Chicago Improv Was Dead. Can New Leaders Revive It?

CHICAGO — Fourteen months after iO Theater closed its doors because of the pandemic, a move that seemed temporary at the time, the storied improv center looked as though it had been frozen in time, the calendar stuck on March 2020.

In front of one stage, chairs were arranged around small round tables covered with a layer of dust. A grocery list in a back room reminded employees to buy more olives and baked potatoes. In the hall, handwritten signs directed audience members where to line up for shows.

“This hallway used to be so crowded that I’m sure it was a fire-code disaster,” Charna Halpern, the theater’s co-founder, said as she surveyed the barren corridor recently.

In June 2020, Halpern decided that the hallway would stay empty. The theater’s income had plummeted to zero amid the shutdown, bills were piling up and nearly 40 years after she helped start iO, Halpern announced that she was ready to close it permanently.

The theater wasn’t the only one in an existential crisis. That same month, performers of color there and at Second City — the two most prominent improv institutions in the city, where the modern version of the art form was born — spoke publicly about their experiences with racism, inequity and a persistent lack of diversity at the theaters.

Then, less than a week apart, both iO and Second City were put up for sale, heightening anxiety among performers who were already worried about improv’s post-pandemic future. Could improv be saved in the city where aspiring comedians flock to learn and perform, as stars like Tina Fey, Stephen Colbert and Keegan-Michael Key had?

The short answer is yes. Less than a year after the businesses went on the market, buyers who believe in Chicago improv stepped up. Both are industry newcomers: Second City is now owned by a New York-based private equity firm and iO by a pair of local real estate executives.

Decades of history and cultural relevance are part of what made these theaters appealing acquisitions, but after calls for transformational change, a new era of leadership is now grappling with how much of the old improv culture they want to preserve and how much they are willing to give up. At iO, criticism of its lack of racial diversity and equity has gone unaddressed during the theater’s year of uncertainty. And although Second City is back with regular shows and a plan to transform itself into an antiracist company, there is some skepticism among performers and students that this effort at reform will be different than previous attempts (a diversity coordinator has been in place since at least 2002, for example, and a revue with a notably diverse cast ran in 2016, though all the performers of color quit before it was over).

“We want it to be good; it’s our home,” said Rob Wilson, an improviser who has been in Chicago’s comedy scene for a decade. “You’re going to give them the benefit of the doubt, but you’re also not going to be afraid to leave if it goes south.”

Second City’s New Beginning

Last fall, when Jon Carr, an improv veteran, was named Second City’s new executive producer — the company’s top creative role — his peers asked him the same question: “Why did you take that job?”

The 62-year-old institution had just been the subject of a deluge of complaints from performers of color, who told stories of being demeaned, marginalized, tokenized and cast aside. As a result, the chief executive and executive producer, Andrew Alexander, abruptly resigned that summer.

Still, Carr decided to take the offer, making him the second Black executive producer in the company’s history. (The first was Anthony LeBlanc, who had served in the role on an interim basis after Alexander’s resignation.)

Carr told the people who had asked about the job that despite the pressure and inevitable stress it would bring, it presented an opportunity to change a company whose leaders had already pledged to “tear it all down and begin again.”

“This is the thing that people will be talking about 40, 50 years from now,” he said. “We have the opportunity to shape that history.”

Sitting in a booth at Second City’s restaurant in Old Town a week after the company reopened in May, Carr and Parisa Jalili, the chief operating officer who had been promoted amid the criticism, ticked off some of the steps the company had taken to meet the calls for change.

It documented the complaints and hired a human-resources consulting firm to evaluate them; it re-evaluated the photos in the lobby extolling mainly white performers and labeled offensive sketches and jokes in its expansive archive; it put into writing what the company is looking for in auditions to try to prevent bias in the process.

​​“We were able to do it all quickly because we were much smaller and more agile being shut down,” Jalili said.

The company also had to ensure that it survived the pandemic. Online improv classes were made permanent, raising revenue by opening up the potential customer base to the entire globe, rather than to only those who could show up to their sites in Chicago, Hollywood and Toronto. Then, in February, Second City was acquired by a private equity group, ZMC.

The deal made some performers even more skeptical that Second City could return better than before. What would it mean for the company to be owned by an investment firm with no track record in comedy?

Jordan Turkewitz, a managing partner at ZMC, said in an interview that the firm’s role as an investor was not to dictate decisions or get involved in minutiae; it’s to ask questions, offer advice and financially support the company’s growth.

iO Theater, Resurrected

Second City is holding several live shows a week, but for iO, a reopening is much further out.

Many employees are desperate to return, said Scott Gendell, a real estate executive who bought iO last month with his longtime friend Larry Weiner. But there is no clear reopening date on the horizon, he said.

Right now, the new owners are taking it slow, interviewing operating partners who will help run the theater and control its creative side.

“We’re being very delicate and very cautious about reopening because you don’t want to crash and burn,” Gendell said.

Gendell is the type of lifelong Chicagoan who can’t stand seeing the city’s trademark businesses shut down (“I’m still ticked off that Marshall Field’s went away,” he said). When he heard that Halpern had put iO up for sale, he and Weiner decided to buy it to preserve what they view as an important cultural institution.

But some performers are interested less in an iO preserved in amber from 2020 and more in an iO that embraces radical change when it comes to diversity.

On June 9, 2020, five improvisers who had taken classes or performed there posted a petition calling on the theater to address entrenched problems of institutional racism. They told The Chicago Tribune of “bungled or inadequate past efforts at diversity, an unwelcoming attitude to performers and students of color, and problematic behavior by staffers.”

The five improvisers pledged not to perform at iO until its management met a series of demands, including hiring a diversity and inclusion coordinator.

The next day, Halpern sent a note to the protesters offering a broad and earnest apology for the institution’s “failings.” But just over a week later, Halpern announced that iO was shutting down, frustrating performers who thought the theater was on the verge of substantial change. Halpern said the reason was the financial implications of the pandemic — not the protests.

Gendell said he was not ready to outline a plan for addressing these concerns before they brought on an operating partner but said that they were searching for partners in “diverse communities.”

“We’re fair-minded people, and I have confidence in my value system,” he said.

Performers Choose Their Own Paths

If iO and Second City want to fix the problems that have plagued them for decades, both institutions will need to convince comedians of varied backgrounds that they are places worth returning to.

In June 2020, as the stories of discrimination became public, Julia Morales, a Black Puerto Rican comedian who had performed at Second City and iO for years, thought to herself, “These theaters have really disappointed me. Do I want to go back to this?”

Her answer was to create something new. She scrounged up less than $2,000 and started Stepping Stone Theater, a nonprofit that she imagined would focus more on supporting performers of color and less on the bottom line. It is one of a few new improv ventures that have sprung up in the city in the past year.

So far, Morales has chosen to maintain some ties with Second City. In May, she was onstage improvising in the company’s first post-pandemic program, and next month, her group and Second City are collaborating on a show. Even though the theater had disappointed her, she said, she didn’t think the way forward was to shut it out.

Others, like the comedians Shelby Wolstein and Nick Murhling, have left Chicago to find opportunities in Los Angeles or have given up on big comedy institutions altogether. And some who have chosen to stay are unconvinced that there has been substantial change.

“I won’t trust it until I see it for myself,” said Kennedy Baldwin, who started last month in a Second City fellowship that offers tuition-free training to a diverse group of actors and improvisers.

Among performers who are intent on seeing the institution change, it is crucial to diversify the audience as well, which tends to skew older and whiter. These performers aren’t thrilled with the new ticket pricing system, which Second City started testing shortly before the pandemic.

The system, called dynamic ticket pricing, calculates prices based on the time of the show and number of tickets left. The cheapest tickets cost $25 each, but with growing interest in the return of live theater and lower-than-usual ticket inventory because of the pandemic, they can run much higher. This Saturday, tickets for the 7 p.m. shows are about $90 each.

Some performers worry that raising ticket prices will help maintain the status quo.

“How can I make this a show that makes people feel included and have an audience that reflects how we look?” asked Terrence Carey, a Second City performer who is Black.

A spokeswoman for Second City, Colleen Fahey, said the ticket pricing model is helpful in allowing the company to recoup revenue after a 14-month shutdown. She added that customers still have access to cheaper tickets.

At iO, Olivia Jackson, one of the creators of the petition, said she was eager to meet with the new owners to discuss the issues her group raised. After that, she would determine whether to return to iO. If she decided against it, she could always turn to one of the newer, scrappier operations.

“There are so many insanely talented people in Chicago who really love improv,” she said. “Chicago improv will be OK.”