Sean Penn's Best Movies, Ranked
- 1Sean Penn, Tim Robbins, Kevin Bacon
Mystic River showcases Sean Penn's powerful performance in a dramatic exploration of friendship, loss, and redemption. Directed by the legendary Clint Eastwood, this film delves into the lives of three childhood friends who find themselves entangled in a heinous crime as adults. Penn's gripping portrayal of Jimmy Markum earned him an Academy Award for Best Actor, illustrating his exceptional range as an actor. With its intricate plot and outstanding ensemble cast, including Tim Robbins and Kevin Bacon, Mystic River has cemented its place as a modern classic in American cinema.
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- 2Sean Penn, Jennifer Jason Leigh, Judge Reinhold
Fast Times at Ridgemont High is a seminal coming-of-age comedy that introduced audiences to Sean Penn's comedic chops through his unforgettable portrayal of stoner Jeff Spicoli. Directed by Amy Heckerling and featuring an ensemble cast that includes Jennifer Jason Leigh, Judge Reinhold, and Phoebe Cates, this film perfectly captures the trials and tribulations faced by teenagers in suburban America during the 1980s. Although it first gained popularity as a raucous teen comedy filled with memorable one-liners, Fast Times at Ridgemont High has since been praised for its insightful examination of youth culture.
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- Al Pacino, Sean Penn, Penelope Ann Miller
Carlito's Way sees Sean Penn step into the world of gritty crime dramas with his riveting portrayal of lawyer David Kleinfeld alongside Al Pacino in Brian De Palma's stylish gangster epic. Set amidst the seedy underbelly of 1970s New York City, this thrilling saga follows ex-con Carlito Brigante (Pacino) as he attempts to escape his criminal past only to be drawn back into it by those closest to him - including Penn's duplicitous character. With its pulsing soundtrack and striking visual style, Carlito's Way remains a fan-favorite entry in both De Palma's filmography and Sean Penn's distinguished career.
- 4Susan Sarandon, Sean Penn, Robert Prosky
Sean Penn delivers a raw and poignant performance in Dead Man Walking, a gripping drama that explores the moral complexities surrounding capital punishment. Directed by Tim Robbins and co-starring Susan Sarandon as Sister Helen Prejean, the film follows the evolving relationship between a death row inmate (Penn) and the nun who becomes his spiritual advisor. Earning critical acclaim for its sensitive portrayal of a divisive issue, Penn's turn as convicted murderer Matthew Poncelet showcased his incredible depth and range as an actor, ultimately earning him an Academy Award nomination for Best Actor.
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- 5Sean Penn, Reni Santoni, Esai Morales
Bad Boys marks an early entry in Sean Penn's illustrious career, showcasing his talent in a hard-hitting drama set within the confines of a brutal juvenile detention center. Directed by Rick Rosenthal, this unflinching film follows a group of troubled teens as they navigate their way through a harsh and unforgiving environment. Penn stars as Mick O'Brien, a young offender whose impulsive actions lead to tragic consequences. With its stark portrayal of institutional violence and unforgettable performances from its young cast, Bad Boys remains a significant milestone in both Penn's acting oeuvre and the coming-of-age genre.
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- 6Sean Penn, Michelle Pfeiffer, Dakota Fanning
In I Am Sam, Sean Penn takes on the challenging role of Sam Dawson, a man with intellectual disabilities fighting for custody of his daughter Lucy (Dakota Fanning). Directed by Jessie Nelson, this emotionally charged drama delves into themes of love, family bonds, and human rights while providing Penn with one of his most complex and nuanced roles to date. His heartfelt performance garnered critical praise and an Academy Award nomination for Best Actor, further solidifying his reputation as one of Hollywood's most versatile talents.
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- 7Sean Penn, Emile Hirsch, Josh Brolin
Milk finds Sean Penn inhabiting the role of real-life gay activist Harvey Milk in Gus Van Sant's inspiring biographical film. Charting Milk's rise from humble beginnings to becoming California's first openly gay elected official at San Francisco City Hall before his tragic assassination, Penn delivers an impassioned performance that earned him his second Academy Award for Best Actor. This powerful story about courage and resilience amid adversity showcases not only Milk's tireless advocacy but also highlights Penn's remarkable ability to embody diverse characters across various genres.
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- 8Michael Douglas, Sean Penn, Deborah Kara Unger
The Game pairs Sean Penn with director David Fincher in this tense psychological thriller that sees him alongside Michael Douglas as Conrad Van Orton—the enigmatic brother who gifts him an unusual life-altering experience. Through this intricate and suspenseful tale, Penn's performance adds an element of unpredictability that serves to heighten the film's overall sense of unease. With its masterfully crafted narrative and standout performances, The Game remains a highly memorable entry within both Fincher's and Penn's filmographies.
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- 9Sean Penn, Benicio Del Toro, Naomi Watts
21 Grams pairs Sean Penn with director Alejandro González Iñárritu for a profound exploration of loss, grief, and redemption set against an unconventional non-linear narrative structure. Penn stars alongside Naomi Watts and Benicio Del Toro as Paul Rivers—a critically ill mathematician who becomes entwined in a complex web of interconnected lives following a tragic accident. With its innovative storytelling approach and emotionally resonant themes, 21 Grams stands as yet another testament to Penn's extraordinary range as an actor.
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- 10Sean Penn, Robert Duvall, Maria Conchita Alonso
Colors sees Sean Penn stepping into the world of gritty police dramas under the direction of Dennis Hopper. This strikingly realistic portrayal of gang violence in 1980s Los Angeles follows two LAPD officers (played by Penn and Robert Duvall) as they patrol the city streets in an attempt to quell the escalating conflict between rival gangs. Penn delivers a fiercely committed performance as Officer Danny "Pac-Man" McGavin, demonstrating his capacity for taking on edgy roles that challenge audience expectations.
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- 11Sean Penn, Adrien Brody, Jim Caviezel
The Thin Red Line marks Sean Penn's venture into war dramas under the visionary direction of Terrence Malick. This visually stunning adaptation of James Jones' novel explores the Battle of Guadalcanal during World War II through an ensemble cast that includes Nick Nolte, Jim Caviezel, Adrien Brody, and George Clooney. Penn's performance as 1st Sgt. Edward Welsh lends depth to the film's contemplative portrayal of soldiers grappling with their humanity amidst the horrors of war.
More The Thin Red Line- #48 of 262 onThe 200+ Best War Movies Of All Time
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- 12Sean Penn, Christopher Walken, Mary Stuart Masterson
At Close Range features Sean Penn in a gripping crime drama directed by James Foley, based on the real-life story of the notorious criminal Bruce Johnston Sr. (Christopher Walken) and his turbulent relationship with his son Brad Whitewood Jr. (Penn). Set against the backdrop of rural Pennsylvania, this film delves into themes of family, loyalty, and betrayal as Penn expertly navigates the complex emotional landscape of a young man drawn into his father's dangerous world.
- 13Michael J. Fox, Sean Penn, Don Harvey
In Casualties of War, Sean Penn delivers a compelling performance alongside Michael J. Fox in Brian De Palma's harrowing Vietnam War drama based on true events. This powerful film delves into themes of morality and camaraderie amid violence as it follows a group of American soldiers who are ultimately torn apart by a horrendous act committed during their service in Vietnam.
More Casualties of War- #168 of 262 onThe 200+ Best War Movies Of All Time
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- 14Sean Penn, Ed Harris, Gary Oldman
State of Grace finds Sean Penn immersed in New York City's Irish mob scene under Phil Joanou's direction. In this gripping crime thriller, Penn stars alongside Ed Harris and Gary Oldman as Terry Noonan – an undercover cop sent to infiltrate his childhood friends' criminal organization only to be confronted with questions about loyalty and identity.
- 15Timothy Hutton, George C. Scott, Ronny Cox
Taps marks Sean Penn's feature film debut, where he stars opposite Timothy Hutton and Tom Cruise in a gripping military drama directed by Harold Becker. Set within a prestigious military academy, this tense thriller explores themes of honor, loyalty, and rebellion as a group of cadets stages a desperate standoff against authorities attempting to shut down their school.
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- 16Timothy Hutton, Sean Penn, David Suchet
The Falcon and The Snowman showcases another facet to Sean Penn's acting range as he stars alongside Timothy Hutton in John Schlesinger's fact-based espionage drama. This captivating film charts the story of two disillusioned young Americans who sell classified information to the Soviet Union during the height of the Cold War, with Penn delivering an unforgettable performance as drug-addled ne'er-do-well Daulton Lee.
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- 17Jennifer Lopez, Sean Penn, Claire Danes
In U-Turn, Sean Penn teams up with acclaimed director Oliver Stone for an intense neo-noir crime thriller. Penn stars as Bobby, a man desperate to escape his troubled past, who becomes entangled in a vicious web of deceit and violence while stranded in a desert town.
- 18Sean Penn, Frances McDormand, David Byrne
This Must Be The Place sees Sean Penn transform into an aging rock star named Cheyenne in Paolo Sorrentino's quirky drama about self-discovery and redemption. Featuring memorable visuals and a mesmerizing performance from Penn, this unconventional tale takes viewers on an emotional journey across America as Cheyenne searches for his estranged father's Nazi tormentor.
- 19Sean Penn, Samantha Morton, Uma Thurman
Sweet and Lowdown pairs Sean Penn with writer-director Woody Allen for a delightful comedy-drama that pays homage to jazz music of the 1930s. In this faux-biographical tale, Penn stars as eccentric guitarist Emmet Ray whose talent is only matched by his wild ego, earning him an Academy Award nomination for Best Actor.
- 20Sean Penn, Elizabeth McGovern, Nicolas Cage
Racing with The Moon displays Sean Penn's more tender side in Richard Benjamin's coming-of-age romance set during World War II. Co-starring Elizabeth McGovern and Nicolas Cage, this nostalgic film follows two young friends (Penn and Cage) as they navigate love and loss before being shipped off to combat overseas.
- 21Catherine McCormack, Sarah Polley, Sean Penn
The Weight of Water sees Sean Penn delve into the psychological thriller genre under the direction of Kathryn Bigelow. This atmospheric film weaves together two parallel narratives set over a century apart, with Penn starring as Thomas Janes—a modern-day poet whose personal life unravels during a sailing trip meant to investigate an unsolved murder from the 19th century.
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- Josh Brolin, Ryan Gosling, Nick Nolte
Gangster Squad brings Sean Penn into the world of organized crime under Ruben Fleischer's direction. In this stylish action thriller set in 1940s Los Angeles, Penn stars as notorious mob boss Mickey Cohen alongside Josh Brolin and Ryan Gosling as LAPD officers trying to bring down his criminal empire. With its visually striking set pieces and Penn's menacing portrayal of Cohen, Gangster Squad offers a thrilling glimpse into Hollywood's darker history.
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- 23Nicole Kidman, Sean Penn, Catherine Keener
The Interpreter finds Sean Penn alongside Nicole Kidman in Sydney Pollack's taut political thriller set within the high-stakes world of international diplomacy. As federal agent Tobin Keller, Penn delivers an emotionally charged performance while unraveling an assassination plot threatening global stability.
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- 24Sean Penn, Jude Law, Kate Winslet
All The King's Men features Sean Penn taking on the larger-than-life role of Southern politician Willie Stark in Steven Zaillian's adaptation of Robert Penn Warren’s Pulitzer Prize-winning novel. A tale of ambition and corruption set against the backdrop of American politics, this compelling drama highlights both the dark side of power and the captivating nature of persuasive leaders.
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- 25Brad Pitt, Sean Penn, Jessica Chastain
The Tree Of Life pairs Sean Penn with director Terrence Malick once again for an ambitious existential drama starring Brad Pitt and Jessica Chastain. This visually poetic film delves into profound questions about life, death, and the nature of existence as it follows a man (Penn) reflecting on his childhood in 1950s Texas. The Tree Of Life's experimental narrative structure and captivating visuals make it a truly unique cinematic experience.
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- 26Javier Bardem, Olivier Martinez, Andrea Di Stefano
Before Night Falls showcases Sean Penn's chameleonic abilities with a brief but impactful appearance in Julian Schnabel's biographical drama about Cuban writer and dissident Reinaldo Arenas (Javier Bardem). This visually sumptuous film explores themes of political oppression, artistry, and homosexuality while featuring an ensemble cast that includes Johnny Depp and Olivier Martinez.
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- 27Kristin Scott Thomas, Sean Penn, Anne Bancroft
Up at the Villa sees Sean Penn take on the role of expatriate Rowley Flint in Philip Haas' adaptation of W. Somerset Maugham’s novella set against pre-World War II Tuscany. Starring Kristin Scott Thomas as widow Mary Panton, this romantic drama explores themes of love, desperation, and intrigue amidst breathtaking Italian landscapes.
- 28Naomi Watts, Sean Penn, Sam Shepard
Fair Game pairs Sean Penn with Naomi Watts in Doug Liman's dramatic retelling of real-life events surrounding CIA operative Valerie Plame (Watts) and her husband Joseph Wilson (Penn). This gripping political thriller sheds light on government conspiracy and personal sacrifice while offering riveting performances from both Penn and Watts.
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- 29Robert De Niro, Sean Penn, Demi Moore
We're No Angels showcases Sean Penn's comedic prowess as he teams up with Robert De Niro in Neil Jordan's entertaining caper about two escaped convicts posing as priests on Christmas Eve. This hilarious comedy explores themes of mistaken identity and redemption while allowing audiences to witness Penn's versatility beyond hard-edged roles.
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- 30Donald Sutherland, Jack Warden, Sean Penn
Crackers finds Sean Penn in Louis Malle's light-hearted caper comedy alongside Donald Sutherland and Jack Warden. This entertaining heist film features Penn as Dillard, part of a motley crew of amateur thieves attempting to rob a pawnshop in San Francisco's Mission District.
- 31Robert De Niro, Robin Williams, Sean Penn
Dear America: Letters Home from Vietnam is an emotional documentary featuring Sean Penn as one of the many celebrity narrators who give voice to actual letters written by American soldiers during the Vietnam War. Directed by Bill Couturié, this heartrending film offers a poignant and deeply humanizing insight into the lives of those affected by war.
- 32Sean Penn, Martin Sheen, Sam Wanamaker
Judgment in Berlin features Sean Penn in an intense courtroom drama directed by Leo Penn, his father. Set amidst the backdrop of the Cold War, this thought-provoking film narrates the true story of an East German family who hijack a Polish airplane to escape to West Berlin and face trial for their actions. Penn's engaging performance as defense attorney Mark Lane adds depth to the film's exploration of political tensions, justice, and human rights.
- 33Sean Penn, Kevin Spacey, Chazz Palminteri
Hurlyburly showcases Sean Penn's intense acting skills alongside Kevin Spacey, Robin Wright, and Chazz Palminteri in Anthony Drazan's searing drama about disillusioned Hollywood insiders seeking solace amid fast-paced excesses. Adapted from David Rabe's acclaimed stage play, this razor-sharp film captures Penn's fiery performance as the deeply troubled Eddie.
- 34Sean Penn, Robin Wright, John Travolta
She's So Lovely reunites Sean Penn with director Nick Cassavetes for an offbeat romantic drama co-starring Robin Wright and John Travolta. In this enthralling tale of love, obsession, and redemption, Penn delivers a nuanced performance as Eddie Quinn - a man struggling to reconcile his past with his future.
- 35Sean Penn, Don Cheadle, Jack Thompson
The Assassination of Richard Nixon finds Sean Penn in a riveting role as Samuel Bicke, a desperate man who plots to kill President Nixon in Niels Mueller's gripping character study. Based on real-life events, this darkly captivating film offers an intriguing exploration of the human psyche pushed to its limits.
- 36Kristen Stewart, Bruce Willis, Robert De Niro
What Just Happened features Sean Penn in Barry Levinson's satirical comedy about the trials and tribulations of Hollywood filmmaking alongside Robert De Niro and Bruce Willis. Aided by sharp wit and engaging performances from its ensemble cast, this film offers a biting insider's look at the entertainment industry.
- Mel Gibson, Sean Penn, Natalie Dormer
The Professor and The Madman sees Sean Penn team up with Mel Gibson for Farhad Safinia’s fascinating biographical drama about the creation of the Oxford English Dictionary. In this engrossing tale of language and obsession, Penn stars as Dr. William Chester Minor – an American Army surgeon whose contributions to the dictionary are made all the more remarkable considering he was committed to a mental institution during his work.
- 38Chiara Mastroianni, Catherine Deneuve, Danielle Darrieux
Persepolis grants audiences a unique opportunity to experience Sean Penn lending his voice talents to Marjane Satrapi’s critically acclaimed animated adaptation of her graphic novels about growing up in Iran during the Islamic Revolution. Alongside Catherine Deneuve and Gena Rowlands, Penn's compelling voice work serves to further enrich the film's evocative storytelling and striking visuals.
- 39Jodie Foster, Steven Spielberg, Rob Cohen
The Cutting Edge: The Magic of Movie Editing is a fascinating documentary that features Sean Penn as a narrator, offering valuable insights into the often-overlooked art of film editing. Directed by Wendy Apple, this informative documentary delves into the creative process behind some of cinema's most memorable moments and showcases numerous interviews with iconic editors and filmmakers.
- 40Sean Penn, Joan Baez, Christopher Hitchens
Phil Ochs: There but for Fortune sees Sean Penn contributing his talents as an interviewee in Kenneth Bowser’s gripping documentary about the influential yet troubled folk singer-songwriter Phil Ochs. This insightful film offers a compelling exploration of Ochs' life, music, and activism during the turbulent 1960s.
- 41Sean Penn, Woody Harrelson, Hank Azaria
Cool Blue features a young Sean Penn in Mark Mullin's offbeat romantic comedy about an aspiring artist (Woody Harrelson) whose life becomes entwined with an enigmatic woman named Dusty (Hank Azaria). Although only appearing briefly in this indie gem, Penn's presence highlights his early commitment to exploring diverse roles and genres throughout his career.
- 42Sean Penn, Madonna, Paul Freeman
Shanghai Surprise marks one of Sean Penn's more notorious roles alongside then-wife Madonna in Jim Goddard’s quirky adventure-comedy set during 1930s China. Although not well-received upon its release, this entertaining romp provides fans with an intriguing look at Penn’s early forays into comedic performances.
- 43
Heart Stopper
Morgan Freeman, Sean Penn, Heather GrahamHeart Stopper is a lesser-known thriller featuring Sean Penn as a concerned doctor who discovers an experimental heart operation could be life-threatening for his patient (Jennifer Jason Leigh). Directed by Peter Keglevic, this suspenseful drama highlights Penn's ability to elevate any role with his unwavering commitment to character development.
- 44
This So-Called Disaster
Woody Harrelson, Cheech Marin, Nick NolteThis So-Called Disaster sees Sean Penn collaborating with director Michael Almereyda for an intriguing behind-the-scenes look at Sam Shepard's play The Late Henry Moss. As both actor and co-producer for the play, Penn provides valuable insights into the creative process that goes into bringing such an emotionally charged production to life.
- 45
Love
Sean Penn, Robin Wright, William HurtLove is a unique sci-fi drama directed by William Eubank that features Sean Penn in a voice-only cameo role. Set aboard the International Space Station, this visually striking film explores themes of isolation and human connection as astronaut Lee Miller (Gunner Wright) grapples with his solitude during an extended mission.
- 46Joaquin Phoenix, Claire Danes, Sean Penn
It's All About Love stars Sean Penn alongside Joaquin Phoenix and Claire Danes in Thomas Vinterberg’s surreal romantic drama set in a near-future dystopia. As Marciello, Penn delivers a captivating performance that adds to the enigmatic atmosphere of this unconventional love story.
- 47
Buy the Ticket, Take the Ride
Bill Murray, Nick Nolte, Gary BuseyBuy the Ticket, Take the Ride features Sean Penn's insightful commentary in Tom Thurman’s engaging documentary about legendary journalist Hunter S. Thompson. With a host of celebrity interviews and archival footage, this film pays tribute to Thompson's iconoclastic spirit while exploring his influence on American journalism and popular culture.
Bukowski: Born into This finds Sean Penn among many celebrities offering insight into the life and work of infamous writer Charles Bukowski in John Dullaghan's revelatory documentary. Through archival footage and intimate interviews, viewers are given a rare glimpse into the mind of one of America's most complex literary figures.
- 49
Deflating the Elephant
Sean PennDeflating the Elephant is a thought-provoking documentary narrated by Sean Penn that dissects conservative language strategies used in American politics. Based on George Lakoff's influential book Don't Think of an Elephant, this eye-opening film delves deep into how words can shape public opinion.
- 50
War Made Easy: How Presidents & Pundits Keep Spinning Us to Death
Sean PennWar Made Easy: How Presidents & Pundits Keep Spinning Us to Death is a provocative documentary narrated by Sean Penn that examines how government officials and media pundits manipulate information to garner public support for war efforts. Through historical footage and expert interviews, this enlightening film exposes the mechanisms behind political spin and its consequences.
- 51Ben Affleck, Matt Damon, Marisa TomeiThe People Speak is a documentary tv program/film.
- 52
A Constant Forge
Peter FalkA Constant Forge is a 2000 documentary film directed by Charles Kiselyak about the life and work of John Cassavetes. It contains interviews with Cassavetes himself as well as recollections by actors who have worked with him and thoughts by admirers, including Lynn Carlin, Seymour Cassel, Peter Falk, John A. Gallagher, Ben Gazzara, Lelia Goldoni, Annette Insdorf, Carol Kane, Sean Penn, Gena Rowlands and Jon Voight. - Alana Haim, Cooper Hoffman, Sean PennAlana Kane and Gary Valentine grow up, run around and fall in love in California's San Fernando Valley in the 1970s.
- 54Robert Downey Jr., Alyssa Milano, Sean PennHugo Pool is a 1997 American romantic comedy film, directed by Robert Downey, Sr., starring Alyssa Milano and Patrick Dempsey.
- 55Britney Spears, Paris Hilton, Pamela AndersonThis film is an American comedy/mockumentary motion picture released in 2003 starring actor and comedian Pauly Shore. The cameo-filled movie begins as a semi-autobiographical retelling of Shore's early success and dwindling popularity in the late 1990s. The film, with the original working title of You'll Never Wiez in This Town Again, marked Shore's debut as a writer, director, and producer.
- 56
See How They Run
Sean Penn, Bill Maher, Jesse Jackson - Sean Penn, Tye Sheridan, Gbenga AkinnagbeA young paramedic gets a crash course in lifesaving techniques while working with a grizzled New York City veteran.More Asphalt City
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- Dylan Penn, Sean Penn, Josh BrolinJennifer Vogel's father, John, is larger than life. As a child, she marvels at his magnetizing energy and ability to make everything feel like a grand adventure. John teaches her so much about love and joy, but he also happens to be the most notorious counterfeiter in U.S. history. Jennifer now struggles to rise above the wreckage of the past while reconciling the inescapable bond between a daughter and her father.More Flag Day
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