7 Sean Penn Movies to Watch if You Loved Him in 'One Battle After Another'

Sean Penn delivers a performance that stays with viewers in Paul Thomas Anderson's One Battle After Another. He embodies the role of Colonel Stephen J. Lockjaw, a corrupt military official whose presence looms over the story. The movie follows ex-revolutionaries who reunite after sixteen years when their deadly enemy resurfaces. They must rescue one of their own daughters from this threatening figure. Penn brings depth to characters who represent institutional power gone wrong.

His performance in this action thriller displays why he remains one of the cinema's most engaging actors. With two Academy Awards already in his collection, Penn continues to take on challenging roles. His career spans years and includes performances that range from character-driven narratives to intense drama. For those captivated by his turn in Anderson's recent work, exploring his filmography reveals a pattern of bold choices.

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Milk, 21 Grams, The Assassination of Richard Nixon, and four other Sean Penn movies to watch if you liked him in One Battle After Another

1) Mystic River (2003)

A still from the movie (Image via Apple TV)

Sean Penn received his first Oscar for this devastating drama directed by Clint Eastwood. He portrays Jimmy Markum, a father whose daughter is killed. The performance cuts deep without ever feeling too much.

Penn displays a man unravelling as grief takes control of his life. The movie explores how childhood trauma echoes through time. Three friends reunite under challenging circumstances in their Boston neighborhood.

Each holds scars from an event that happened when they were young. Penn's work here displays his potential to display raw pain. His sequences hold weight because he never asks for sympathy. The character makes questionable choices driven by rage and loss. The role displays Penn's commitment to emotional truth.

The movie is available on Amazon Prime for viewers to watch.

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2)Dead Man Walking (1995)

A still from the movie (Image via Apple TV)

This prison drama earned Sean Penn his first Oscar nomination for Best Actor. He displays Matthew Poncelet, a death row inmate seeking spiritual counsel. The role required Penn to create sympathy for a character who committed horrible crimes.

He displays humanity by portraying someone facing execution. Sister Helen Prejean, portrayed by Susan Sarandon, frequently visits him. Their conversations form the heart of this story about forgiveness and redemption. Penn never softens the character's excuses or past actions.

Instead, he presents a complete person capable of remorse and growth. The movie examines capital punishment without taking a preachy stance. Penn's performance walks a difficult line between accountability and vulnerability.

The movie is available on Amazon Prime for viewers to watch.

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3) Milk (2008)

A still from the movie (Image via Apple TV)

Sean Penn won his second Academy Award for portraying Harvey Milk in this biographical drama. Milk was California's first openly gay elected official and a pioneering activist. The movie chronicles his political career and fight for LGBTQ rights. Penn disappears into the role of conviction and warmth.

He captures Milk's determination and charisma without resorting to imitation. The story takes place in San Francisco during the 1970s. Milke encounters opposition from both conservative groups and politicians.

Penn displays the personal cost of fighting for change and living authentically. His acting balances public power with private moments of doubt. Director Gus Van Sant creates an intimate portrait of a historical figure. Penn's work honors Milk's legacy while creating a fully realized character.

The movie is available on Amazon Prime for viewers to watch.

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4) 21 Grams (2003)

A still from the movie (Image via Apple TV)

This unconventional drama reunites Sean Penn with director Alejandro González Iñárritu. He embodies the role of Paul Rivers, a mathematics professor with a failing heart. The movie weaves three characters together through tragedy and its aftermath.

Penn's acting is quiet and measured compared to his other work. He portrays a man confronting mortality while seeking meaning. The narrative structure jumps through time, revealing connections slowly.

Benicio del Toro and Naomi Watts complete the whole trio. Every character deals with guilt and loss in separate ways. Penn brings restriction to a role that could easily turn melodramatic. His sequences with Watts carry genuine emotional weight. Penn's work here demonstrates his potential to make a significant contribution to the narrative.

21 Grams is available on Amazon Prime for viewers to watch.

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5) I Am Sam (2001)

A still from the movie (Image via Apple TV)

Sean Penn received an Oscar nomination for this drama about disability and fatherhood. He embodies the role of Sam Dawson, a man with a developmental disability who raises his daughter alone. The role sparked debate about acting choices and representation. Penn approached the character with preparation and sincerity. He spent time with people in the disability community before shooting.

The premise follows Sam's fight to keep the custody of his young daughter, Lucy. A lawyer, portrayed by Michelle Pfeiffer, takes his case and learns from him. The movie explores society's assumptions about love and human potential. Penn's performance never condescends to the audience or the character. The film raises questions about what makes someone a good parent. Penn brings dignity to a character who encounters constant underestimation.

I Am Sam is available on Amazon Prime for viewers to watch.

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6) Carlito's Way (1993)

A still from the movie (Image via Apple TV)

This crime drama, directed by Brian De Palma, features Sean Penn in a memorable supporting role. He embodies the role of David Kleinfelf, a lawyer who becomes entangled in criminal actions. Penn transformed himself with physical choices that define the character.

The movie follows Carlito Brigante, portrayed by Al Pacino, as he attempts to leave his past behind. Kleinfeld's desperation and addiction pull Carlito back into danger. Penn creates a character who is both threatening and pathetic. His sequences crackle with unpredictable, poor decisions and energy.

The performance showcases Penn's ability to fully embody unlikable characters. De Palma crafts a stylish thriller about consequences and loyalty. Penn makes Kleinfeld unforgettable despite limited screen time.

Carlito's Way is available on Netflix for viewers to watch.

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7) The Assassination of Richard Nixon (2004)

A still from the movie (Image via Apple TV)

Sean Penn features in this character study drama based on a true story. He portrays Samuel Bicke, a man whose life gradually falls apart. Bicke eventually attempts to hijack a plane in 1974. The movie examines American disillusionment and mental deterioration.

Sean Penn creates a portrait of misplaced anger and loneliness. The character records audio tapes explaining his grievances and worldview. Sean Penn delivers these monologues with a revealing candor that avoids seeking pity.

The movie is available on Amazon Prime for viewers to watch.

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Sean Penn's career displays a consistent pursuit of complex characters and challenging material. His filmography rewards exploration beyond his most recognized roles. Every performance reveals separate aspects of his considerable range and devotion to craft.

Edited by Mannjari Gupta