniques in school, but those were mostly physical collages. In school, I was really into physical materials and scanners and physically printing things and then scanning the things that I physically printed. And it got into this whole process of physical, digital, physical, digital, just back and forth, you know? Which also lends itself to Xerox stuff, right? Like, the more times you photocopy something, the more blown-out it gets, and you can create these little worlds, especially adding hand drawing. 

People always ask me, like, “Oh, are you really into, like, punk artwork?” I like that kind of thing, but it’s always been kind of an afterthought to me. I just like that photocopy look in general. It feels timeless. It’ll always look like the perfect age because it can be any time.

I don’t really have a process. There are steps, sure, especially with the scanner, but I’m like the trashman. I use everything and anything. I work digital and analog. I’ll scan things, use other people’s scans, take photos, find photos, add drawn elements by hand or in the computer. What I’m most interested in is a collage that feels like a collage but doesn’t necessarily look like one, you know?

Right now I’m trying to make work for posterity. I’m not interested in “clout.” I’ve worked with some big people, but I don’t always post it if I’m not into it. I wish I had more time to regroup and just make something for me instead of clients. I don’t want to be depressing, but I don’t want to lie to people either. Sometimes I think it looks like I’m killing it, but I’m not. I’m really not. I’m so broke and tired. 

That’s the thing that kills me about the Internet. People think, like, “Oh, this image will get me a bunch of followers, and then with a bunch of followers, we’ll get a bunch of money.” But exposure and followers don’t translate to money.