Flipside is a 2023 documentary directed by Chris Wilcha and produced by Deep Cut Media. It had its world premiere at the Toronto International Film Festival in September 2023, screening in the TIFF Docs programme.
The film follows Wilcha — director of the acclaimed 1999 documentary The Target Shoots First — as he returns to Flipside Records in Pompton Lakes, New Jersey, a record store where he worked as a teenager that has remained almost completely unchanged for decades.
The film weaves together footage from Wilcha's abandoned projects — including a documentary on legendary jazz photographer Herman Leonard, a would-be portrait of This American Life creator Ira Glass, and the story of the record store itself — into a philosophical meditation on unfinished work, middle age, and the elusive line between failure and a life well-lived. Judd Apatow, who had lured Wilcha to Los Angeles years earlier, appears as executive producer and onscreen subject.
"A borderline-profound and philosophical expression of satisfaction with everything that is unfinished in life." — The Hollywood Reporter, TIFF 2023
"A perfect, wondrous B-side collection — filled with the ideas you wished had become singles." — IndieWire, TIFF 2023
"It's beautiful and inspiring, and it might just spur you into some mind-fucking self-reflection." — Film Daze, TIFF 2023
"A moving, funny, inventive film that may cause viewers to follow Wilcha's lead and ask tough questions about their own lives." — The Film Stage, TIFF 2023