Review: Featuring Real-life Father Daughter Sean and Dylan Penn, Flag Day Explores Family Dynamics and Overcoming Traumas

Based on the real-life story of journalist Jennifer Vogel, Flag Day offers a volatile father-daughter tale that is as much about the way we love certain family members unconditionally as it is about how those same family members can be a constant source of disappointment in our lives. And often those two feelings about someone occur simultaneously over our entire life. Vogel is played as an adult by Dylan Penn, the daughter of her director/co-star Sean Penn and actor Robin Wright. The elder Penn naturally plays Vogel’s father John, one of the world’s most ambitious losers who excels in screwing up his life and the lives of those closest to him. John lies as frequently as he chain smokes, but there’s a bond between him and Jennifer that is unbreakable, and her capacity for trusting him when she knows she shouldn’t is often soul-crushing.

Flag Day Image courtesy of MGM

I normally have a low tolerance for stories about men like John, but there is something so needy and winning about Penn’s performance that even I found myself buying his lies about having money or a job or just generally being in good shape for once. The truth is, John is always in a bind, in debt and in trouble, and as a result, he had little time to raise his two children, Jennifer and Nick (played by another Penn/Wright offspring, Hopper Jack Penn). Instead, the kids are largely raised by mother Patty (Katheryn Winnick), who is a mostly good influence but turns a blind eye when her new husband frequently gets drunk and attempts to crawl into bed with Jennifer. After one of these events, Jennifer seeks out her father and the two end up living together and getting stable jobs for a time. But John seems to despise all conventional things, so when he loses/quits his job, naturally he doesn’t mention this to his daughter.

Jennifer has aspirations of being an investigative journalist and works her ass off to make that happen right around the time her desperate father robs a bank and gets thrown into jail for a number of years. There is something so fascinating about watching an actual father and daughter play these parts, and Dylan Penn has no problem going eye to eye with her father, long considered the greatest actor of his generation. Adapted by Jez Butterworth (Ford v Ferrari, Tony and Olivier award-winning play The Ferryman), Flag Day marks the first time Sean Penn has directed himself in a film, but clearly getting the opportunity to direct his kids in this movie was something he couldn’t pass up. With a handful of great supporting roles by Josh Brolin, Dale Dickey, Eddie Marsan, Regina King, and James Russo, the movie has no trouble selling us on the destructive powers that familial bonds can sometimes have, but Vogel’s story is one of triumph, overcoming, and taking the best parts of her father and making them an integral part of her skill-set.

The icing on the cake here is the soundtrack, loaded with contributions from Pearl Jam’s Eddie Vedder, Glen Hansard (from Once), Cat Power, and even Vedder’s daughter Olivia, who helps underscore the father-daughter themes of the movie. Flag Day is often self-indulgent, and Penn frequently lets scenes go too long to the point of embarrassment. Strangely enough, it’s often Dylan who saves the day and brings the sequence back on track or finds a way to end it on a sobering note. If you see the film for no other reason, check out Dylan Penn’s first true calling card as a resilient, powerful actor who finds a way to improve her father’s work by getting to the core of an inspirational character while keeping her fully grounded in the flawed and fragile life in which she grew up. It has its problems, but Flag Day's strengths are many and worthy.

The film is now playing in theaters.

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Steve Prokopy

Steve Prokopy is chief film critic for the Chicago-based arts outlet Third Coast Review. For nearly 20 years, he was the Chicago editor for Ain’t It Cool News, where he contributed film reviews and filmmaker/actor interviews under the name “Capone.” Currently, he’s a frequent contributor at /Film ( and Backstory Magazine. He is also the public relations director for Chicago's independently owned Music Box Theatre, and holds the position of Vice President for the Chicago Film Critics Association. In addition, he is a programmer for the Chicago Critics Film Festival, which has been one of the city's most anticipated festivals since 2013.