Sean Penn Trailers
Red Rue Express TrailerSamuel Bayer Beyond the Frame TrailerLearning, Studying… Always Perfecting: The Making of One Battle After Another Trailer
Sean Justin Penn (born August 17, 1960) is an American actor and film director. He has won two Academy Awards, for his roles in the mystery drama Mystic River (2003) and the biopic Milk (2008).
Penn began his acting career in television, with a brief appearance in episode 112 of Little House on the Prairie on December 4, 1974, directed by his father Leo Penn. Following his film debut in the drama Taps (1981), and a diverse range of film roles in the 1980s, including Fast Times at Ridgemont High (1982) and Bad Boys (1983), Penn garnered critical attention for his roles in the crime dramas At Close Range (1986), State of Grace (1990), and Carlito's Way (1993). He became known as a prominent leading actor with the drama Dead Man Walking (1995), for which he earned his first Academy Award nomination and the Silver Bear for Best Actor at the Berlin Film Festival. Penn received another two Oscar nominations for Woody Allen's comedy-drama Sweet and Lowdown (1999) and the drama I Am Sam (2001), before winning his first Academy Award for Best Actor in 2003 for Mystic River and a second one in 2008 for Milk. He has also won a Best Actor Award at the Cannes Film Festival for the Nick Cassavetes-directed She's So Lovely (1997), and two Volpi Cups for Best Actor at the Venice Film Festival for the indie film Hurlyburly (1998) and the drama 21 Grams (2003).
Penn made his feature film directorial debut with The Indian Runner (1991), followed by the drama film The Crossing Guard (1995) and the mystery film The Pledge (2001); all three were critically well received. Penn directed one of the 11 segments of 11'09"01 September 11 (2002), a compilation film made in response to the September 11 attacks. His fourth feature film, the biographical drama survival movie Into the Wild (2007), garnered critical acclaim and two Academy Award nominations.
In addition to his film work, Penn has engaged in political and social activism, including his criticism of the George W. Bush administration, his contact with the Presidents of Cuba and Venezuela, and his humanitarian work in the aftermath of Hurricane Katrina in 2005 and the 2010 Haiti earthquake.
Most Popular Sean Penn Trailers
Total trailers found: 124
23 September 2025
Washed-up revolutionary Bob exists in a state of stoned paranoia, surviving off-grid with his spirited, self-reliant daughter, Willa.
07 September 2008
Executive Producer Sean Penn presents "Witch Hunt," a gripping indictment of the American justice system told through the lens of one small town.
01 September 2002
Rosy-Fingered Dawn is a film on Terrence Malick. It is about the making of BADLANDS, DAYS OF HEAVEN, THE THIN RED LINE and the personal involvement of some of the most representative figures of the American culture itself.
11 May 2016
An island populated entirely by happy, flightless birds or almost entirely. In this paradise, Red, a bird with a temper problem, speedy Chuck, and the volatile Bomb have always been outsiders.
12 September 1997
In honor of his birthday, San Francisco banker Nicholas Van Orton, a financial genius and a cold-hearted loner, receives an unusual present from his younger brother, Conrad: a gift certificate to play a unique kind of game.
18 December 2013
A timid magazine photo manager who lives life vicariously through daydreams embarks on a true-life adventure when a negative goes missing.
21 September 2007
After graduating from Emory University in 1992, top student and athlete Christopher McCandless abandons his possessions, gives his entire $24,000 savings account to charity, and hitchhikes to Alaska to live in the wilderness.
08 October 2003
The lives of three men who were childhood friends are shattered when one of them suffers a family tragedy.
26 November 2021
The story of Gary Valentine and Alana Kane growing up, running around and going through the treacherous navigation of first love in the San Fernando Valley, 1973.
10 November 1993
Free after years in prison, Carlito Brigante intends to give up his criminal ways, but it's not long before the ex-con is sucked back into the New York City underworld.
29 October 1999
One day at work, unsuccessful puppeteer Craig finds a portal into the head of actor John Malkovich. The portal soon becomes a passion for anybody who enters its mad and controlling world of overtaking another human body.
23 December 1998
The story of a group of men, an Army Rifle company called C-for-Charlie, who change, suffer, and ultimately make essential discoveries about themselves during the fierce World War II battle of Guadalcanal.
17 May 2011
The impressionistic story of a Texas family in the 1950s. The film follows the life journey of the eldest son, Jack, through the innocence of childhood to his disillusioned adult years as he tries to reconcile a complicated relationship with his father.
09 January 2013
Los Angeles, 1949. Ruthless, Brooklyn-born mob king Mickey Cohen runs the show in this town, reaping the ill-gotten gains from the drugs, the guns, the prostitutes and — if he has his way — every wire bet placed west of Chicago.
18 November 2003
Paul Rivers, an ailing mathematician lovelessly married to an English émigré; Christina Peck, an upper-middle-class suburban housewife and mother of two girls; and Jack Jordan, a born-again ex-con, are brought together by a terrible accident that changes their lives.
05 August 1983
Meet Joel Goodson, an industrious, college-bound 17-year-old and a responsible, trustworthy son. However, when his parents go away and leave him home alone in the wealthy Chicago suburbs with the Porsche at his disposal he quickly decides he has been good for too long and it is time to enjoy himself.
28 December 2001
Sam, a neurodivergent man, has a daughter with a homeless woman who abandons them when they leave the hospital, leaving Sam to raise Lucy on his own.
16 October 2009
Max imagines running away from his mom and sailing to a far-off land where large talking beasts—Ira, Carol, Douglas, the Bull, Judith and Alexander—crown him as their king, play rumpus, build forts and discover secret hideaways.
05 November 2008
The true story of Harvey Milk, the first openly gay man ever elected to public office. In San Francisco in the late 1970s, Harvey Milk becomes an activist for gay rights and inspires others to join him in his fight for equal rights that should be available to all Americans.
23 August 2003
Following the career of Björk, this documentary looks at her early musical career with local icelandic bands, her acclaimed stint in The Sugarcubes, and her massive success as a free-spirited solo artist.
25 March 1983
Mick O'Brien is a young Chicago street thug torn between a life of petty crime and the love of his girlfriend.
13 August 1982
A group of Southern-California high school students ignore their studies in favor of indulging in their teenage distractions.
08 April 2005
After Silvia Broome, an interpreter at United Nations headquarters, overhears plans of an assassination, an American Secret Service agent is sent to investigate.
20 May 2010
A devoted wife and mother leads a secret life as a CIA agent until her husband’s article exposes a scandal, putting her identity and loved ones at risk.
19 January 2001
A police chief, about to retire, pledges to help a woman find her daughter's killer.
14 September 1990
Hell's Kitchen, New York. Terry Noonan returns home after a ten-year absence. He soon reconnects with Jackie, a childhood friend and member of the Irish mob, and rekindles his love affair with Jackie's sister Kathleen.
15 April 1988
A confident young cop is shown the ropes by a veteran partner in the dangerous gang-controlled barrios of Los Angeles, where the gang culture is enforced by the colors the members wear.
17 September 2020
A virtual table read of the classic 1982 hit Fast Times at Ridgemont High. The all-star cast includes Jennifer Aniston, Dane Cook, Morgan Freeman, Jimmy Kimmel, Shia LaBeouf, John Legend, Ray Liotta, CORE co-founder Sean Penn, Brad Pitt and Julia Roberts.
24 August 2011
A bored, retired rock star living in Ireland sets out to find his dead father's tormentor, an ex-Nazi war criminal who is a refugee in the U.
29 December 1995
A death row inmate turns for spiritual guidance to a local nun in the days leading up to his scheduled execution for the murders of a young couple.
18 August 1989
During the Vietnam War, a soldier finds himself the outsider of his own squad when they unnecessarily kidnap a female villager.
12 May 2023
A young paramedic is paired with a seasoned partner on the night shift in New York revealing a city in crisis.
03 December 1999
In the 1930s, jazz guitarist Emmet Ray idolizes Django Reinhardt, faces gangsters and falls in love with a mute woman.
10 September 2010
I'm Still Here is a portrayal of a tumultuous year in the life of actor Joaquin Phoenix. With remarkable access, the film follows the Oscar-nominee as he announces his retirement from a successful film career in the fall of 2008 and sets off to reinvent himself as a hip-hop musician.
03 October 1997
When a desperate man’s car breaks down in a bizarre desert town while evading vengeful bookies, he becomes entangled in a dangerous love triangle.
20 December 1981
Military cadets take extreme measures to ensure the future of their academy when its existence is threatened by local condo developers.
11 January 2017
Miguel, a heroic Spanish doctor, puts himself in harm's way to deliver medical treatment to the victims of military uprisings in Africa.
27 June 2024
A woman taking a cab ride from JFK airport engages in a conversation with the driver about the important relationships in their lives.
12 March 2021
As a teenager in the '90s, Soleil Moon Frye carried a video camera everywhere she went. She documented hundreds of hours of footage and then locked it away for over 20 years.
26 January 1995
Unable to move on from the loss of his daughter, Freddy, now a shell of the person he was before, swears to kill the man responsible for her death.
17 October 2008
During the course of an ordinary week in Hollywood, movie producer Ben must navigate his way through shark-infested waters as he struggles to complete his latest projects.
31 October 1997
After a man is accused of driving his third wife to suicide, his first wife Hedda, a troubled woman who can't hate or hurt others even if they had wronged her, is subpoenaed to testify on his abusive behavior during their marriage.
18 April 1986
Brad Whitewood Jr. lives in rural Pennsylvania and has few prospects. Against his mother's wishes, he seeks out his estranged father, the head of a gang of thieves in a nearby town.
07 March 2019
Professor James Murray begins work compiling words for the first edition of the Oxford English Dictionary in the mid 19th century, and receives over 10,000 entries from a patient at Broadmoor Criminal Lunatic Asylum, Dr.
20 August 2021
A father lives a double life as a counterfeiter, bank robber and con man in order to provide for his daughter.
13 December 2009
A look at America's struggles with war, class, race and women's rights. based on Howard Zinn's "A People's History of the United States.
07 November 2024
During the 1972 Munich Olympics, an American sports broadcasting crew finds itself thrust into covering the hostage crisis involving Israeli athletes.
30 March 2001
A newspaper photographer researches an 1873 double homicide and finds her own life paralleling that of a witness who survived the tragic ordeal.
02 June 1989
Two escaped cons' only prayer to escape is to pass themselves off as priests and pass by the police blockade at the border into the safety of Canada.
23 July 2021
For over 40 years Val Kilmer, one of Hollywood's most mercurial and/or misunderstood actors, has been documenting his own life and craft through film and video.
10 September 2006
The story of an idealist's rise to power in the world of Louisiana politics and the corruption that leads to his ultimate downfall.
09 February 2014
In celebration of the 50th anniversary of The Beatles' first appearance on The Ed Sullivan Show, this magnificent star-studded tribute salutes the Fab Four.
16 February 2015
Eight years after fleeing the Congo following his assassination of that country's minister of mining, former assassin Jim Terrier is back, suffering from PTSD and digging wells to atone for his violent past.
23 March 1984
In a small coastal California town, Henry and Nicky are pals from blue collar families with only a short time before they ship off to World War II.
03 September 2000
Spanning several decades, this powerful biopic offers a glimpse into the life of famed Cuban poet and novelist Reinaldo Arenas, an artist who was vilified for his homosexuality in Fidel Castro's Cuba.
20 August 1997
After being released from a psychiatric institution, a man tries to redeem himself in the eyes of his now-ex wife from the events that led up to his incarceration.
25 January 1985
The true story of a disillusioned military contractor employee and his drug pusher childhood friend who became walk-in spies for the Soviet Union.
20 September 1991
Two brothers cannot overcome their opposite perceptions of life. One brother sees and feels bad in everyone and everything, subsequently he is violent, antisocial and unable to appreciate or enjoy the good things which his brother desperately tries to point out to him.
26 March 2025
Thirteen-year-old Marcielle lives on Marajó Island in the heart of the Amazon rainforest. To break a terrible cycle that imprisons the women around her in an isolated region, she must do the impossible to liberate herself and her younger sister from a dark abyss of silence held by her own family.
13 July 2002
Rosanna Arquette talks to various actresses about the pressures they face as women working in the entertainment industry.
