Sean Penn: A Career in Focus

25 Jan 2022 | 8 MINS READ
Sean Penn: A Career in Focus
Ian Haydn Smith

Actor Sean Penn has sporadically turned to directing over the course of the last three decades. Flag Day is his latest and continues a style that draws on a golden age in independent-minded American cinema.

Actor, filmmaker, activist, provocateur and hell raiser, Sean Penn has enjoyed a colourful and occasionally controversial career. He has often divided critics. His relationship with the media is frequently prickly and, on the odd occasion, has even become physical. He is opinionated, polemical and unapologetic in his views and statements. An iconic outsider in his early work, in later life Penn has embodied a wide range of characters, both on- and off-screen.

For many, Penn remains Jeff Spicoli, the surfer dude in Fast Times at Ridgemont High (1982), stealing the entire film with his hilarious stoner performance. He embodied a rebel spirit in The Falcon and the Snowman (1985) and At Close Range (1986), an image bolstered by his outrageous real-life antics and marriage to Madonna. They went on to make Shanghai Surprise (1986) together, one of the less celebrated vanity projects of the 1980s. Fellow rebel Dennis Hopper recognised a kindred spirit in Penn and cast the young actor as a tearaway cop in the controversial LAPD drama Colors (1988).

The 1990s saw Penn come into his own. After a solid starring turn in State of Grace (1990), he held his own as a sleazy attorney opposite Al Pacino’s ex-con in Carlito’s Way (1993) and impressed as a convicted killer on death row in Dead Man Walking (1995). He was understated in Hurlyburly and The Thin Red Line (both 1998), before ending the decade with his most atypical and charming performance, playing the world’s second greatest jazz guitarist, in the bittersweet comedy-drama Sweet and Lowdown (1999).

Excluding the wearisome I Am Sam (2001), which was hilariously parodied by Ben Stiller in Tropic Thunder (2008), Penn’s acting in the 2000s became increasingly charged. Following an eccentric turn in It’s All About Love (2003), the actor blazed his way to his first Best Actor Academy Award, playing a grieving father in Mystic River (2003). In the same year he impressed as a dying mathematician in 21 Grams. If his performances in The Interpreter (2005), All the King’s Men (2006) and Fair Game (2010) were solidly impressive more than inspired, he was superb playing assassinated San Francisco councilman Harvey Milk in the moving biopic Milk (2008), for which he received his second Academy Award. Since then, roles have ranged from the oblique (The Tree of Life, 2011) and the bizarre (channelling The Cure’s Robert Smith for 2011’s This Must Be the Place) to the caricatured (hamming it up as real-life mobster Mickey Cohen in 2013’s Gangster Squad) and humdrum (playing a hardman in 2015’s The Gunman, which he also wrote).

Entering his fifth decade as an actor, Penn embodied an ageing classical Hollywood star with  a leery, pitch-perfect cameo in Licorice Pizza. He also has a pivotal role in Flag Day, which also stars his daughter Dylan Penn. This is his sixth film as director and the first in which he appears (along the way he has also directed music videos for Shania Twain, Peter Gabriel, Jewel and Bruce Springsteen, as well as a segment of the 2002 portmanteau film 11’09”01). Like much of his work as a filmmaker, Flag Day echoes the spirit of the cinema Penn grew up with. Here, we reflect on each of Penn’s feature films and analyse the connective tissue that links them together.

The Indian Runner (1991)

Penn’s debut is a character piece masquerading as a crime drama. Inspired by Bruce Springsteen’s song ‘Highway Patrolman’, from his 1982 album Nebraska (Penn would subsequently direct a music video for the singer’s Video Anthology / 1978-88 release), it details the relationship between two brothers who live either side of the law. David Morse’s Joe is a deputy sheriff in a small town, while Viggo Mortensen plays his Vietnam-vet sibling Frank, who is always in trouble with the law. With a supporting cast that includes Dennis Hopper, Charles Bronson and Sandy Dennis, Penn’s debut recalls the low-key dramas that dominated New Hollywood of the 1970s. Though ultimately a little too conscious of its roots, The Indian Runner is an impressive mood piece featuring an outstanding cast that also includes Valeria Golino and Patricia Arquette.

The Crossing Guard (1995)

Freddy (Jack Nicholson) and Mary Gale (Anjelica Huston) were once happily married. But since the death of their seven-year-old daughter Emily by a drunk driver (David Morse), Freddy has become consumed by grief and alcohol. Their relationship ends and Freddy barely exists as a human being. Five years later, the man who killed Emily is released from prison. Consumed with rage, and against Mary’s pleas, Freddy decides to kill him. Penn wisely avoids histrionics, opting instead to gradually ratchet up the film’s tension, until an extended chase scene that gives the climax an uneven tone. Jack Nicholson delivers a strong performance, recalling the introspective roles he played in Bob Rafelson’s 1970s films (particularly the 1972 drama The King of Marvin Gardens). If his scenes opposite Anjelica Huston lack the spark that made them such a combustible pair in Prizzi’s Honor (1985), it’s still a pleasure to see both working with meaty roles. They’re matched by Morse’s remorseful ex-con. Very much a companion piece to The Indian Runner, The Crossing Guard once again finds Penn operating as an actor’s director.

The Pledge (2001)

In many ways the final part of an unofficial trilogy, Penn’s third film once again stars Nicholson. This time he dominates throughout, with a performance that ranks alongside his turns in About Schmidt (2002) and The Departed (2006) as the finest in the later stages of his impressive career. He plays retiring Nevada detective Jerry Black, whose investigation into the death of a young girl obsesses him long after he has left office. Nicholson convincingly captures Jerry’s obsessive behaviour, which ultimately threatens to destroy him. There’s a strong supporting cast (which includes Patricia Clarkson, Benicio del Toro, Harry Dean Stanton, Aaron Eckhart, Helen Mirren, Tom Noonan, Vanessa Redgrave, Robin Wright, Mickey Rourke, Sam Shepard and an ever reliable Dale Dickey), which offers an indication of Penn’s increasing stature as a filmmaker. It’s a bleak portrait of the world, but thanks to Nicholson’s committed portrayal, Chris Menges’ rich cinematography and Penn’s restraint as a director, it marks a significant progression in his style.

Into the Wild (2007)

Penn’s most critically acclaimed and popular film is a superb adaptation of Jon Krakauer’s 1996 book. Chris McCandless was a graduate from Emory University who appeared to become disenchanted with modern life and gave it up to live within the wilds of Alaska, only to die there. Like Sebastian Junger’s The Perfect Storm, Krakauer’s book presents known facts with a hypothesis about McCandless’ final movements. Penn’s approach to character in his previous films found him perfectly suited to Krakauer’s study, while his framing, aided by Eric Gautier’s stunning cinematography, captures the beauty of the wilderness McCandless became entranced with. Treating McCandless as neither a victim nor tragic hero, Penn’s film grapples with an individual’s decision to leave the modern world behind (as such, it is the perfect companion to Werner Herzog’s stunning 2005 documentary Grizzly Man). In doing so, the film offers a portrait of the natural world that balances docudrama with a more poetic tone, echoing 19th-century painter Caspar David Friedrich’s vision of the sublime.

The Last Face (2016)

Penn’s subsequent film proved to be his most problematic. Based on a screenplay by Erin Dignam, who directed Penn and Robin Wright in the impressive 1997 drama Loved, it charts the relationship between two doctors (Charlize Theron and Javier Bardem) against the backdrop of a conflict zone in West Africa. Questions of representation dominated critical reactions to the film and Penn’s tone, usually consistent in his dramas, is uneven at best. The strong cast notwithstanding (which includes Adèle Exarchopoulos, Jean Reno and Jared Harris), the film is both a thematic outlier in Penn’s work as director – more in keeping with his real-life activities – and his least impressive.

Flag Day (2021)

Jennifer Vogel’s memoir, adapted by Fair Game writers Jez and John-Henry Butterworth, gives Penn one of his most substantial roles in years and is also a fine showcase for his daughter Dylan. (Her brother is played by real-life sibling Hopper Penn.) It tells the story of Vogel’s relationship with her father, a Mittyesque narcissist whose life comprises a series of criminal enterprises that rarely pay off. The film returns to the darker character studies that Penn excels at, but the world-weariness of the film’s tone also introduces a humour mostly absent in the actor-director’s earliest work. It’s unlikely to win over his more strident critics, but Flag Day once again highlights Penn’s wayward spirit.



Ian Haydn Smith