Pop Spotlight

On Tuesday, August 17th, Rolling Stone hosted an exclusive screening of “Flag Day,” directed and starring Sean Penn opposite his children Dylan and Hopper. The event was hosted at the School of Visual Arts theater, and following the screening Sean and Dylan sat down for a Q&A with Rolling Stone editor Alex Morris to discuss how the film came together and what it was like working together on set for the first time.

“Flag Day” is based on journalist Jennifer Vogel’s memoir “Flim-Flam Man: The True Story Of My Father’s Counterfeit Life,” where she recounts her father John’s decades-long career of scamming and conning. Sean gave Vogel’s book to Dylan when she was 15, and the story had stuck with both of them for more than a decade.

Vogel’s work vividly describes her tumultuous childhood and complex relationship with her father who did everything from rob banks to commit arson to counterfeit vast sums of money. But there was a softer side to Frank Vogel: He was an enthralling, magnetic presence in his daughter’s life when he was around, a doting figure who could never seem to stay on track. Penn’s work behind the camera is focused on staying true to that evocative source material, and he and his daughter’s deep understanding of Vogel’s work pays off.

Dylan Penn is in a leading role for the first time in “Flag Day,” a position she handles with impressive range as she navigates playing Jenny Vogel across 15 years. “Both my parents told me that before I get behind the camera, I need to know what it’s like to be an actor,” she said, admitting that she had always had her eyes set on directing rather than acting. After years of shuffling to auditions and failing to get parts, she discovered a renewed respect for the craft and focused on developing her skills. “I realized this was serious,” she said.

The opportunity to work with her father on such a devastating portrait of a dysfunctional family wasn’t without its risks, but both actors admitted that there weren’t as many flashpoints as they expected — except for one crisis that the elder Penn brought up. “There was one two-hour standoff,” he said. “And it was over whether or not she was going to wear mascara in a particular scene or not.” (Both Penns admitted that Sean won the argument: Dylan didn’t end up wearing mascara in the scene.)

The onscreen chemistry between Sean and Dylan as Jenny and Frank Vogel suggest that this won’t be the last time that father and daughter act alongside each other — though one thing might change if Dylan Penn has her way. “I want the roles reversed next time with me behind the camera,” she said.

“Flag Day” is set for wide release on Friday, August 20th. Below is a short making-of video that explores how Sean Penn worked with his close friend and Pearl Jam frontman Eddie Vedder on the film’s soundtrack.