The 10 Most Underrated Sean Penn Movies, Ranked (from least to most underrated)

Sean Penn has moved between intimate character pieces and large scale thrillers while collecting major industry honors along the way. He earned two Academy Awards for Best Actor for roles in ‘Mystic River’ and ‘Milk’ and has worked with filmmakers across several generations, from Brian De Palma and Sydney Pollack to Doug Liman and Oliver Stone. His filmography spans early ensemble work, breakthrough dramas, political stories, and genre experiments that show how much range he brings to the screen.

This countdown looks at ten projects that did not always command the biggest spotlight yet offer clear snapshots of the roles and productions that shaped his career. The selections cover studio releases and independent efforts, adaptations from novels and journalism, and collaborations with actors who went on to headline their own eras.

‘The Gunman’ (2015)

This action thriller was directed by Pierre Morel and adapted from Jean Patrick Manchette’s novel ‘The Prone Gunman’. The international cast includes Javier Bardem, Idris Elba, Ray Winstone, and Mark Rylance, with production that moved through locations in Spain, the United Kingdom, and Africa. The film follows a former private security operative who is targeted after a past assignment comes back into view.

Penn plays Jim Terrier, a onetime contractor whose attempt to build a quieter life is disrupted by a coordinated pursuit. The story threads through non governmental work, resource concessions, and cross border travel while the character tracks who ordered the hit and why it connects to an earlier mission.

‘She’s So Lovely’ (1997)

Directed by Nick Cassavetes from an original screenplay by John Cassavetes, this drama pairs Penn with Robin Wright and John Travolta. The film premiered at the Cannes Film Festival where Penn received the Best Actor award. The project drew attention for bringing a late script by John Cassavetes to the screen with a cast that includes James Gandolfini, Harry Dean Stanton, and Debi Mazar.

Penn portrays Eddie Quinn, whose life splinters after a breakdown and separation from his wife Maureen. Years later he returns to find Maureen remarried to Joey and raising a child, which sets off custody questions and confrontations that test the limits of past loyalty and present responsibility.

‘All the King’s Men’ (2006)

Written and directed by Steven Zaillian, this adaptation of Robert Penn Warren’s novel focuses on the political ascent of a Southern governor. The ensemble features Jude Law, Kate Winslet, Anthony Hopkins, Patricia Clarkson, James Gandolfini, and Mark Ruffalo. Production took place largely in Louisiana with period detail across government offices, rallies, and pressrooms.

Penn plays Willie Stark, a populist leader whose rise brings investigations, shifting alliances, and choices that entangle his staff and a reporter named Jack Burden. The film traces legislative battles, patronage networks, and the way public works projects intersect with private influence.

‘The Interpreter’ (2005)

Sydney Pollack directed this political thriller starring Nicole Kidman and Penn. The production received rare permission to film inside United Nations Headquarters, which allowed scenes in the General Assembly and other secure areas. The cast also includes Catherine Keener and Jesper Christensen with sequences staged across New York City.

Penn appears as Secret Service agent Tobin Keller, who is assigned to protect a visiting head of state after an interpreter overhears a death threat in a rare dialect. The investigation follows security protocols, diplomatic immunity questions, and the risks of operating inside an international institution while the agent evaluates whether the witness is in danger or withholding information.

‘Fair Game’ (2010)

Doug Liman’s drama adapts two books connected to the Valerie Plame case, drawing from the memoir by Valerie Plame and a volume by Joseph C Wilson. Naomi Watts stars as Plame with Penn as Wilson, and the film reconstructs events that played out across Washington and the intelligence community. The project screened at Cannes and later reached wider release.

Penn’s role charts Wilson’s trip to Niger, his subsequent newspaper column, and the fallout that followed the exposure of his wife’s covert status. The narrative includes the front company Brewster Jennings and Associates, congressional testimony, and the legal process that examined how classified information moved from offices to the press.

‘U Turn’ (1997)

Oliver Stone directed this neo noir based on John Ridley’s novel ‘Stray Dogs’. The film was shot in Arizona, with Superior providing the sun baked streets and storefronts seen throughout. The ensemble includes Jennifer Lopez, Nick Nolte, Joaquin Phoenix, Claire Danes, Billy Bob Thornton, and Jon Voight, each tied to the town’s layered schemes.

Penn plays Bobby Cooper, a drifter who stops for a car repair and becomes enmeshed in a murder for hire plot. The story stacks double crosses, unpaid debts, and small town rivalries as the character tries to secure cash and an exit while the town’s history keeps pulling him back in.

‘At Close Range’ (1986)

James Foley directed this crime drama inspired by the real life Johnston family gang in rural Pennsylvania. The cast features Christopher Walken, Mary Stuart Masterson, Crispin Glover, Kiefer Sutherland, and Tracey Walter. The production leaned on farm roads, small town shops, and field locations to mirror the setting of the original cases.

Penn stars as Brad Whitewood Jr, a teenager who reconnects with his estranged father and is drawn into a burglary ring. The plot follows recruiting tactics, witness intimidation, and the legal steps that follow a series of robberies as members of the crew face fracture and retaliation.

‘Casualties of War’ (1989)

Brian De Palma directed this war drama derived from Daniel Lang’s reporting in The New Yorker that became a book under the same name. The film shot largely in Thailand and uses jungle terrain and village sets to depict operations during the Vietnam War. Michael J Fox, Don Harvey, John C Reilly, and John Leguizamo round out the platoon.

Penn appears as Sergeant Tony Meserve, the squad leader at the center of a criminal act and the events that follow. The story traces chain of command, testimony from soldiers, and court martial proceedings while contrasting orders in the field with the systems that evaluate conduct after a mission.

‘State of Grace’ (1990)

Phil Joanou’s New York crime story stars Penn alongside Gary Oldman, Ed Harris, and Robin Wright. Filming took place in Hell’s Kitchen and other city locations, with scenes that use bars, tenements, and festival streets to frame the neighborhood. The film arrived the same year as other high profile organized crime releases and features a script by Dennis McIntyre.

Penn plays Terry Noonan, an undercover police officer who returns to his old block and reconnects with a friend inside an Irish American crew. The narrative follows surveillance, internal disputes over protection rackets, and the pressure that builds as loyalties within the gang collide with the demands of an ongoing investigation.

‘Carlito’s Way’ (1993)

Directed by Brian De Palma and adapted from Edwin Torres’s novels ‘After Hours’ and ‘Carlito’s Way’, this crime drama stars Al Pacino with Penn in a key supporting role. The cast includes Penelope Ann Miller, John Leguizamo, and Viggo Mortensen, with New York locations that move from nightclubs to courtrooms to train platforms.

Penn plays attorney David Kleinfeld, whose actions pull Pacino’s character back toward the life he is trying to leave. The film maps legal strategy, parole conditions, and organized crime rivalries while building to sequences in a nightclub and at Grand Central that converge past decisions with present danger.

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