Imperfections Credit: Matthew Sperzel

 is an independent film that boasts a number of admirable qualities: an original heist story shot on a small budget, an authentic Chicago setting (viewers may recognize local haunts Lost Lake, the Hideout, and the Jewelers Row stretch of Wabash), and a 31-year-old female protagonist.

“I thought it would be interesting to have an actual adult woman as a protagonist of a movie,” says the writer, director, and composer, David Singer, who spoke to me by phone this week. “I don’t know why that’s such a left-field idea, but it is fairly uncommon.”

Singer’s polished crime caper, which makes its world premiere at the Chicago International Film Festival on October 14, is a charming, if not overt, feminist narrative. The heroine (Virginia Kull) is a down-on-her-luck actress who gets caught up in a robbery scheme. She vacillates between two men, an ex-boyfriend (Zach McGowan, Shameless) and a coworker (Ashton Holmes) of comparable dissoluteness. However, the film’s central love story is between the protagonist and her elegant, sensible mother (Marilu Henner), who often butt heads. And the thriller-comedy—Singer’s first feature, cowritten with his younger brother Jonathan and coproduced with Christina Varotsis—aces the Bechdel test.

“I have lots of strong and intelligent women in my life,” Singer says. “And it was important to me that the women in the movie be fully fleshed-out, three-dimensional characters who interact with each other and talk about things other than men.”

ImperfectionsCredit: Matthew Sperzel

The mother’s boyfriend (Ed Begley Jr.), a diamond importer on Jewelers Row, offers the daughter a job as a runner—a position typically given to pretty, inconspicuously dressed women whom no one would suspect of carrying precious stones in their pockets. 

“The idea for this story has been percolating in my mind for 20 years,” Singer says. “I have a friend who was a courier for a diamond importer and ran diamonds around downtown. It’s a real thing.”

But 20 years ago, Singer was more focused on making music than making films. He entered the University of Illinois Urbana-Champaign as an undergraduate and briefly studied film (“We were making movies on Super-8 and 16-millimeter, literally cutting and taping them,” he says) but dropped out when he landed a record deal.

Breaking out in the indie-music scene in the late 1990s with his alternative-pop band Kid Million, Singer went on to have a successful solo career, playing almost all of the instruments on his debut LP, The Cost of Living. He also scored plays: he composed the original music for Steppenwolf’s August: Osage Country and the 2014 Broadway revival of Of Mice and Men. Singer has been performing and touring with his band, the Sweet Science, since 2003. 

“When you’re 20, putting the three guys you grew up with in a van and driving around the country playing shows seems like an infinitely more achievable goal than putting together all of the money and the people and the ideas to make a film,” Singer says, chuckling. “But now I’m a grown-up and like doing hard stuff.”

David Singer
David SingerCredit: Chris Popio

Singer comes from a show-business family. His late mother, Maureen Brookman, was a prominent agent at Stewart Talent at Chicago, and he and Jonathan were child actors. “Jon was in a couple of movies,” Singer says. “I got a couple of callbacks for Kramer vs. Kramer and then didn’t get it. I did commercials, catalog shoots, and stuff like that.”

As a teenager, Singer worked for the documentary filmmaker Chuck Olin (In Our Own Hands), cataloging videotapes while Olin was making his films. 

“He taught me quite a lot about making movies,” Singer says of Olin, who died in 2005. “And there was an editor on the project at the time who was working on a film about a couple of high school basketball players, and he said it was going to be really good. The guy was Fred Marx, and the movie was Hoop Dreams.”

Singer says he returned to filmmaking in his mid-30s, writing a script that he and Jon, by now an established producer of commercials, turned into a 15-minute teen comedy called Advantage: Weinberg.

“It was a fantastic experience,” Singer says of his well-received film debut; the brothers screened the short at Cannes in 2013. “And it gave us kind of suspension of disbelief that we could make a feature film, if we just buckled down and tried to do it.”

ImperfectionsCredit: Matthew Sperzel

Singer and his crew, including director of photography Andrew Wehde (the Netflix comedy special Bo Burnham: Make Happy), shot Imperfections during 18 days in Chicago last summer. “That meant shooting eight or nine pages a day a lot of the time,” Singer says, “and these were very dialogue-heavy scenes. So it required long takes and a lot of planning on my part, and getting actors who were able to go for three or four minutes at a time without needing to call for a line. And it came together.”

Kull, a familiar face on the New York City stage and on the small screen (Boardwalk Empire, Gracepoint), was “incredible,” Singer says. “We were casting the movie and I saw a videotape that she had made of herself in a hotel room auditioning for a Bruce Norris play. And I was like, ‘I want her.'” Kull’s next gig is the upcoming HBO drama series Big Little Lies, where she’ll appear alongside Nicole Kidman, Reese Witherspoon, and Laura Dern. 

As for Singer, he will be taking Imperfections to CIFF and to the Austin Film Festival in one whirlwind week; and from there, he says, “points beyond.” He will be playing with the Sweet Science at the Hideout in December, he tells me, and will “hopefully” make a new record next year. 

“I’m just going to keep making things until they tell me I have to stop.” 

Imperfections screens at AMC River East 21: Fri 10/14, 4 PM; Sat 10/22, 8:30 PM (with actors Virginia Kull, Marilu Henner, Zach McGowan, and Chelcie Ross in attendance); Sun 10/23, 12:30 PM.