Five essential Sean Penn roles on the eve of his new film, ‘Flag Day’


Warner Brothers Pictures

Dan Buffa, Special to the Jewish Light

“I think we all have light and dark inside us.” – Sean Penn

That goes double for actors. When it comes to performing on stage and giving a moving performance, a human being must be able to tap into the lighter and darker aspects of life –something Penn does very well in heavyweight roles. The grandson of Jewish immigrants who ran a Jewish bakery (Penn’s father is Jewish), he never takes a half-measure, and that carries over in his personal life as well.

Penn has also taken well to directing and storytelling, as evidenced in the moving true story, “Into the Wild.” His latest directorial effort, “Flag Day,” is another true story adaptation, focusing on the relationship between a master counterfeiter John Vogel (Penn) and his daughter, Jennifer (played by Penn’s real-life daughter, Dylan).

Penn’s roles are often intense and highly dedicated. Let’s talk about five of them as the actor turns 61 today.


“Mystic River”

Arguably Clint Eastwood’s second-best film, behind “Unforgiven,” this followed a group of Boston friends from their soul-crushing moment of abuse as kids, and how they grow up with it as adults. In a film stuffed with heavy-hitting work from Tim Robbins and Marcia Gay Harden, Penn stood out for his dual-sided portrayal of a man torn apart by guilt and tragedy. Everyone knows about the scene where a group (literally around 8-10 men) hold Penn’s Jimmy Markum down as he screams for his dead daughter (Emmy Rossum). For me, a couple late scenes, involving that darker side of the actor’s repertoire, are far more powerful. This film isn’t pleasant, but it’s brilliant.

“21 Grams”

Some saw this as overwrought and too dramatic but once again, that’s Penn’s thrive zone. Playing a dying math professor with a weak heart, Penn’s Paul befriends the widowed Cristina (Naomi Watts), and the two of them go on to make some painful and unfortunate decisions. Alejandro G. Inarritu’s film was challenging and dove headfirst into the emotional scar tissue of loss, but the performances, chiefly Penn’s, made this one hit extra hard.

“State of Grace”

Phil Joanau’s 1990 crime thriller about the mafia in New York City (run by Ed Harris and Gary Oldman) and the neighborhood’s prodigal son (Penn) returning in the form of an undercover cop to take it down. There’s something timeless about these old school thrillers, ones with more humanistic story threads than a simple car chase or shootout. We watch Penn’s Terry go back into his childhood streets to rekindle a friendship with Oldman’s good-hearted yet too fiery best friend and a potential romance with Robin Wright’s (who he was married to for 14 years) Kathleen, an old girlfriend. Harris is steely and cold as the mob boss, and the end delivers. There’s sadness, regret, and redemption themes mixed in with the late 80’s score and gritty look, allowing this one to hold up.


This is the movie where all of that Penn rage was dialed back considerably, making room for the tender-hearted portrayal of Harvey Milk, who became California’s first gay elected official. Gus Van Sant’s film is bittersweet for covering such a courageous figure, even if the ending is well-known. But Penn packed so much into his performance, making audiences see the everlasting impact of Milk’s actions and aspirations. It was a role that sped in the other direction, cracking into the actor’s vulnerability and sitting outside the box of his usual work. Big credit to James Franco for giving a soulfully rich performance that only empowered Penn’s role.

“Dead Man Walking”

Another role that brought the light and dark together, bringing a flame to the story of a nun (Susan Sarandon) bringing comfort to a death row convict (Penn) during his final days of life. Robbins, who would co-star and was nominated for an Oscar alongside Penn in the aforementioned “Mystic River,” directed this 1995 feature that had its own fun on Oscar night. What made it different was Penn’s Matthew Poncelet moving us around like an unsettled stomach through the film, making us care for, and also fear, him at the same time. Few actors can do that. A story that dared to tell the story of the killer while empathizing with the victim’s families. This is what you call a tour de force performance. Watch how calm, cool, and collected Penn manages to be throughout the film. Brilliant.

Honorable Mentions: “The Interpreter,” “I Am Sam,” “At Close Range,” “Colors,” “The Secret Life of Walter Mitty”

Not-So-Good: “The Gunman,” “Gangster Squad,” “U-Turn”

Say what you want about Penn’s political views or personal life shenanigans-he was also married to Madonna for a few years-but when it comes to giving an authentic performance with power attached, Penn is in a league of his own.

“Flag Day” arrives in limited theaters on Friday, Aug. 20, and opens to the public next Friday, Aug. 27.