Film Review: ‘Flag Day’ Evokes Enough of Sean Penn’s Filmmaking Strengths to Overcome Weaknesses

Behind the camera, Sean Penn has had an interesting career. Early on, his intimate character dramas like The Crossing Guard and The Indian Runner (inspired by a Bruce Springsteen song, no less) hinted at some top-notch skills. The Pledge hammered that home, before a break eventually brought his directorial masterpiece, Into the Wild. Since then, something happened. The Last Face was borderline unwatchable, leading to some trepidation about Penn’s latest directorial outing, Flag Day. While it’s certainly flawed, there’s enough here to warrant a light recommendation. At its best, it evokes some of what’s come before from Penn the filmmaker. It’s not a return to form, but it’s at least a step in the right direction.

Flag Day is a showcase, more so than anything else, for Penn’s daughter. Dylan Penn is electric here, showing the sort of passion that her father possesses. That performance, as well as certain touches from Penn behind the camera, allow this to rise above its potentially generic trappings.

Based on Jennifer Vogel’s memoir, this is the story of her family, in particular her and her father John (Penn). Jennifer (Dylan Penn as an adult) worships John, who presents a larger than life figure. Throughout childhood, John’s energy made her and her brother Nick feel special, even as it pushed away their mother/his wife Patty (Katheryn Winnick). When they split, the children spent most of the time with her, leaving him to his own devices.

As Jennifer grows up, her relationship with both parents fray. Normal teenage angst puts a wall up between her and Patty, but Patty’s mistrust of John keeps him a mystery. That is, until she runs away to stay with him. There, his lies are harder to cover, though he still tries to make life an adventure for his daughter. As an adult, Jennifer grows into a respected journalist. John, however, gets into the counterfeiting game, with his delusions of grandeur destined to eventually blow up in his face, with potentially devastating consequences for his daughter.

One thing this film certainly proves is that Dylan Penn is going to be a star. She gives her all here and invests you in a complex portrayal of a woman coming to terms with not just who she is, but who her father is. The screenplay doesn’t always serve the side characters well, but it’s all-in on her. Penn is wonderful, plain and simple. As for Sean Penn, he’s good, but never goes above and beyond. It feels like a riff on some of the roles he’s played before, though keep in mind, this isn’t a bad performance. His best scenes show him crafting an adventurous world for his children. The rest of the cast is mostly forgotten about, with Katheryn Winnick never getting a moment to shine. Supporting players include Dale Dickey, Eddie Marsan, Hopper Penn, and more, while some cameos here include Josh Brolin and Regina King.

Sean Penn takes the script by Jez Butterworth and John-Henry Butterworth, which is pretty standard issue, and tries to art it up. There’s a 90’s indie film vibe at play here, done earnestly enough that it works. The writing is often on the nose, so Penn had the option of leaning into it or drawing attention away from it. By opting for the former, the flick becomes something almost vintage. It doesn’t always work, but Flag Day does always keep your interest. Dylan Penn does the rest.

Flag Day, despite its flaws, does evoke the early days of Sean Penn’s directorial outings, making for an interesting viewing. You definitely need to keep your expectations in check, but if you do so, there’s something here. Almost in spite of itself, I found it to be a compelling experience.

SCORE: ★★★