5 Questions: David Singer

David_Singer David Singer

David Singer is a filmmaker/musician/writer/composer based in Chicago. His first feature film, Imperfections, was released in 2017. The Hollywood Reporter said, ““A shaggy charm permeates David Singer’s comic thriller about an aspiring actress who gets more than she bargained for upon taking a job as a diamond courier… The dialogue is frequently fast and funny… Imperfections marks an impressive debut effort from its tyro director.” His previous short film, Advantage: Weinberg, was selected for the prestigious Emerging Filmmaker Showcase at the 2013 Cannes Film Festival. 

1. What’s been keeping you up at night?
Song lyrics. I find that my best writing comes from my semi-conscious brain, and in those few minutes before I drift off I sift through melodies and little phrases and all the debris that’s built up over time. Usually I can remember stuff the next morning. But what if I’m forgetting the best stuff?

2. What’s the coolest thing you’ve seen or heard lately?
I recently stumbled upon the music of Connie Converse, and I’m obsessed.

For the uninitiated – Connie Converse was a Greenwich Village folk singer and songwriter in the 1950s whose beautiful songs barely made a dent at the time. She plugged away until the early 60s, when she moved to Michigan to work on the Journal of Conflict Resolution (kind of a lefty geopolitical magazine). She played songs for friends at parties but more or less stopped trying to “make it” in show business. She was a lonely and sort of sad lady, and when she turned 50 she sent letters to friends and family saying goodbye… and just disappeared, never to be seen again.

In 2004, her friend Gene Deitch played a couple of her songs on an NYC radio program, and it piqued the interest of a couple of listeners who miraculously found some recordings she sent to her brother in the 50s mouldering in some old file cabinet. They came out in 2009 as an album called “How Sad, How Lovely”.

It would be impossible to overstate how thrilling this music is. It’s funny and charming and sad and honest, and when put in the context of the times it was written and recorded in, it seems possible that Connie Converse was from outer space. We are now used to hearing songs that reflect the interior life and conflict of the performer, but the fact that this relatively anonymous woman in 1950 materialized this stuff out of thin air just boggles me. But that makes it sound like some sort of dry, intellectual tedium – IT ISN’T. It’s joyful! It’s funny! It’s music you can sing along to!

My eight yr. old daughter and I listen to the record together a lot and sing the songs. I told her Connie’s story, and she asked, “Do you think she’s still alive?” I explained that was unlikely, and she said, “But she could be. Maybe she’s out there somewhere being happy.” We talk about it now, and imagine all the things the 93-yr-old Connie could be doing. I hope she’s written and recorded a million songs in the 40 years since she made herself disappear, and that we all get to hear them someday.

Listen to this on a long drive:
Connie Converse Walking In the Dark

3. What’s the most exciting thing you’re working on right now?
I am writing a new movie based on an actual Chicago event in the 1970s. That’s all I can say. For now.

I’m also working on a whole batch of new songs, and I’m finally finally getting ready to make a new record.

4. If you could add anyone, alive or dead to your team, who would it be?
Albert Brooks. No one is funnier, and his best work is rooted in true humanity. I intend to spend my adult life trying to reach Modern Romance, Lost In America, and Defending Your Life and coming up woefully short. I’d like him to add jokes to my scripts and be in my movies and hang out in my basement.

More literal: My team, my one true faith, is the Chicago Bulls. I would like Michael Porter, Jr. to be a Bull next year, though I am intrigued by Luka Doncic and Marvin Bagley. If it’s living or dead, I’d add Wilt Chamberlain.

5. When the movie of your life is made, what will it be called?
“Some Of This Is True”


In addition to making films, David is a musician who has released five LPs, both solo and with his band The Sweet Science, and played hundreds of shows around the world. His records have found their way onto the Albums of the Year lists of the Chicago Tribune, Chicago Sun-Times, No Depression, Huffington Post, and the prestigious Village Voice “Pazz & Jop” poll. Greg Kot of NPR’s Sound Opinions describes David as “one of the city’s most evolved pop craftsmen of the last decade.” David is also a celebrated composer, having scored projects including August: Osage County (winner of five Tony Awards and the Pulitzer Prize) and the critically acclaimed Broadway revival of John Steinbeck’s Of Mice and Men.

For more on David Singer, check out his website, and follow him on Twitter: @dsarrows