[Editor’s note: While your Flavorwire editors take a much-needed holiday break, we’ll spend the next two weekends revisiting some of our most popular features of the year. This post was originally published on April 27, 2011.] Before A Clockwork Orange, Lolita and Dr. Strangelove, director Stanley Kubrick worked as a photojournalist for Look magazine, supplementing his wages by hustling chess at Washington Square Park. A poor student and a talented photographer, Kubrick brushed off his forced experience with formal education and went for the goal. He freelanced for Look while still in high school before being hired on permanently. In the summer of 1949, the magazine sent Kubrick to the Windy City to shoot for the story “Chicago City of Contrast.”

Contrast is what he delivered, from the racial context of the economic divide to the rigid feminine and masculine roles in the workplace to changes in transportation. Flip through a bittersweet gallery of young Stanley’s dramatic Chicago.

Courtesy Stanley Kubrick.

[via How to Be a Retronaut via Metkere]

Courtesy Stanley Kubrick.

Courtesy Stanley Kubrick.

Courtesy Stanley Kubrick.

Courtesy Stanley Kubrick.

Courtesy Stanley Kubrick.

Courtesy Stanley Kubrick.

Courtesy Stanley Kubrick.

Courtesy Stanley Kubrick.

Courtesy Stanley Kubrick.

Courtesy Stanley Kubrick.

Courtesy Stanley Kubrick.

Courtesy Stanley Kubrick.

Courtesy Stanley Kubrick.

Courtesy Stanley Kubrick.