Dylan Penn shines as a loving daughter coming to terms with her father’s shortcomings

Film | Jorge Ignacio Castillo | August 26, 2021

Flag Day
In Theatres
Opens Sept. 3
3.5 out of 5

Sean Penn may not be the easiest person to get behind, but there’s always something substantial about his work, both as an actor and director. He’s also good at subtle comedy, and not beyond parodying himself (his Exotic Birds spite store in Curb Your Enthusiasm is a classic).

Following the cinematic disaster of The Last Face (booed at Cannes in 2016, ravaged by critics, available in Prime Video), Penn rebounds nicely with Flag Day, a soulful drama about fathers not up to snuff and children coming to terms with their shortcomings.

Penn takes second billing to his daughter Dylan, who is the spitting image of her mother, Robin Wright. Dylan plays Jennifer Vogel, a bright young woman forced to navigate tricky family dynamics. Her dad, John (Penn), is a charming grifter and compulsive liar who comes and goes from her life, leaving a trail of half-baked scams, unpaid bills and broken hearts. Her mom (Katheryn Winnick, Vikings), embittered and depressed, turns to alcohol and simmers in resentment.

Following unwanted advances by her stepfather, Jen has no choice but leave home and look for her dad. While highly unreliable and often embroiled in illegal activities, John takes her in and the pair try to rebuild their relationship. But good intentions only get you so far, and Jen, after being bitten one too many times by her dad’s lies, realizes there’s something irreparable about him: a toxic mix of pride, entitlement and self-sabotage bound to bring down everyone in his vicinity.

While Hollywood scions testing their acting chops are a dime-a-dozen, Dylan Penn is the real deal. Much like her mom’s early screen appearances (The Princess Bride, State of Grace), her calm demeanour and delicate beauty conceal hidden depths and fierce determination. Her dad shows a lot more vulnerability than we’re used to, his face carved by the sun, wind and time.

Flag Day is easily Penn’s best directing outing since Into the Wild. He imbues the story (based on a memoir by the actual Jennifer Vogel) with soulfulness and humanity. Some of his decisions are questionable — like playing his character from 30 to 50-something years old, or having us believe the gorgeous lead could be a Goth outsider — but he makes it work.

Some of Penn’s friends — Josh Brolin, Regina Hall, Eddie Marsan — pop up in small roles, as does his son Hopper (it’s impossible to see Hopper and Dylan together and not think of their parents). Most notably, he brings back Eddie Vedder (whose contributions to the Into the Wild soundtrack were obscenely overlooked by the Academy) to write a couple of songs. Not to be outdone by Penn, Vedder invited his own daughter Olivia to sing lead on the first single “My Father’s Daughter”.

Even though the actors are game, Penn doesn’t dwell on the darkest passages of the story, and one can’t help but wonder if he pulled his punches because he was directing his daughter. Flag Day is powerful, but it could have been searing.