Alumni Profile

Having fun at the 'Playhouse'

Amy Rubenstein '00 with her brother Joshua and husband Milan

By Caroline Cataldo

Just outside downtown Chicago, in the city’s Irving Park neighborhood, sits a small theater with a big mission: to make the performing arts relevant to a new generation of theater-goers.

Though the marquee by the front door reads “Windy City Playhouse,” those who enter are in for a different kind of theater experience, according to Amy Rubenstein ’00, the creative director and co-founder (with her brother Joshua and husband, Milan).

“People have limited time to go out socially, so when they go out, they want to get the most out of their free hours,” Rubenstein says. “We want to show you this is better than a movie. The actors are right in front of you. To sit in a room with 120 people and all laugh at the same moment is just so unique.”

windyWhen Rubenstein and her husband, who are both in the real estate business, moved back to Chicago from Los Angeles in 2010, the former actress wanted to reconnect with the city’s performing arts scene. She soon discovered that most people in the audience were much older than she and her husband.

“We want to create a theater that would be a night out of entertainment for everyone, of all ages, where you can come and have drinks before the show in a very social, laid-back atmosphere,” Rubenstein says.

The Windy City Playhouse staged four shows in its inaugural season last year, and has three more scheduled for 2016. Nell Benjamin’s “The Explorers Club” opened on Jan. 27.

After graduating from Brandeis as a theater major who took many economics classes, Rubenstein moved to Chicago to try her luck in the city’s performing arts community. She worked a few gigs doing theater, commercials and voiceover work, then moved to Los Angeles. As a means of supporting herself while she looked for acting opportunities, Rubenstein stumbled into real estate, just as the industry began to boom in the early 2000s. She built a successful business that she later merged with her husband’s. For Rubenstein, owning and operating the Windy City Playhouse requires both her business and artistic acumen.

“I did a lot of lighting when I was at Brandeis that I thought I would never use. But then, when I opened the theater and began figuring out how we wanted the lighting system to be, it wasn’t a foreign vocabulary to me,” Rubenstein says. “But I also loved my economics classes, and they were really good preparation for the business side of what I do.”

Rubenstein oversees just about every aspect of the theater’s operation, from hiring the city’s best actors and directors to purchasing lighting equipment to advertising shows.

“Working with directors now is a big part of what I do; they give me their wish list saying who they want to design their shows and how they want it to feel and I make it happen,” she says. “It was very helpful to go into the creative process knowing people work in very different ways.”

Understanding this delicate balance helps Rubenstein gain access to and the respect of the best directors in the city. The directors not only attract the top actors and designers, but tend to have the biggest followings among theater-goers.
The unique mission of the Windy City Playhouse is what keeps directors, actors and designers interested.

“They all have a love of seeing theater thrive, and that makes them buy into this idea that reintroducing theater to the next generation of theater-goers is important,” Rubenstein says. When you are passionate about something and it’s new and different and you can show a full commitment to it, sometimes people are willing to jump off a ledge with you.”

For Rubenstein, the feedback of the audience is what matters most.

“When people talk to me after the show and say, ‘This is the best theater we have ever been to, and I don’t even like theater,’ they are essentially reading our mission back to me and I feel like we have accomplished something,” she says.

Categories: Alumni Profile
Date: February 9, 2016