Flag Day ★★★

Director: Sean Penn

Cast: Dylan Penn, Sean Penn, Regina King, Katheryn Winnick

Release: January 28, 2022 (UK)

Every so often, an actor comes along who has made a significant contribution in making fantastic films for most of his life, then will pop off for a little while to sit in a director’s chair and see if they can make a difference in that role change instead of their usual one.

Sean Penn stepped into his directorial debut long before making films like Carlito’s Way, Dead Man Walking, and Mystic River with a little gem of an indie movie called The Indian Runner. Not long later, he gave us The Crossing Guard with his long time friend Jack Nicholson which they both enjoyed so much they went for a second round with The Pledge. It wasn’t until Into the Wild in 2007 that Penn actually got to experience some box office success and some award nominations to go with it.

Yet Penn still seems or at least feels like a bit of a myth in the Hollywood bubble, shying away from the spotlight and pops up every so often to do work that clearly means something to him. His latest directorial film comes in the way of Flag Day based on the book Flim-Flam Man by Jennifer Vogel, played so eloquently by Penn’s very own daughter Dylan Penn.

The story charts Jennifer’s strained relationship with her dad John Vogel played by Penn himself, charting two, maybe three decades of a broken father and daughter connection. A brave choice to use your own daughter for such a film and a perfect one as Dylan more than shines in a harrowing journey in accepting her father is a burden to society, though at the same time is the real hero of her heart.

The direction at times is exquisite, but the story is problematic in that it doesn’t know where to go. It would have suited the narrative better if the film was told in multiple flashbacks instead of just what is revealed to us from the beginning, leading to where Jennifer’s life takes her. Its moments like this that holds the story back from reaching its full potential.

The momentum loses itself with these dream-like sequences recalling Jennifer’s early years with her father, dragging scenes with what seems like overlong music videos that once it finally catches up to present day, its already too late for Flag Day to fully let you in.

Conisdering all the tools and talent at Sean Penn’s disposal, you’d expect more from a man who is capable of more significant expectations. Make no mistake, he can direct and does it well. Having said all this, to have him back in the room again making new material is a warm feeling. This is also the first time Penn has starred in a film he has directed.

There are a few star cameos in the film which I shall leave for you to find out, but they were not expected, and the return of Eddie Vedder was a pleasant surprise. Who thought he could better a REM classic?

When accepting his Oscar for Milk, Sean Penn once said, “I know how hard I make it to appreciate me often”. Well Sean we do appreciate you, and we do so much. We would like to see more of you, so let’s start with that.