By John H. Foote

(***) In theatres

Do you remember the first time you experienced Sean Penn onscreen?

I do, as if it was yesterday. But it wasn’t until the second time that I realized just how great an actor he was and was going to be. The first time was not a great role, but he was rock solid as the thoughtful young soldier in Taps (1981), best friend to lead actor Timothy Hutton. The second time blew my mind and I saw what some call “bite you on the nose talent.” Penn portrayed the stoner Spicoli in the teen romp Fast Times at Ridgemont High (1982) and walked away with the entire movie. Watching it a few weeks ago, it was astounding how little screen time he actually has, but every scene is memorable and very funny. It reminded me of going back to some of Brando’s early work and appreciating his budding talent.

The buzz about Penn spread through Hollywood like wildfire, but this was no ordinary new star. Penn was always an artist first and marched to a different drummer, just like Brando, Nicholson and De Niro. He did not care about being a star, he wanted to be an actor. He became friends with his heroes, and they mentored him. Often seen as surly, that is not the Sean Penn I have experienced in interviews, not once.

His marriage to pop star Madonna must have challenged him because they were polar opposites about celebrity: she loved it, sought the limelight, while he shied away from it, wanted nothing to do with it. That became evident when he punched out a cameraman and spent some time in jail for his actions.

His career continued to soar through the years with electrifying performances in At Close Range (1986) opposite Christopher Walken, possibly the greatest film of the 80s no one has seen, and Dead Man Walking (1995), which earned him his first Academy Award nomination for Best Actor. Two more nominations followed, for Sweet and Lowdown (1999), in which he portrayed a Depression era guitarist for Woody Allen, and as an intellectually disabled father fighting for custody of his daughter in I Am Sam (2001).

His performance in Mystic River (2003) finally won him his first Oscar for Best Actor. As a former convict who has put his life back together, though still radiates danger, Penn is remarkable in creating a devastating portrait of a father who discovers his daughter has been murdered.  The standing ovation he received upon winning the award was a testament to what Hollywood thought of his talents. Five years later he gave what is arguably his finest performance as Harvey Milk in Milk (2008), an inspiring film about the first openly gay politician in the US. Hope and joy explode out of Penn in this role, and I cannot remember him smiling so often in a film. He is astonishing. Not only did he win the Oscar but critics’ awards from the Los Angeles Film Critics Association, the National Society of Film Critics, and the New York Film Critics Circle, making his work in Milk one of the most acclaimed performances of the last forty years. His most recent outstanding performance was as a burnt-out rocker in This Must Be the Place (2012). Cheyenne (Penn) retired after two kids committed suicide causing the musician to shut down emotionally. Wealthy, living with his wife, portrayed by Frances McDormand, he strikes out to find the Nazi who tormented his father in a death camp in WWII. He draws attention to himself with his goth looks and long black hair, but he does not care and maybe that is the point. Speaking in a near whisper, Penn was brilliant in the film, which is sadly underseen and unappreciated.

In the early 90s, Penn turned to directing films every few years with his first, from a script he wrote based on a Bruce Springsteen song called Highway Patrolman, his film The Indian Runner (1991) was a Cain and Abel story about two very different brothers, beautifully acted by Viggo Mortensen and David Morse. He followed that with The Crossing Guard (1995) featuring a superb Jack Nicholson as a father seeking for the death of his daughter, killed by a drunk driver. Nicholson earned excellent reviews but sadly no one saw the film except the film critics, not enough to earn Nicholson the Oscar nomination he deserved.

Nicholson deserved another for his superb performance for Penn in The Pledge (2001), portraying a retired cop obsessed with a murder he cannot solve. With a great cast including Patricia Clarkson and Benicio Del Toro, Nicholson still towered over them all with a heartbreaking, haunting performance.

Penn’s next directing effort finally earned him greater respect and a nomination from the esteemed Directors Guild of America as Best Director for his masterful Into the Wild (2007). Based on a true story, the film explores how Chris (Emile Hirsch) drops out of society and heads for freedom in Alaska, seeking the life of Jack London. He expects to live off the land and be entirely independent of everything 20th century, but his own arrogance is his undoing, and he dies a terrible death after ingesting toxic vegetation by mistake. Penn beautifully captured the glory of nature in the film. As Chris watches wild caribou roaming the wilderness, his eyes fill with tears of joy and ours did too. It is a magnificent film, easily one of the years five best, yet the Academy sadly (disgracefully) did not nominate either the film or director. Into the Wild remains his masterpiece as a filmmaker to date. I have watched it many times since 2007 and constantly see something new in the work, with either Penn’s direction or the superb performance of Emile Hirsch, even the heartbreak in the lyrics of the songs. All snubbed!

One of the most urgent and vital American films in recent years, how does the Academy refuse to honor this work yet celebrate something like Nomadland (2020)? Is it meant to be a direct slap in the face to Penn? It sure felt like it. I know Into the Wild was not the only work of art to be snubbed by the fickle Academy, but it is certainly one of the finest achievements in film history. His reputation as a director is very much like his as an actor—authentic, fiery and honest recreations of life. Holding a mirror up to society he attempts to recreate what he sees in the reflection, for better or worse.

His last directorial effort before Flag Day was in 2016, The Last Face starring actress (and girlfriend at the time) Charlize Theron. It was savaged by critics at the Cannes Film Festival and never really found any decent reactions. Everything that could go wrong with the picture went wrong. All of his directorial efforts, except this last, feel like films that emerged through the 70s, highlighted with an integrity and truth. Obviously, the cinema influenced everything about Penn as an artist because that is where he saw the fine work of Jack Nicholson and his directing idols Sidney Lumet, Scorsese, Hal Ashby and Francis Ford Coppola. That same devotion to the truth that drove him mercilessly as an actor, drives him ever harder as a filmmaker.

Flag Day, his latest, is a fine, moving film in which he stars opposite his daughter, Dylan Penn. Both Penn and his daughter deliver strong performances that should attract audiences. With Penn, the potential for awards is always high given his talent, but if anyone is nominated for the film, it will be his daughter.

Penn portrays John Vogel, the second most prolific printer of counterfeit money in the US. He is also a loving but erratic father, who instills in his daughters a love of family. Over the course of the film we never really know if this is simply self-serving, but his daughter loves him unconditionally until she starts to question some things about him. She has always suspected he was shady, but not one of the most wanted criminals in America. As a child, she could not grasp why he would disappear, leaving his distraught wife destitute while he was off to the next scheme. But then he would seek them out, needing them to play a role in his latest scheme, and his daughter was always there for him.

Vogel is a man fueled by his own desperation, perhaps knowing the police were just a short distance behind him. The film opens in 1992, with him being arrested for counterfeiting more than $22M. From there, we are told the story in flashbacks, and it is largely the story of his daughter Jennifer, who adores her father and believes he loves her. But those lines become blurred as she grows up. Dylan Penn plays the oldest version of the character, with flashbacks played by Addison Tymec and Jadyn Rylee. Dylan Penn is a revelation, perhaps not surprising given who her parents are. Sean Penn and Robin Wright were together several years, and Dylan seems to have been born with the dramatic gifts of both parents.

Penn’s John Vogel is an exciting man, the kind of father every young kid would want, carefree, and reckless, even dangerous. By all accounts, he is a pure criminal, with a saving grace being his love for his daughter. As she grows up and becomes a journalist, Jennifer learns more and more about her father, and does not like what she finds, but loves him no less. She learns he is a conman and fears she has been conned her entire life. Imagine realizing the man you love best in the world is a crook? Would that mean he loved you less? Of course not, and she justifies his actions as best she can, stating he had “a misguided sense of pride” which drove him to do what he did.

The film can be confounding at times because, as a father, I wanted Penn just to leave Jennifer alone, let her live her life. But he cannot do that, and she does not wish him to do that. There are powerful confrontations between the pair, one electrifying sequence when Jennifer catches her father talking to a salesman on a phone that is not even plugged in. It is often a tough watch, but family stories are rarely not. Families are messy and life is messier.

Though John hurts and wounds his daughter constantly, she cannot help but love him because she is absolutely aware he loves her. For all his schemes and crimes, the love he has for his daughter is indisputable. You can feel the love in his eyes when he sees her, the regret he has for the hurt and pain he has caused her, and the pride he feels in what she is becoming, elevating herself out of the life he provided.

Both actors are sublime, Sean Penn portraying another criminal, scamming his way through life at the expense of others and unapologetic for it. It is a fine portrayal of a man who tried to grasp the American dream but did so with filthy hands seeking the easy way to it. But Dylan Penn steals the movie, and anyone who steals a movie from Sean Penn is a major actor. She is sublime as Jennifer in her late teens and twenties, slowly realizing what her father is and what he has done to her. I found myself wondering if the movie was allegorical, with Penn apologizing to his child for being who he is, despite the fine lifestyle he has given her, but sorry for all the baggage that has come with his celebrity. Regardless, he may have given his daughter the chance at an Oscar.

Josh Brolin has a small role as John’s brother, who ends up caring for the kids a lot. I liked his performance very much and wished we saw more of him. I believed that he and Penn were brothers.

Penn’s direction is, as always, unobtrusive and subtle, though he is given to a couple of dramatic flourishes that give him and his daughter opportunities to shine. Was this also intentional to allow his daughter a spotlight? Never doubt the love of a father.

Flag Day is not the masterpiece I hoped it might be, Academy Award attention will be minor, but it is a solid work from a gifted director with actors at the very top of their game. How I wish the screenplay had been up to the talents of the artists.

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