Composite of five drag performers of color
Featured drag artists in Free Street's streaming Radical Love benefit. From left: America Powers, Haba Nero, Lúc Ami, Stephanie Gato-Girl, Cindy Nero Credit: Courtesy Free Street

Free Street Theater was founded in 1969 by Patrick Henry, an alum of the Goodman School of Drama whose vision was to create a multiracial ensemble that could tour neighborhoods and break down “the artificial barriers that divide us.” That mission has remained intact through many changes of leadership over the past 53 years and through the challenges of the pandemic shutdown of the last two years.

On Saturday, Free Street presents its seventh annual fundraiser, Radical Love: Radical Survival, as a livestreamed lip sync battle featuring digital performers as well as prerecorded submissions from community members. This is the second consecutive year that Free Street has gone virtual with their benefit. But Free Street executive director Karla Estela Rivera points out that just because it’s online, that doesn’t mean it’s not representative of the communities Free Street serves.

Radical Love: Radical Survival
Sat 3/12, 7 PM, streaming via, $10.

One of the company’s goals, says Rivera, is “eliminating the geographic and economic barriers to experiencing theater. We can’t all be together, but we can be together in community in this way.” After a successful digital outing last year (and consistently presenting digital content, both archival and original, over the past two years), she says that this year’s benefit celebration “took it up a notch. And what I mean by that is that we kind of built it more intentionally. Cindy Nero [Sebastian Olayo], who is also a teaching artist with us and the codirector of our upcoming show, 57 Blocks, is an active drag queen and digital drag queen who comes from the community.” 

She adds, “We wanted to highlight queens and kings that not only came from the communities, but are often not necessarily in the more mainstream drag scenes. Which is not my experience, but from their experience is very political in terms of how you get into shows like that.” In addition to Nero, the celebration includes performances from America Powers, Lúc Ami, Haba Nero, and Stephanie Gato-Girl.

Rivera joined Free Street just a few months before the 2020 shutdown. “When shelter in place first started, we were very close to opening Wasted. It was slated to open live. We had never imagined the idea of shutting it down. We saw a lot of our contemporaries just canceling shows. With a core team of three staff [Rivera, artistic director Coya Paz, and director of education Katrina Dion], we came together and we just knew that we didn’t want to let people down.” The company presented the story of environmental justice as a digital play in summer 2020.

“A budget is a moral document,” adds Rivera. “It reflects what your priorities are as an organization. We knew that we did not want to just cease to produce the show. Our young people, our ensemble, had put so much work into it. Katrina had put so much work into it. And we also knew that our artists who were involved in the project and the artists that weren’t yet involved in the project were looking at income insecurity in a really big way. Our 1099 friends really bore the brunt of the economic catastrophe of COVID. Specifically in the arts.”

By switching to digital and expanding their programming reach, Rivera points out that for fiscal year 2020, “We executed over 200 artist contracts.” The starting pay for all artists at Free Street, including the youth ensembles, is $15 an hour.

Though their headquarters are in the fieldhouse at Pulaski Park in Wicker Park, Free Street has been expanding to other neighborhoods, and not just with touring work. In spring of 2017, they opened the Storyfront theater in Back of the Yards, originally in order to produce longtime Free Street associate Ricardo Gamboa’s Meet Juan(ito) Doe. During the shutdown, that space (a former refrigerator repair shop once owned by a Mexican immigrant, Jose Guadalupe Ornelas Guerra) served as a community pantry. 

With 57 Blocks, Free Street’s two youth ensembles at Pulaski Park and Storyfront combine their voices. “57 Blocks began as a digital project,” says Rivera. “There’s always a silver lining, even when things are challenging. And the silver lining for us was that because of the Zoom platform and because of online platforms, we were able to bring both youth ensembles together to create one solitary piece. With our process, we work with our ensembles to identify the stories and the challenges that they face living within our Chicago communities. What emerged was the theme of education and the pathways and the pipelines that are currently existing for them. And then they began reimagining what the world could be in education, if it really serves them.”

She adds, “Audiences can expect a really fabulous journey where they begin at our Pulaski Park location for the first part of the play, and then we put them on a bus, literally on a bus, and the play continues down Ashland Avenue to the Storyfront, where they complete the show in an immersive experience.” 

The company is partnering with the Liberation Library, which sends books to incarcerated youth in Illinois, and is also connected to the Final Five Campaign, which is dedicated to closing the last five youth prisons in the state. But Rivera notes that 57 Blocks, just like Radical Love, is also a joyous celebration of communities that are often overlooked when we talk about the arts in Chicago. The show is slated to open in summer 2022.

As for the challenges still ahead? Rivera points out, “I think Free Street and other arts organizations that are doing a whole lot with a whole little are always applauded for how we deal with scraps. And we know everyone’s amazed at what we’re able to do, but it really is about a simple realignment of what the priorities are and what the challenges are, and what our mission is.” With Radical Love, they hope to be able to raise a few more dollars to support that mission.

Changes at Second City, Chicago Shakes, and Oak Park Festival

Second City has been through a number of personnel upheavals since June 2020, when longtime owner, CEO, and executive producer Andrew Alexander resigned in the wake of growing online criticism of institutional racism at the comedy giant. Anthony LeBlanc served as interim executive producer after Alexander’s departure. In early December 2020, Jon Carr, a veteran of the improv and sketch scene in Atlanta, came on board as permanent executive producer. 

But late last month, Carr announced he was stepping down. According to a Sun-Times report, Julia Dumais Osborne, managing artistic director of the Second City Training Center, told staff in an email that Carr left “due to changes in his personal life.” No word yet on who is in the running to succeed Carr. Second City itself was acquired a year ago by private equity firm ZMC.

Barbara Gaines Steve Leonard

Barbara Gaines, the founder and artistic director of Chicago Shakespeare, announced on March 1 that she will be stepping down in 2023. Gaines founded the company in 1986, when they performed Henry V on the roof of the Red Lion Pub in Lincoln Park. By 1999, they had moved into their spiffy digs at Navy Pier, where Gaines and executive director Criss Henderson expanded the international profile of the company with tours to Europe and with the WorldStage series, which brought troupes and artists from around the globe to Chicago (a successor of sorts to the defunct International Theatre Festival of Chicago). In 2017, the company opened the $35 million flex-use space, the Yard, which is where the Broadway hit production of Six, a sassy rock musical about the wives of Henry VIII, had its North American debut. (Six returns in a Broadway in Chicago touring production at the end of this month.)

Gaines’s announcement comes a few months after Goodman artistic director Robert Falls announced his retirement, which is effective later this summer. With their departures, the artistic directors with the longest tenures in Chicago are B.J. Jones at Northlight (which is planning a move from Skokie back to a new building in downtown Evanston) and Charles Newell at Court Theatre.

After a disastrous fire in their offices late last year, Oak Park Festival Theatre is moving forward; they’ve brought on Tom Arvetis as their new managing director. Arvetis ran the youth-oriented Adventure Stage Chicago for nearly two decades, and is a resident of Oak Park, where OPFT has produced outdoors in Austin Gardens for nearly 50 years. The summer 2022 season has yet to be announced.