Olivia Lilley Credit: Jeffrey Bivens

It all began in 2015, when Olivia Lilley made a deal with the devil.

At the time, she was new to the Chicago theater scene and out to produce a living-room tour of Faust with her experimental company The Runaways. That was when Prop Thtr cofounder Stefan Brün got in touch.

“I was crowdsourcing apartments on Facebook when Stefan found me,” recalls Lilley. “He was like, ‘You’re doing Faust? Let’s get coffee. I want to talk.’ We went to this little restaurant in the Gold Coast called 3rd Coast, a very old-school diner within a bourgie neighborhood, and we had a three-hour conversation.”

Brün believed she would fail. But “failure” is a murky term in the ever-defiant and cash-strapped world of experimental theater. Brün wasn’t talking Lilley out of the production; she sensed that he was throwing down a gauntlet.

So she persisted.

“I said, ‘Oh, yeah? Watch me. Does the Prop have any spaces?'”

Doubling down on his dare, Brün let her use the apartment above his theater for the final tour stop.

“I was a bit nervous because I had to impress this guy,” she says. “But he left that night and was like, ‘All right, bitch can play.'”

Or, as Brün puts it, “Boy, I was wrong.”

In fact, Lilley could play the avant-garde game so well that three years later Brün offered her the position of artistic director at Prop. She and I met there one night to talk shop.

The theater’s lobby is every bit the “La Vie Boheme” fantasy that most drama kids envision after they watch Rent for the first time: mismatched furniture, piles of costumes, worn posters, moody lighting, chalkboards covered in a variety of handwriting, irreverent relics from shows past, and a constant draft so that we had to wear our winter coats to keep warm.

Lilley’s calm and articulate demeanor feels like a foil to the mayhem, but the building’s funhouse vibe speaks to Prop’s history. After producing student theater at Columbia College, Brün and Scott Vehill introduced Prop in 1981, in a former strip club on Lincoln Avenue in North Center, right next to the old Clear- water Saloon. The duo set out to create the home of Chicago experimental theater. Together, they began producing work driven by the current cultural climate instead of adhering to a rigid institutional mission; it was about nourishing new voices and getting weird and reacting to the now. Nobody was out to sell their souls.

“Stefan and Scott would go back and forth between acting and directing,” says Lilley. For Prop’s first official show, Brün adapted and directed Bertolt Brecht’s Mr. Puntila and His Man Matti; Vehill starred.

Vehill and Brün eventually found Prop a new home in Lakeview, and began renting out the hallways to the people they made shows with. It was a neo-beatnik utopia, Shakespeare with liberty spikes.

“Five or six years into it, the lady punks began doing their stuff in the space,” Lilley continues. “I wish I was there to see it, but it sounded very sexual and incisive and ritualistic.”

In 1994, however, Prop put on an adaptation by Paul Peditto of Nelson Algren’s Never Come Morning, directed by Jennifer Markowitz, which wound up taking home nine non-Equity Jeff Awards, including Best Production. According to a Jeff rep, it’s still the record to beat.

The “grown-up phase,” as Lilley calls it, continued. At the end of the decade, Prop helped found the National New Play Network, an alliance of more than 100 theaters across the country (including six others in Chicago) that support and collaborate on new dramatic projects.

In 2005 Prop moved to the two adjoining storefronts on Elston in Avondale where it has lived ever since.

Lilley seems to be a perfect fit for Prop’s highly stylized yet unruly ethos. She originally set out to be a music composer as a teen. She wrote a feminist version of The Phantom of the Opera when she was 13 and attended the Interlochen Arts Academy in Michigan. She fit in with “the baby queers” who were into futurism, while her male music classmates called her “three-chord Broadway.” In college at Carnegie Mellon, Lilley studied music composition but did everything she could to avoid writing music. After three months, she transferred to the directing program. She spent her time off from school interning at theaters in New York, including the late Incubator Arts Project, which housed playwright Richard Foreman’s Ontological-Hysteric Theater.

“It was a company that did a lot of artist-led works, so seasons at Incubator usually revolved around lead artists’ crazy projects,” she explains. “It wasn’t like, ‘This is the play, this is the cast, this is what we’re doing.’ Those people were in conjunction with [experimental playwright] Young Jean Lee and her teachers—folks like Jeffrey Jones, and Mac Wellman, who’s sort of the godfather of downtown theater.”

In the tempest of these dramatic forces, Lilley began to hone her own approach to theater and after graduation took off for Chicago.

“I didn’t feel like I found my people in New York City, and I also thought I would be the worst assistant,” she says. “I also really wanted the opportunity to actually direct and create shows from start to finish. NYC was way too expensive. When I opened my first show in Chicago, it sold out, and I didn’t know anybody who was there. That kind of thing would never happen in NYC. I remember thinking, ‘Chicagoans just like going to theater. Wow.'”

She also decided not to play “the game” when she arrived.

“You know, you assistant direct for someone and then they recommend you to someone else, and then they recommend you to someone else,” Lilley says. “I was too much of a fucking punk. I wanted to figure it out on my own.”

Lilley is the type of artist who will rent out an entire house in Pilsen so she can produce a show about a year in her life.

“I called it The Party House,” she remembers. “The characters were all based on real people, and I had auditions, where I did extensive improv with the actors. Then, I wrote the script based on the cast. When we were actually working on it, I gave them enough space to improvise. It was really interesting figuring out what needed to be scripted and where they could bend the rules and play. It’s like a band mentality. It’s like we’re making a song, but who knows what’s coming from where?

“I wanted to create something that made us think critically about the seemingly ‘normal’ behavior around us, while also making the everyday fantastical and thrilling to watch,” she continues. “I made the kind of theater that they would never allow in a black box.”

It’s a self-assuredness she developed in her academic life, where her professors were always encouraging her and her fellow directing students to “reinvent American theater.”

It didn’t take long for her to attract attention in Chicago. After her successful punk rendition of Faust, Lilley began to receive offers from folks like Beau O’Reilly and Jenny Magnus, the codirectors of Curious Theatre Branch, which also resides at Prop. Together, Prop and CTB produce Rhinofest, an annual fringe festival that celebrated its 30th anniversary earlier this winter. O’Reilly immediately wanted to bring Lilley into the Rhino-fold, sending her e-mails with the subject line “Because you did Faust.”

“As someone who moved to Chicago in 2013, after having only been in the underground New York scene where everything was visual- and aesthetic-based, it was really cool to find people like Stefan and Beau O’Reilly,” Lilley says. “They were making theater with their own rules. To me, the incredible thing about this work is its adventurous nature, and its willingness to craft new worlds using text, images, sound, lights, stylized physicality, music, etc.”

But it would take several years before she was able to accept O’Reilly’s invitation. In 2016 she partnered with the Minneapolis-based playwright Savannah Reich, who had written a musical called Hatchet Lady; it premiered at the 2017 Rhinofest. “We wanted to find a nice, low-stakes situation where we could work together,” Lilley remembers. “Since Rhinofest provides you the space, it was a super-homegrown, no-money operation. They’re all about building that sort of infrastructure where we are incubating all Chicago artists, redefining what new work is and what theater is.”

In 2018, after producing and directing a number of other Prop shows, Lilley was appointed artistic director of Prop. Even though the theater’s leadership hired her to be herself, she says it took some time to win over her skeptics.

“There had been other times when Prop had brought on new leadership,” she says, “but every single time, the young leaders would decide that it was too big of a responsibility and would quit after less than a year. I think also the Prop elders were worried I would kick them out or call them dinosaurs. They are not dinosaurs, but they are baby boomers, so they can be sensitive. They don’t realize the enormous achievement of managing to be serious artists for a majority of their lives. Prop is filled with people who have survived it all.”

The role transformed Lilley’s sense of self. While she was still adjusting to her new position, she wrote and directed Neverland, an ensemble-devised imagining of the final days of Peter Pan. Staged at Prop, the show received more grants than any of Lilley’s other work, and she found herself leading about 20 people at any given moment.

“I was 29, so I had to deal with the feeling of not being the youngest person in the room. There were so many years that I had to fight because of my age, but now I don’t have to anymore. It’s like, ‘What is this new evolution of myself?'”

Right now, Prop is running 2 Unfortunate 2 Travel, an adaptation of The Unfortunate Traveller, a 1594 novel by Thomas Nashe. Lilley calls it “half-conceptual art.”

“There’s some really interesting performance practices along with a strong narrative and it’s extremely visual. The entire set is entirely recycled materials.”

The show, directed by Zach Weinberg, produced by Lilley, and devised by the cast and crew, is a scathing portrayal of Jack Wilton, a world traveler and self-appointed ally of women.

“He’s trying to figure out what he can do to help, so he hires all of these women to tell his stories of his travels over the past four years,” Lilley says. The show deploys shadow puppetry, game shows, and other unorthodox devices to unravel Jack’s sense of identity while his cast of six women grapple with what it means to speak for him instead of themselves.

“To me, it reads as a criticism of the theater companies who think they can Band-Aid themselves and write about how they’re going to be diverse on their grant applications,” Lilley says.

Amid this and other critical conversations within the theater, Lilley is excited about the kinds of changes she’s seeing at Prop. She hopes to continue chipping at what she describes as Prop’s “insular” culture by keeping the door open to new folks who aren’t a part of the theater’s historic “club.”

“When I got here, everybody was friends and now they’re more like colleagues,” says Lilley. “They were resistant to clear contracts or even nailing down job responsibilities. Over the past year, everybody has really come around to valuing organization and putting that extra effort in towards communication.”

Brün echoes these sentiments, noting that Lilley has renewed the sense of professional management that had lapsed in recent years.

She is particularly good at social media to promote Prop’s work—arguably the best way of making new friends and forging artistic relationships.

“The conversation about what is exciting and experimental feels so much bigger now,” she says. “People were actually coming to each other’s shows, people who didn’t even know what this place is.”   v

2 Unfortunate 2 Travel Through 4/15: Fri-Sat 8 PM, Mon 9 PM, Prop Thtr, 3502 N. Elston, 773-742-5420, propthtr.org, $20.