n a film he directed, Sean Penn (The Indian Runner, The Crossing Guard) picked a fine time to put himself in front of the camera for the first time. Flag Day is just Penn’s sixth directing effort and only his second since 2007’s Into the Wild, which he has openly admitted is the pinnacle of his Hollywood career. That is a crazy thing for someone who had won an Oscar for Best Actor just a few years prior (Mystic River) and again a year later (Milk). In an interview promoting Flag Day, I read that Penn had written two books and would have continued to write more had they had the same success. However, with those novels faltering, perhaps he felt directing gave Penn more autonomy than directing and that this is how he wanted his accomplishments to be with his work behind the lens rather than in front of it.

Flag Day had successful elements. The opportunity to work across from his daughter Dylan Penn (Condemned, Elvis & Nixon) for the first time was incentive enough for Penn to star as John Vogel, a lifelong conman known for drug smuggling, counterfeiting, and eluding both local and national law enforcement agencies. However, Penn’s agreement to the co-starring role only had a chance to happen when Casey Affleck bowed out after initially agreeing to sign on. Matt Damon turned the role down because he was already involved with Stillwater. It was Damon telling Penn that he’d be crazy not to play the role opposite his daughter that was the deciding factor for Sean.

While the pieces were there with Flag Day regarding the acting, the relationship between characters, and a skilled director, I wonder if this was the best story they could have told. There are thousands of true stories about the fractured relationships between fathers and daughters. While I appreciate this one’s authenticity as a true story, it needed more substance. I wanted to feel as connected to John and Jennifer (Dylan Penn) as they wanted us to be, but I never did. I wasn’t looking for a Lifetime Chanel type of movie. Penn would never give us something like that anyway. However, this story is based on the 2014 nonfiction book by Jennifer Vogel (a journalist by vocation) that fails to deliver at all the key moments.

Jennifer and her brother, Nick (Hopper Penn – Sean’s son and Dylan’s brother), had a difficult upbringing. But don’t we all? Yes, maybe not to the extent of Jennifer, but I’ve seen many other films and heard of many different stories where the impact of parents’ actions is far more significant than what we see in Flag Day (John and ex-wife Patty (Katheryn Winnick – The Dark Tower, Love, and Other Drugs)). I would have enjoyed seeing the Penn family and Winnick, perhaps in a film that brought more than Flag Day. That is not a knock on the movie, screenplay, or cast, though it’s not an endorsement. All involved did an adequate job with the source material. But this is not a movie that will wow you or have you even think about it after you leave the theater.

The Penns were great. Sean played a much more relatable character than in many of his recent films. He brings to John’s role a warmth that you would expect of a loving father. But, at the same time, he’s a conman at heart who keeps his loved ones an arm’s distance away, whether that be a physical metaphor or something more. He’s the more affable and affectionate of the two parents, and that could be seen by someone younger (or someone who is otherwise blinded) as the responsible who cares more about well-being than a more stringent and distant parent. But, unfortunately, that isn’t always the case, and, as many of us know through years of experience with our parents, it’s the long game that determines which parent is there for us more and in what capacity. And for those whose parents are divorced, the grass may seem greener on the other side of the fence. In my childhood, I had seen several friends shuffled back and forth between divorced parents. It only sometimes works out well.

Dylan plays Jennifer with much somberness. She’s looking for that adult presence in her life, especially after her drug experimentation and other struggles have taken their hold on her. Unfortunately, her parents’ other priorities (particularly John’s) outweigh the responsibility of adequately raising children to the degree that all children need to be raised. The pain and disappointment that she wears on her face and feels in her heart become more and more evident as she is rushed towards adulthood out of necessity. We feel sympathy for her but don’t feel sorry for her. She’s a fighter, and while she needed more, she did grow up loved. While she needed more, her attempts to triumph over diversity are what she’ll be able to hold in higher regard than her father’s wistful wish that he could have been something more to her.

Plot 7/10
Character Development 8/10
Character Chemistry 8/10
Acting 8.5/10
Screenplay 7.5/10
Directing 8/10
Cinematography 10/10
Sound 7.5/10
Hook and Reel 8/10
Universal Relevance 8/10
80.5%

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