Polymath Barry Phipps is a former art school kid turned musician whose skill set steadily expanded to encompass photography, modular synthesizer experiments, DJing, audio engineering and, most recently, forays into filmmaking. When he enrolled at the Kansas Art Institute to pursue visual art back in 1986, he was primed to seize every creative opportunity that came his way.
“Working with Archer Prewitt and the other guys in the Coctails,” he said of his former bandmates, “really stemmed from the idea that the Talking Heads met at RISD [Rhode Island School of Design]. That’s something I knew about in high school, and there was always this idea in the back of my mind, like, ‘When I go to art school, I’m going to meet some guys and form a band.’ I think we all felt that it was cooler to be artists who formed a band than to have studied music, so the foundation of what we did was influenced by the idea that the Talking Heads formed at an art school.”
Phipps was born in 1967 in Southern California, but came of age near Springfield, Missouri. At the end of his time at Kansas Art Institute, Phipps played in Mudhead, a noisy postpunk band that radiated Sonic Youth and Butthole Surfers vibes. Cartoonist and future Sea and the Cake guitarist Archer Prewitt was the drummer, and Phipps also played bass in a few jokey conceptual bands with Coctails members Mark Greenberg and John Upchurch.
“When the Coctails formed, I asked Archer if he would play drums for this loungey thing we were doing for an art opening, and he said, ‘Yeah, I’d love to do that, but I’ve also got some loungey things on guitar.’ Mark played drums, too, so Archer played drums on some stuff, and when he’d go to guitar, Mark would take over on drums.
The Coctails played their first show their junior year and performed around town for about a year, including a BFA show mounted by Giselle Simón, who is married to Phipps.
They originally called themselves the Coctail Twins — a play on the Cocteau Twins — then shortened it to the Coctails. The four began playing in clubs around Kansas City and recorded their first album, Hip Hip Hooray!, their senior year. After graduating in 1990, Upchurch moved back to his hometown of Chicago and the band followed him.
“Kansas City was not big enough for us to really do anything, and we didn’t want to go to New York or L.A., so Chicago seemed appropriate for us,” Phipps said. “When we were in Chicago, it was, ‘From Kansas City, the Coctails!’ And when we go back to Kansas City, it would be, ‘From Chicago, the Coctails!’”
While breaking into the Chicago music scene, they found their footing at the Lounge Ax and other prominent venues around town. The Coctails then hit the road, first on the East Coast and eventually throughout the rest of the country. On the first tour, they used the contacts they established in Chicago to secure gigs at key northeast clubs like the original Knitting Factory in downtown New York City and Maxwell’s in Hoboken, New Jersey.
“It was archaic, and it wasn’t that long ago,” he said. “Touring back then was kind of like getting lost for a couple weeks. It was trying to find the clubs using regular maps and all these handwritten directions. Everything was mom and pop, and every club had people that you associated with the club, and that’s how you made more connections. Every time we would play, next time we came back, there would be twice as many people. Because we had all these records and things to sell, people would buy them, and that was a big part of our distribution.”
By the mid-1990s, Phipps was looking back at his 20s and felt like he had done everything he set out to do in the indie music world. The Coctails became exactly the kind of band that they wanted to be: not famous, but they still left an imprint on the culture.
“We retired at the end of 1995,” he said. “We were all wanting to do different things, and we also didn’t want to be those people, like the age I am now, still up on stage playing the same songs that they’d written 40 years ago. We planned our last year and decided what we wanted to accomplish musically — putting out records and finishing projects — and then we ended by playing New Year’s Eve at Lounge Ax.”
Phipps’ second act revolved around being a jack-of-all-trades DJ. When the Coctails were winding down, he started spinning records at Smart Bar, a prominent Chicago club associated with the Metro. Phipps honed his skills playing to a packed dance floor every Wednesday night, and he eventually fashioned himself as a wedding DJ for those who did not like “wedding DJs” and all the corniness that term implies.
The Coctails temporarily reunited in the year 2000 to play the final night at the Lounge Ax before it closed for good. Four years later, they briefly got back together to open for the recently reunited Pixies during a two-night run at the Aragon Ballroom in conjunction with the release of the Coctails’ box set. In 2005, they also toured Japan to promote a new 10-inch vinyl EP that was released in that country.
Phipps had founded the Tight Ship Records label by then, and he also opened North Branch Recording Studio, where sessions for the Coctails’ final EP took place. Around the same time, he began recording his first solo album, The Town, a catchy collection of songs ornamented with gorgeous chamber pop arrangements. Completed in 2009, it was released as a vinyl LP in 2015 on Tight Ship.
“While running the studio,” he said, “I was working 10 hours a day listening to someone do 50 takes of a vocal. At a certain point I was just like, ‘Wait, I used to be a visual artist!’ I bought a crappy digital camera and I hated it, so as soon as I realized I could scan film negatives, I started shooting on film again. While I was running the studio and the DJ business, I began photographing at the studio and on breaks. Then I started offering wedding photography shot on film for people who didn’t want a ‘wedding photographer.’”
“When I moved to Iowa City, I suddenly had all these opportunities to be more of a photographer.”
In 2012, his wife Giselle Simón was hired as the Conservator at the University of Iowa Libraries. She is also an adjunct faculty member with the UI Center for the Book, having previously taught bookbinding and conservation at Columbia College. After 22 years in Chicago, Simón and Phipps were tired of the hustle.
“It kind of saved our lives in a way,” he said. “We would have imploded in Chicago, and when the recession and the housing crisis hit, it totally affected the wedding industry. All of a sudden, people would just plug their iPods in.”
One of the things that Phipps loved about moving to Iowa City after living in Chicago was that he could drive in any direction and within 15 minutes he’d be in a small town.
“That led to me doing a four-year study of small towns in Iowa — going out and photographing the same thing reiterated in different towns. All the towns have these same things, but it’s just a different iteration of it. So, my photography really took off, in terms of volume and growth.”
This led to his first book of photography published by the University of Iowa Press, Between Gravity and What Cheer, along with a second, Driving a Table Down. After Phipps earned an MFA at UI’s School of Art and Art History during the pandemic, he decided to dive back into music headfirst. The seeds had been planted in the 2010s, when Phipps began messing around with analog modular synthesizers. Simón loved what she heard.
“My first modular CD was called The Exuberance Phase, because when you’re learning a new thing and you don’t know what you’re doing, you end up making a kind of work that you’ll never make again. I knew that once I became more proficient, I would never be able to make sounds that way again.”
Over the past couple years, Phipps has been reinvesting in the infrastructure he needs to write and record music in his basement home studio. He is also learning to play drums, an instrument he had only dabbled with. At this point, he has entered his drumming exuberance phase.
“After going to art school, I was doing all music,” he said. “Then I was doing all visual art, and now I’m just wanting to reconnect with music and the idea of connecting with people again. Because the older you get, the less you’re doing things that can connect you with other people, and music can really do that.”
This article was originally published in Little Village’s November 2026 issue.
