Flag Day Sean Penn Dylan

Flag Day is little more than a Penn family vanity project

Sean Penn directs and stars in this lumpy melodrama alongside his real-life children.

Sean Penn’s directorial career never got quite the traction that his acting career (and general offscreen escapades) got, but the fact is that before 2017’s reportedly disastrous (I still have not seen it) The Last Face, he’d always made pretty good movies. Unlike his acting performances, his films tend to be subdued and a far cry from the kind of vanity project one would assume an actor as publicly vain and up his own ass as Penn would make. It’s probably worth noting, then, that Flag Day, Penn’s fifth directorial effort, is the first one in which he appears, which automatically qualifies it for a vanity status that is only exacerbated by the fact that both of Penn’s grown children, Dylan and Hopper Penn, appear in acting roles. If there was something such as an “overeager pride project,” Flag Day would be it. It tells a simple story in an overly flowery and complicated way, functioning both as a shambolic family acting reel and as a misguided, Hillbilly Elegy-adjacent attempt to understand red state Americans. 

Jennifer Vogel (played by Dylan Penn as an adult but Jadyn Rylee and Addison Tymec at other ages) has a difficult upbringing, caught between a hard-drinking mother (Kathryn Winnick) and irresponsible con man father John (Sean Penn). Though her father is generally caring towards her and her brother (played by Penn’s son Hopper Jack Penn), he’s also extremely unpredictable and prone to lying to get his way. It’s not clear exactly how he makes his living, but bikers are often seen hanging around and financially motivated moves (and/or evictions) are commonplace. As Jennifer attempts to find her path in life, her father periodically resurfaces, a reminder not only of what she was trying not to be, but also of what’s missing from her life.

A fragmented but more or less chronological look at what essentially amounts to most of a life, Flag Day is shot on grainy film stock, with Penn approximating the look of home movies through studiously sloppy camerawork. Shots take a while to go into focus, while others don’t quite focus on the right element and course-correct rapidly. Flag Day might look sloppy at a glance, but it’s clear that everything here is intentional, meant to capture a kind of rough-hewn and naturalistic side of the relationship between the Vogels. Unfortunately, there’s not much that’s naturalistic about the screenplay, which is rife with ponderous voiceover narration and tearful screaming matches between the Penns. There’s a fundamental mismatch between the type of movie Penn wants to make and what’s actually on the page that becomes increasingly overwrought as the film progresses.

Flag Day Dylan Penn
Dylan Penn in Flag Day

There’s also some level of Flag Day that appears to be about the disillusionment of the American South and the American Dream. The film is called Flag Day because that’s the day (June 14) that John Vogel was born. As his daughter explains it, John loves Flag Day because it feels like everyone is celebrating his birthday, and it instilled a sense that he was set for great things early on in his life. A little later on, John is described (by his mother, a character played by Dale Dickey who appears in exactly one scene) as railing against immigrants for taking all his jobs — something that is never really conveyed anywhere else in the movie, but somehow manages to cast the entire movie in a weirdly different light. Flag Day hardly works in a MAGA apologist framework, but there seems to be an attempt by Penn to extend an olive branch that goes nowhere.

Flag Day is ultimately about the limits and expectations of familial relationships, a theme that has recurred throughout Penn’s work as a director. Jennifer expects her father to be a loving, nurturing father even as he has proved time and time again that he’s incapable of that, while John expects Jennifer to accept his blatant lies as an inherent part of his personality. There’s a fundamental incompatibility between a man who lives only for himself and his role as a father, even if he seems quite keen on actually having a relationship with his daughter. When an aged and weathered Penn tells his real-life daughter that he truly believes people can change, it’s hard not to be a little moved. But what moves us is the context and what we know about Sean Penn as a human being — not what the movie is about and not, ultimately, what we know about Jennifer and John Vogel as characters.

Less misguided than simply shapeless and awkward, Flag Day is ultimately kind of a whiff for everyone involved. Despite best intentions, what mostly stays about both of the Penns’ performances are the histrionics, and the movie becomes a slog before it comes to its overwrought end. I’ve always liked Penn as a director and mostly liked him as an actor, but if this proves anything, it’s that maybe he should focus on one at a time. ■

Flag Day opens in Montreal theatres on Friday, Aug. 27. Watch the trailer here:

Flag Day, directed by and starring Sean Penn, with

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