22nd Calgary Underground Film Festival

April 17-27, 2025

12th CUFF.Docs Documentary Film Festival

November 20-24, 2024


United States, 2023: 96 minutes: Alberta Premiere
Archives 2024
In Cinema Globe Cinema
Sat, Apr 20 2:15 PM Buy
Fri, Apr 26 6:30 PM Buy


Exploring themes of art and failure, FLIPSIDE is a comical attempt to save a New Jersey record store and confront a mid-life crisis.

When filmmaker Chris Wilcha revisits the record store he worked at as a teenager in New Jersey, he finds the once-thriving bastion of music and weirdness from his youth slowly falling apart. FLIPSIDE documents his tragicomic attempt to revive the store, while revisiting other documentary projects he has abandoned over the years. In the process, Wilcha captures "This American Life" icon Ira Glass in the midst of a creative rebirth, discovers the origin story of David Bowie’s ode to a local New Jersey cable television hero, and uncovers the unlikely connection between jazz photographer Herman Leonard and TV writer David Milch. This disparate collection of stories coheres into something strange and expansive—a moving meditation on music, work, and the sacrifices and satisfaction of trying to live a creative life.

Toronto International Film Festival 2023

Chris Wilcha has won two Emmy Awards and two International Documentary Association Awards for directing and co-executive producing a TV version of Ira Glass’ acclaimed radio show "This American Life" for Showtime. He has directed promos, pilots and short films for MTV, PBS, Sundance Channel and TV Land. Wilcha also directed and shot a first person video diary called THE TARGET SHOOTS FIRST, about his tenure in the marketing department at the mail order CD and tape club Columbia House in the early 1990s, which won numerous festival awards, screened internationally, and was broadcast on Cinemax and The Sundance Channel. FLIPSIDE is his latest film.

press for Flipside

"FLIPSIDE takes viewers on a journey up river into the dark heart of the creative process where one fights the strong current of procrastination."
- POV Magazine
"It's beautiful and inspiring, and it might just spur you into some mind-f*cking self-reflection. Good luck."
- Mashable


Documentary / Music

96 minutes


Chris Wilcha

Executive Producers
Judd Apatow
James P. O’shaughnessy
Lance Acord
Jackie Kelman Bisbee
Sam Bisbee
Justin Pollock

Joe Beshenkovsky
Michelle Currinder
Alex Fisch
Adam Samuel Goldman
James A Smith
Chris Wilcha

Joe Beshenkovsky
Adam Samuel Goldman
Chris Wilcha

Adam Beckman

Ira Glass
Judd Apatow

Official website:




WINNER: Jury Award: Honourable Mention, Best Documentary Feature