Now on Amazon Prime Video, Flag Day is a true family affair: Sean Penn directs himself and his offspring in this BOATS (Based On A True Story) drama; he plays a serial con artist and lousy father for his kids, portrayed by Dylan Penn and Hopper Penn. Based on journalist Jennifer Vogel’s memoir The Flim-Flam Man, the story is told from the perspective of the Dylan character as she deals with her long-fraught relationship with her father. Previous to Flag Day’s late-2021 theatrical release and an extended cameo in Licorice Pizza, Sean had been somewhat quiet professionally, last seen in long-shelved drama The Professor and the Madman and last heard in The Angry Birds Movie, the latter being the least likely Sean Penn performance since Jeff Spicoli. This film marks his sixth behind-the-camera effort, where he’s proven himself to be a thoughtful and skilled director (Into the Wild is underrated, and The Pledge even more so), so here’s hoping Flag Day follows suit.
FLAG DAY: STREAM IT OR SKIP IT?
The Gist: JUNE 1992: A fleet of cop cars, SWAT trucks and helicopters chase a sedan down the highway. We then meet Jennifer (Dylan Penn) as a U.S. Marshall (Regina King, in strictly a cameo) tells her about her father: He skipped an arraignment and went on the run. He passed $50,000 in counterfeit currency; he printed $22 million. Jennifer asks to touch one of the incredibly convincing $100 bills, which triggers the flashbacks. Yes, this has been a framing sequence. We’ll get back to it later, because that’s what so many movies do, so very often.
Anyway. “My father came and went from our lives,” Jennifer says in voiceover, giving us eloquent impressions of her life with a man who would live and likely die in a “violent and spectacular” manner. SUMMER 1975: Jen is 11 (Jadyn Rylee). The family’s cruising along in the station wagon when John (Sean Penn) plops her on his lap, tells her to drive and then closes his eyes to take a quick snooze. He’s THAT kind of father – trusting, irresponsible, loving, living on the edge. Despite not having any money, he finagled his way into a dilapidated fixer-upper of a farmhouse for the family, rounded out by mom Patty (Katheryn Winnick) and little brother Nick (Beckam Crawford). Happy times with Dad, who’s a fun guy until he fights with Mom and takes off in a taxi, leaving the family penniless with piles of unpaid bills. Mom drinks, sleeps and frets, and that’s it, so Jennifer and Nick move into John’s neat little lake house – boating, dancing, swimming, fireworks – until some shady biker-types rough him up. So he drops them back into their mother’s lap.
MAY 1981: Jennifer is a delinquent punk-rock teenager and is back to being played by Dylan Penn. Her stepdad is an abusive shitheel, and Patty doesn’t save her daughter from him. She runs away. Greyhound bus, a night or two on the street, then she knocks on her dad’s door. He opens it and looks like a cigarette with sunglasses. A few marbles have been lost. But straightens him, and herself, out. Pleads with him to not bullshit her, and she’ll do the same. The honesty holds up for a while, but this isn’t the type of film that pivots to a happy story. I mean, we still have to get back to the cops chasing that car, and Jennifer affirming her suspicion that her dad never really stopped spiraling downward.
What Movies Will It Remind You Of?: Sean takes some of his impressionistic Into the Wild vibes and makes them extra Terrence Malickian, visually and tonally invoking Days of Heaven, Badlands and The Tree of Life – does it have sun-dappled fields of golden wheat? You’re goddamn right it does – with a con-artist character inspired by stuff like Paper Moon or Catch Me If You Can.
Performance Worth Watching: Dylan Penn shows the composure of her mother, Robin Wright, in the face of her father’s almost-too-big, on-the-verge-of-ham performance. Carrying Flag Day is a big ask – she’s 30 and was asked to play 17 for a chunk of the film – but she does so ably and with as much depth as the somewhat sketchy screenplay allows.
Memorable Dialogue: Dale Dickey (also in a cameo) says, “Never trust a bastard born on Flag Day,” and then takes a big swig of booze, possibly because she just invoked the movie title in the dialogue.
Sex and Skin: A couple moments of brief, incidental nudity.
Our Take: Flag Day is a story of wrenching plits and complicated reunions, in which Sean Penn, as the man stuck in a self-destructive cycle, goes big and Dylan Penn, as the woman trying not to get caught in that cycle, brings the endeavor back down to the earth. Until she just can’t, and the film becomes a series of increasingly hyper-melodramatic moments rendered slightly chintzy by its slightly-too-tidy literary ambitions. To grossly boil it down to simple math: 51 works, 49 doesn’t.
Sean the director does a hell of a lot of directing here, mostly for the better. Jez Butterworth and John-Henry Butterworth’s screenplay spans a two-decade story, working in voiceover narration by two characters, and a bevy of locations and bit supporting parts (Hall, Dickey, Josh Brolin and Eddie Marsan all show up briefly) that are perhaps sketches by design rather than crisply defined. Some of this works with the film’s overall evocative, melancholy tone; shooting with the coarse grain of a ’70s drama, Sean frequently uses montages as narrative shorthand, culling the wheat from the chaff, efficiently capturing emotions emphasized by a contemplative soundtrack from Eddie Vedder, Cat Power and Oscar-winning Once actor/songwriter Glen Hansard.
So Flag Day has admirable style, and plenty of it. But it’s sometimes hampered by performances that can be too, well, performative. The film’s eventually defined less by its astute visual approach and savvy editing, moreso by tearful closeups, anguished shouting and a gut-wrenching climax undermined by overwritten calculation. The heart of Jennifer Vogel’s story survives all this melodrama, but it’s a fight, a real fight, at times.
Our Call: Like its core relationship, Flag Day has many ups and downs – just barely more of the former than the latter. STREAM IT and maybe accept it for its flaws.
John Serba is a freelance writer and film critic based in Grand Rapids, Michigan. Read more of his work at johnserbaatlarge.com.