Chicagoan David Singer talks about his full-length feature film, “Imperfections”

Virginia Kull as Cassidy in “Imperfections.”

For David Singer, the path to directing his first full-length feature film was a circuitous one. About 20 years ago, Singer attended the University of Illinois Urbana-Champaign to study film, but was sidetracked when he dropped out after receiving a record deal. At the time, in the late 1990s, he fronted an alternative-pop band Kid Million and would go on to have a successful solo career. Since 2003, he’s been with his band Sweet Science and also has scored plays and advertising campaigns. 

Before his music career took off, Singer worked as a child actor and then as a teenager, worked for the documentary filmmaker Chuck Olin. After leaving U of I, it would be awhile for Singer to return to film but in 2013, he wrote a script with his producer-brother Jon which they turned into a 15-minute comedy called “Advantage: Weinberg,” and it received a lot of critical acclaim.

Now, Singer has just premiered his first feature length film, “Imperfections,” and is looking for national distribution. Cowritten with his brother and coproduced with Christina Varotis,  the film was shot in Chicago over 18 days, mostly on Jeweler’s Row. It is a heist story featuring a female protagonist, (Virginia Kull) as Cassidy, a struggling actress who gets caught up in a robbery scheme. She works for her mother’s boyfriend (Ed Begley Jr.), a diamond importer on Wabash as a runner or “schlepper,” which are often young woman who normally are not suspected by potential thieves of transporting diamonds to and from jewelry stores. 

You won’t see the touristy parts of Chicago in “Imperfections,” rather a focus on what Singer calls “Real Chicago.” And just as a heist film with a female protagonist is unique, it’s not the only strong female character in the film. The other is played by Chicago native Marilu Henner in the role of Val, Cassidy’s mother. In addition, Singer hired several other Chicago actors and crew members to make his film, which will be opening nationwide soon.

The Chicago Ambassador’s Bob Chiarito recently spoke to David Singer about his first feature,  “Imperfections.”



CA) A couple things stood out about this film. First, it was a story that was in your head for a long time, correct?

SINGER) Yes. About 20 years.

CA) What made you want to turn it into a movie rather than a screenplay for somebody else to shoot or just a story on it’s own?

SINGER) I went to college as a film student who left in the middle of it because I got a record deal but I always wanted to make films. I was a kid actor also. A few years ago my brother and I made a short film called “Advantage:Weinberg” that did very well. We took it to a bunch of film festivals, we took it Canne. So making films has always been something I’ve wanted to do.

CA) What made you guys make the movie in Chicago?

SINGER) We decided to come back to Chicago instead of going to Los Angeles and using somebody else’s money, we decided to raise the money ourselves punk rock style and make our own movie.

CA) Did you guys do the GoFundMe thing and other crowd sourcing sites?

SINGER) No, we just went to some people and got a bunch of investors to give us a little bit of money and we just put it into a pile and turned it into a useful amount of money.

CA) It’s cool that you have some Chicago actors like Marilu Henner.



Marilu Henner and Virginia Kull in “Imperfections.”


SINGER) Yes, and Chelcie Ross and cameos from David Pasquesi and Julia Sweeney and lots of very talented Chicago theater actors.

CA) It took 18 days to shoot?

SINGER) Yes, 18 days.

CA) I read that you wanted to show the gritty side of Chicago and avoid the typical skyline shots.

SINGER) Yes, that’s 100 percent correct. We wanted to show the city the way we know it, having grown up here. The el tracks, filthy alleys and dive bars. We wanted to show real Chicago, not the postcard version.

CA) What Chicago movies would you say are personal favorites that maybe do that for you?

SINGER) The best Chicago movie ever made is “The Blues Brothers,” by far. That is the only Chicago movie that ever really looked like Chicago to me. Now I like Ferris Bueller as much as the next guy, but that is the sanitized version of Chicago as far as I’m concerned. Also, “Running Scared” did a good job of showing Chicago.

CA) Yes. Did you ever see “Thief,” Michael Mann’s first movie?

SINGER) Yes, of course. That’s great too.

CA) There was an independent movie called “Chicago Overcoat” that filmed some scenes at Skylark that was decent.

SINGER) I don’t know that one but in our movie you’ll see The Hideout and Lincoln Square Lanes before it burned down and a bunch of places that real Chicagoans know about but that tourists never find.

CA) It just premiered at the Chicago International Film Festival. What’s the plan now?

SINGER) It will be in a few more festivals and we are currently talking to some distributors about a national release.

CA) I know you raised the money for the film on your own. Was there any hesitation from investors because you have a female protagonist?

SINGER) No, I think people recognized that we were trying to make something unique. There’s no point in doing this unless you’re trying to say something that hasn’t already been said fifty times and I think having a female protagonist in a movie like this was strangely an unusual thing. So, people were like ‘Yeah, I’d like to see that. I’d like to see something that isn’t like every other movie out there.’

CA) So it may have been an advantage in a way?

SINGER) Whatever it was they seemed to understand what we were trying to do and were supportive. Nobody gave us their opinions.



Kull and Zach McGowan.

Kull and Zach McGowan.


CA) Have you guys blown the lid off the schlepper industry?

SINGER) I don’t know, that’s a good question. I do have to say for a business that is usually supposed to be so secretive, the people on jewelers row really were incredibly generous with their time and with their ideas. We shot in 5 S. Wabash [in the Mallers Building] for eighteen days and we shot in a bunch of different jewelry stores. There’s a closeup in the movie of a diamond that’s worth $180,000. The store owner was like, ‘Come on in and use whatever you want.’ They were very generous with us.

CA) Any plans for future films?

SINGER) Yes, there’s no question. We definitely want to make the feature version of “Advantage: Weinberg” and have a bunch of other ideas as well, but first we need to get this film into the world.


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