Word to the wise: Don’t show up late for Lookingglass Alice.

During a recent performance of the show, an oft-returning fixture of Lookingglass Theatre Company, running in its current iteration at the Chicago theatre through Feb. 15, the house manager sat some stragglers during the Red Queen’s monologue. Well, the legalistic queen (and the mischievous Molly Brennan, who embodies her) was none too pleased.

Towering above the crowd on a wheeling apparatus styled like a dress, Brennan, her vertical crimson wig as colorful as her cheeks, bellowed from above, “The rest of us started at three. I trust your departure will be timely.”

The audience erupted into laughter.

The moment was fortuitous, but once the show’s director and Lookingglass cofounder David Catlin realized what improvisational playfulness Brennan was capable of in case of an interruption, he made her scene the show’s designated late seating time. Now, if you show up after curtain, you will be repudiated by Brennan as the Red Queen.

“The sense of play that is in her eyes at all times is extraordinary,” says Catlin. “That’s what you want to be in a room with when you’re making something. That’s what you want to be in a room with when you’re watching something. Because when you play, you can believe in impossible things. And she is the living embodiment of that.”

Brennan believes there are no limits to what she can do. And if someone else wants to construct a barrier, she doesn’t see it as a constraint so much as a challenge. She’s known among Chicagoans for her physical prowess—she can walk around with someone weighing up to 150 pounds on her shoulders, as she does in Alice—and her vocal bravado, whether shouting as the Red Queen or belting (and making dirty jokes) as her cabaret alter ego Madam Barker. She has played characters young and old, male and female, classic and modern, dramatic and comedic.

Brennan has become a fixture of the Chicago theatre scene, performing in mainstage Goodman Theatre shows like Animal Crackers in 2009; in Second City revues like The Second City Guide to Opera in 2013 and American Mixtape in 2014; at Steppenwolf Theatre Company and the House Theatre; and in the city’s robust storefront scene, most recently at Red Tape Theatre in The Life and Death of Madam Barker, an original musical written just for her based on a character she created. Looks like Idina Menzel isn’t the only star having tuners penned for her.

On a Friday afternoon in Chicago’s Ukrainian Village, Brennan sits in a booth near the back corner of the West Town Bakery & Diner, sporting a red Lookingglass hoodie and jeans. Her petite stature belies her booming stage presence. At 43, she still boasts her trademark purple hair, now coiffured into a half-shaved, top-heavy whirl of a do, and an array of colorful tattoos, from comic book characters on her left thigh to dragons winding up her spine.

If there’s any trend to be discerned in Brennan’s long list of roles, it’s that many of the parts she’s played are either male or were intended to be played by a man—including the Red Queen, which was originated by Tony Hernandez. Others include Harpo Marx in Animal Crackers, her 500 Clown persona “Kevin,” Smee (played as a woman) in Peter Pan at Lookingglass in 2010, and Satan in a Second City revue. (“It totally makes sense that I would play the Devil,” she deadpans.)

“I’m a woman—I think that’s pretty clear to the world—but I have interests and energy that tend to be assigned toward what we think of as masculine. Things like a level of assertiveness and confidence and arrogance and physical strength,” she says. “Everyone has limits for all kinds of things. Most of us only have two arms and two legs. But in terms of thinking about how you move through the world and what you would like to do—how you would like to dress, how you would like to be, what you want your energy to be like—I’ve always felt it was important to encourage people to do whatever they want.”

Brennan began her journey with Lookingglass Alice almost five years ago when she was cast as the Red Queen for a touring production, which ran at Actors Theatre of Louisville, Syracuse Stage and Atlanta’s Alliance Theatre, and ended up back home in Chicago in 2010. (Brennan joined the company in Syracuse after Mitchell Fain played the role in Kentucky.)

Lookingglass producing artistic director and ensemble member Philip Smith suggested Brennan as an option to director Catlin, who admits he was only thinking of men for the role. Catlin remembered being blown away by Brennan’s physicality in 500 Clown Macbeth, which she performed at Lookingglass’s space in 2004. (The clowning troupe, semi-dormant at the moment, reinvents classic works in imaginatively gestural ways in rigorously physical and seemingly dangerous spectacles.)

That production, and Brennan’s performance specifically, reminded Catlin of the impulses that inspired him and his fellow cofounders to start Lookingglass out of Northwestern University. Their first show, before they even formed a company, was a version of Andre Gregory’s Alice in Wonderland, and it inspired the company’s name and, eventually, the current Lookingglass Alice. Bringing Brennan into the fold was a no-brainer.

“She is an incredible actor even when she’s not being asked to do something comedic or bring her clown energy,” Catlin says. “But the combination of those two, she’s just really extraordinary.”

Catlin applauds Brennan’s discipline and resilience as a performer, particularly after a rough fall she took during the show’s run in Atlanta, which knocked two vertebrae out of place. The accident happened on her birthday, and while they were resetting the show, Lindsey Noel Whiting (who was playing Alice, and now shares the role with Lauren Hirte) sang “Happy Birthday” to Brennan. Like the trouper she is, Brennan completed the performance and the show’s run. (The actor, in turn, praises how the company handled the situation, setting her up with a physical therapist and any medical attention she needed, no questions asked. There’s also a new, safer contraption for her to stand on in this production.)

And though she hasn’t taken any falls this time around, Brennan admits that age is a factor in how she tackles the show. None of the feats have changed—if anything, Catlin says, it has become more difficult, because the show is tighter and the tricks are closer together with less time to breathe.

“Age is another thing I crusade against, like gender norms,” Brennan proffers, adding that with maturity comes a deeper awareness of what her body is capable of and a need for a longer postshow cool-down. “Don’t get in the mindset of giving up, or being like, ‘I’m too old to do this.’ But like, what can I do right now? What do I want to do right now? Look at what you actually can do, not like, ‘Oh, I’m 43, I shouldn’t do this anymore.’ But like, ‘My knee hurts so I shouldn’t do this anymore,’ which is what you should also do when you’re 25.”

Brennan has always been vocal in her convictions, something she likely learned from her artistically minded, political-activist parents. But she wasn’t always encouraged to pursue her individuality. In fact, many of her college professors at the University of New Hampshire discouraged her choices. She sang Javert’s number “Stars” from Les Misérables in her musical theatre class and performed Caliban’s monologue from The Tempest in an acting class, and both times was told she’d never be cast in these roles.

“But it’s theatre! Anybody can do anything! It’s made up!” she’d plead. “We’re all in this agreement that we’re going to sit in chairs and pretend that what’s happening is happening in real time—there’s no reason to be so constrained.”

Teachers also told her to grow her hair out, to keep it a natural color and to not get any more tattoos. What she found was that ignoring all their advice led to her success.

“Me, as who I want to be, is the most marketable product,” she says. She moved to Chicago after college to pursue a graduate degree at DePaul (but left after a semester to focus on her career) and has been making a living as an artist ever since. “Doing what I wanted to do and showing what I have to offer—that’s how I got on the roll of being a professional actor, not trying to hide who I am and pretending that someone’s going to cast me as a mom in a bleach commercial. It’s just not going to happen.”

Still, if she wanted to audition for a bleach commercial, she doesn’t think there is anything stopping her. “You just show up with what you got,” she figures. “But if you decide you’re not going to try, that’s on you—you can sit there and be like, it’s totally unrealistic. Yeah, it’s totally unrealistic to be a working actor. It’s totally unrealistic to do half the shit I do.”

Education is one of Brennan’s priorities, and she just stepped down from a three-year stint as artistic director of Barrel of Monkeys, an arts education nonprofit that hosts creative writing workshops in Chicago public schools. The ensemble creates theatrical pieces based on the stories children write, which culminate in a weekly public performance called That’s Weird, Grandma.

Brennan is proud of her initiatives to bring more diversity into the 70-member company. She also introduced Chicago’s Weird, Grandma, wherein other companies from around the city, like Steppenwolf or the Hypocrites, come in and devise a show based on a kid’s story.

While she’s taking a step back from Barrel of Monkeys at the moment, education is still on her mind. One of several projects she’s working on with her collaborator (and partner) Malic White of the Neo-Futurists is Deviant Methodology, a skills-sharing instructional for people trying to make a living as artists—something Brennan strongly believes is possible.

“You can’t buy a house, maybe, unless you get a movie or you’re on a TV show all the time,” she laments, citing her “humble living” as an actor. “I don’t have a car. I rent and have a roommate. I don’t go on fancy vacations. My goal since high school has been to look forward to what I’m doing every day—that’s my goal. And if I’m working 40 hours a week at a job I hate to achieve owning a house, that’s actually just not a thing I want.”

Brennan put off joining Actors’ Equity for many years so she could continue to participate in the storefront scene, but when Animal Crackers rolled around, she finally signed on. (“I like that health insurance,” she vows, but regrets that her presence on the outskirts of the theatre scene has lessened.) With Madam Barker, Red Tape was able to negotiate an Equity deal, and certain aspects of Brennan’s work, like 500 Clown, Barrel of Monkeys and her semi-regular appearances at the weekly curated alt-cabaret Salonathon, don’t count as theatre under union rulings.

While Brennan isn’t dead set on remaining in Chicago forever, she doesn’t think she’ll be chasing a career in New York any time soon. (She does have a contingency plan, however, to start a Hollywood career in her 60s, when she can play the punk-rock grandma.) She works without an agent and lands most of her roles through calls, not auditions. She occasionally travels and has done some shows in New York, like playing Lady Macbeth and the Porter in Macbeth at New York’s Mirror Repertory Company in 2005. Her opinions about the opposite course—New York actors coming to Chicago—are pithy.

“There are companies in this town that cast out of New York not because that’s how they find the best person but because they can say, ‘We have a New York actor,’” she contends. “But the deal is, unless it’s Neil Patrick Harris, the theatregoing community in Chicago doesn’t know who they are. So it doesn’t matter! Sometimes I’m like, Who is this person? I know at least five people from here in Chicago who could do this role better!”

Brennan cites Tony winner Jessie Mueller, a born-and-bred Chicago talent who starred in Animal Crackers before the Big Apple snatched her up. “What if the Goodman had decided to get a Broadway actress to play that part?” Brennan posits.

Just because Brennan can make a living in Chicago doesn’t mean it’s easy. Art started to imitate life for her in The Life and Death of Madam Barker, an original musical with songs by John Fournier and book by Brooke Allen that was nominated for three Jeff Awards, winning two. Brennan created the character with 500 Clown in the Brecht-inspired show 500 Clown and the Elephant Deal, which played at the Steppenwolf Garage in 2009 (AT July/August 2009). An aging songstress with a drag-queen-like sensibility, inspired by the likes of Patti Smith, Hedwig (of the angry inch), Miss Piggy, Marlene Dietrich and Bette Midler, Madam Barker is a semi-deluded broad who believes she used to be famous, though she never really was.

After Elephant Deal closed, Brennan continued to explore the character by hosting gigs and holiday shows (including one with famed Chi-town chef Rick Bayless), prompting Red Tape to offer to build a production around her. Madam Barker explored the diva’s elaborate departure from show business; at the end, Brennan stripped off her Barker clothes and put on her “Molly outfit,” while delivering a monologue about the things one gives up to pursue art. She leaves the theatre as Molly, but the call of the stage beckons Madame Barker back—something all theatre artists can relate to.

“It’s about seizing your glory and going for what you believe in,” Brennan says. “People tell you that you’re too old and that it’ll never work and that your values are wrong and how it can wear you down. But Madam Barker is like, ‘Oh, fuck it, no. I’m doing this. I’m going to do this forever, and you’re going to have to drag me out.’”

Brennan concedes that her life choices don’t exactly scream role model, at least on the surface. Walking through the aisles in the grocery store, she gets many a disconcerted look from parents when their children point at her purple hair and spiked backpack with glee and desire. “I just watch the mothers wither,” she shrugs, adding that her catchphrase for friends with children is, “Don’t be like Auntie Molly!”

But there is at least one parent who couldn’t ask for a better person for his children to look up to: Catlin says his two young daughters adore Brennan, and after they first saw Alice at Syracuse, they started reciting some of her bits from the show and mimicking her actions. His older daughter even tried to dye her hair blue, to emulate Brennan’s style.

Catlin developed Lookingglass Alice partly as a love letter to his girls, and although Brennan freely jokes about many adults’ aversion to her lifestyle, Catlin made sure she knew how he felt as a father. “If my girls grow up to be like you,” he told her, “I would be really happy.”