Twenty-five years later, Lookingglass Theatre Company has gone from producing small storefront productions to a Tony Award-winning player in the city's arts community. And Schwimmer has returned to direct the company's summer offering, a crime comedy called "Big Lake, Big City" written by Keith Huff of TV's "Mad Men" and Broadway's "A Steady Rain."
Chicago is where Schwimmer comes to be creative.
"For me, it is my artistic home because of the company ... more so than anywhere," Schwimmer said, wearing a baseball cap and eating sushi during his dinner break while working on "Big Lake, Big City," which runs through Aug. 25.
Schwimmer was one of eight theater students at Northwestern who started Lookingglass in 1988. They were all working odd jobs, trying to make a living as actors and focusing on the company, Schwimmer said.
"We would be paying dues to the company to keep it afloat," he said. "We had crazy things, like if you were late for rehearsal—and mind you these were rehearsals no one was paid to attend—but if you were late you would have to pay $1 a minute that you were late and that went right to the company."
That discipline and focus was needed in Chicago's competitive theater environment, Schwimmer said. The company's first few seasons featured heavy material—a production of "The Odyssey" and Schwimmer's co-adaptation of Upton Sinclair's "The Jungle."
Schwimmer, 46 and now married and the father of a 2-year-old daughter, went on to "Friends" fame a few years later, but he still worked with Lookingglass.
"I made a deliberate effort to stay connected, to direct and to act," Schwimmer said. "I would say it was the same as my relationship currently with the company."
That includes working on a production every two years, helping with fundraising and attending yearly retreats where the company decides on the next season's projects.
"What I love about our company is that no one person has any more pull than anyone else," Schwimmer said. "Every play I propose—like any other director, any other company member—is subject to democratic vote by the company."
But Schwimmer does have something more to offer Lookingglass: Hollywood celebrity.
Schwimmer was instrumental in helping the company get meetings with the Chicago mayor's office and Illinois governor's office, which made it possible for a permanent space in the historic Water Tower Water Works building on Michigan Avenue in 2003, said Andrew White, Lookingglass' artistic director.
"The name 'David Schwimmer' would open doors that would ordinarily not be open to us," White said. "His hit status helped at a time when the organization was ready to take that leap. He's a strategic enough thinker so he knew that was the best way he could be of service."
Schwimmer has felt support from Chicago, too. Lookingglass earned nods from actor John Mahoney, known for his role on "Frazier," and the late actor and activist Studs Terkel. Schwimmer describes Chicago's Steppenwolf Theatre Company an older sibling.
"The community here is really truly supportive of each other," he said. "Of course there's a healthy spirit of competition but the idea is not to rub out the competition."
White, who was one of the original Northwestern students who helped found Lookingglass, said the company provides Schwimmer with a place to take risks.
"It still feels like that quality that he always aspired to, for the audience to be leaning forward, for their breaths to be taken away," White said.
Schwimmer, who will direct Laura Eason's "Sex With Strangers" in New York next summer, said Lookingglass gives him the opportunity to work with other talented artists who have known him for decades and will offer honest feedback.
"We built something," Schwimmer said. "And you can imagine if you've been part of building something for 25 years it is your home."