This ranking is based on an algorithm that combines various factors, including the votes of our users and search trends on the internet.

List of Sean Penn Movies: Ranked Best To Worst

1. Mystic River (2003)
46
1
Mystic River
R
46
1

Dave, a blue-collar worker who was abducted and sexually abused as a child 25 years earlier, is the prime suspect after the daughter of his neighborhood friend, ex-con Jimmy, is found dead. While their childhood friend Sean, now a homicide detective, investigating the crime, Jimmy takes law in his own hand by launching a separate investigation.

As:
Cast
Role:
Jimmy Markum
Director:
Genres:
Crime, Drama, Thriller, Mystery
Awards:
Academy Award for Best Actor in a Leading Role, Golden Globe Award for Best Performance by an Actor in a Motion Picture - Drama
2. Bad Boys (1983)
49
2
Bad Boys
R
49
2
As:
Cast
Role:
Mick O'Brien
Director:
Rick Rosenthal
Genres:
Thriller, Crime, Drama
Star Cast:
Ally Sheedy, Alan Ruck, Esai Morales, Reni Santoni, Jim Moody, Eric Gurry
3. Into the Wild (2007)
27
5
Into the Wild
R
27
5

Jon Krakauer’s 1996 non-fiction book - Into the Wild - is the basis of this movie. Christopher McCandless, a young graduate from Emory University, abandons the life of privilege and sets out on a cross country drive to explore the life in wilderness. He meets various people en route who all influence him in their own meaningful way.

As:
Producer, Director, Writer
Director:
Sean Penn
Genres:
Drama, Adventure, Biography
Star Cast:
4. I Am Sam (2001)
37
5
I Am Sam
PG-13
37
5

Sam Dawson is an intellectually disabled father raising his daughter Lucy with the help of a group of friends who also have disabilities. As Lucy grows up her intellectual superiority threatens their relationship. Things get more complicated when Lucy is placed in foster care but keeps coming back to her dad. 

As:
Cast
Role:
Sam Dawson
Director:
Jessie Nelson
Genres:
Drama
5. Carlito's Way (1993)
25
1
Carlito's Way
R
25
1

After drug dealer Carlito Brigante is released early from prison thanks to an exploitation by his sleazy lawyer friend Dave Kleinfeld, he pledges to mend his ways and rekindles his romance with former girlfriend Gail. However, despite repeated attempts to avoid temptations, he is eventually dragged into his former violent lifestyle while assisting Kleinfeld against an Italian Mafia boss.

As:
Cast
Role:
Kleinfeld
Director:
Genres:
Drama, Crime, Thriller
Star Cast:
6. The Game (1997)
28
3
The Game
R
28
3

The Game is a psychological thriller focusing on a lonely investment banker who is gifted a voucher for a unique game by his estranged brother that ends up wreaking havoc in his life. Starring Michael Douglas and Sean Penn as the two brothers, this film sees Douglas lose all his money in this game that becomes intrinsically connected to his real life.

As:
Cast
Role:
Conrad
Director:
Genres:
Thriller, Drama, Mystery
Star Cast:
Michael Douglas, Carroll Baker, Spike Jonze, James Rebhorn, Deborah Kara Unger
7. 21 Grams (2003)
22
0
21 Grams
R
22
0

After a fatal automobile accident, lives of three unrelated individuals intersect each other – a mathematics professor with a bad heart condition, a grieving mother with a reckless past, and a reformed former convict with faith in Jesus. The movie presents three simultaneous stories about the past and present of these three individuals entwined by the fateful accident. 

As:
Cast
Role:
Paul Rivers
Director:
Alejandro González Iñárritu
Genres:
Thriller, Drama, Crime
Star Cast:
Benicio Del Toro, Charlotte Gainsbourg, Naomi Watts, Danny Huston, Carly Nahon
8. Dead Man Walking (1995)
26
2
Dead Man Walking
R
26
2

Poncelet is awaiting execution for rape and murder of a teenage couple. As the day of his execution nears he writes to Sister Helen Prejean, hoping that she will help him with his appeal. Based on a true incident, the story focuses on Sister Prejean’s interaction with Poncelet and how she guided the arrogant and remorseless man to open admission of his crime and acceptance divine forgiveness. . 

As:
Cast
Role:
Matthew Poncelet
Director:
Tim Robbins
Genres:
Crime, Drama
Star Cast:
Susan Sarandon, Jack Black, Eva Amurri, Celia Weston, Raymond J. Barry
9. Fast Times at Ridgemont High (1982)
25
5
Fast Times at Ridgemont High
R
25
5

The coming-of-age story revolves around the lives of sophomores, Stacy Hamilton and Mark Ratner, and their friends, Linda and Mike. Stacy’s older brother, Brad, is also trying to figure things out after a break up while Stacy becomes pregnant. There is also Jeff Spicoli, a stoned surfer who is constantly going up against teacher Mr.Hand. 

As:
Cast
Role:
Jeff Spicoli
Director:
Amy Heckerling
Genres:
Comedy, Drama
10. The Thin Red Line (1998)
21
1
The Thin Red Line
TV-MA
21
1

Based on the eponymous novel by James Jones, The Thin Red Line is a war drama revolving around a group of soldiers fighting to capture Guadalcanal for the Allied Forces during World War II. Featuring a brilliant star cast of Sean Penn, John Travolta, George Clooney, Jim Caviezel, and more, this film focuses on American soldiers trying to capture Japanese bunkers.

As:
Cast
Role:
1st Sgt. Edward Welsh
Director:
Genres:
Drama, War
11. Milk (2008)
23
4
Milk
R
23
4

Through flashbacks, this biographical film records the career of Harvey Milk who became America's first openly gay person to be elected to public office on the San Francisco Board of Supervisors following a successful campaign led by his young partner and campaign manager Scott Smith. A year later, he is assassinated by his former conservative colleague Dan White.

As:
Cast
Role:
Harvey Milk
Director:
Gus Van Sant
Genres:
Drama, History, Biography, Romance
Awards:
Academy Award for Best Performance by an Actor in a Leading Role
12. State of Grace (1990)
23
3
State of Grace
TV-MA
23
3

Terry Noonan is an undercover police officer, who is targeting Frankie Flannery, a crime boss, who is also the brother of his best friend Jackie. However, soon, it seems that the mission will not be as easy for Terry as he had expected.

As:
Cast
Role:
Terry Noonan
Director:
Phil Joanou, Michael Lee Baron
Genres:
Crime, Drama, Action, Romance, Thriller
Star Cast:
Gary Oldman, Robin Wright, Ed Harris, John Turturro
14. Sweet and Lowdown (1999)
15
3
Sweet and Lowdown
PG-13
15
3

Emmett Ray is a famed jazz guitarist, who believes that love is a hindrance to his musical career. His views start to change after he develops affection for a shy and mute woman. However, shortly after he gains fame, he gets married to a wealthy socialite on a whim. 

As:
Cast
Director:
Genres:
Drama, Comedy, Music
Star Cast:
15. Before Night Falls (2000)
13
1
Before Night Falls
R
13
1

Before Night Falls is a biographical drama film which revolves around the life and the writings of a well-known Cuban author named Reinaldo Arenas. The film spans the whole area of his life, starting from his childhood and how he embraced the Revolution and later faced persecution, to his exile and death in the United States.

As:
Cast
Director:
Julian Schnabel
Genres:
Biography, Drama, Romance
Star Cast:
Javier Bardem, Johnny Depp, Diego Luna, Olatz López Garmendia, Giovanni Florido, Loló Navarro
16. The Professor and the Madman (2018)
9
1
The Professor and the Madman
9
1
As:
Cast
Role:
Dr. William Chester Minor
Director:
Farhad Safinia
Genres:
Drama, Biography, Mystery, Thriller
Star Cast:
Natalie Dormer, Mel Gibson, Ioan Gruffudd, Stephen Dillane
17. The Secret Life of Walter Mitty (2013)
10
1
The Secret Life of Walter Mitty
PG
10
1

Daydreamer Walter Mitty, the negative assets manager of Life magazine, finds his job at risk when the publication decides to go online. Matters complicate further when the negative 25 which is to be used for the cover of the last edition goes missing. To find Sean, the photographer, Walter steps out of his ordinary life and embarks on a real life adventurous journey around the world.

As:
Cast
Director:
Genres:
Drama, Comedy, Romance, Adventure, Fantasy
Star Cast:
Ben Stiller, Patton Oswalt, Shirley MacLaine, Kristen Wiig, Jon Daly, Kathryn Hahn, Terence Bernie Hines
18. Risky Business (1983)
13
4
Risky Business
R
13
4

Joel Goodson decides to cut loose with his friend Mike, after his parents go away for a trip. He ends up having sex with prostitute Lana, getting the house burgled, and crashing his father’s Porsche. He finally decides to turn the house into a brothel with Lana for a night to earn enough to pay for the repairs. 

As:
Cast
Director:
Paul Brickman
Genres:
Crime, Romance, Drama, Comedy
19. Colors (1988)
19
0
Colors
R
19
0

Colors is an action crime drama film which tells the story of an experienced cop and his hot-tempered rookie partner, who patrol the streets of Los Angeles, while attempting to keep the gang violence under control. While doing their job, both cops deal with issues such as racism.

As:
Cast
Role:
Danny McGavin
Director:
Genres:
Romance, Action, Thriller, Drama, Crime
Star Cast:
Mario Lopez, Damon Wayans, Don Cheadle, Robert Duvall, Maria Conchita Alonso, Randy Brooks, Grand L. Bush
21. Casualties of War (1989)
13
3
Casualties of War
R
13
3

This war drama film takes us to the Vietnam War, and it tells the story of Private Eriksson who must not only fight against the enemy but also his own squad leader, Sergeant Tony Meserve, when he orders the squad members to kidnap and rape a poor farm girl. 

As:
Cast
Role:
Sgt. Tony Meserve
Director:
Genres:
Crime, Drama, War
Star Cast:
22. Taps (1981)
9
2
Taps
PG
9
2
As:
Cast
Role:
Cadet Captain Alex Dwyer
Director:
Harold Becker
Genres:
Drama
Star Cast:
George C. Scott, Tom Cruise, Timothy Hutton, Ronny Cox
23. U Turn (1997)
15
2
U Turn
R
15
2

Bobby is heading to Vegas to pay off his gambling debts before the Russian mafia kills him. However, he is forced to stop in a town in Arizona, when his car breaks down. He gets caught in various problems after he meets Grace, a local resident. 

As:
Cast
Role:
Bobby Cooper
Director:
Genres:
Drama, Thriller, Crime
24. The Assassination of Richard Nixon (2004)
8
1
The Assassination of Richard Nixon
TV-MA
8
1

Based on real events, this crime thriller film tells the story of a furniture salesman in 1972, who comes up with a plan to kill the then-President of the US, Richard Nixon. His plan involves hi-jacking a plane to fly over the White House in order to drop a gas bomb.

As:
Cast
Role:
Samuel J. Bicke
Director:
Niels Mueller
Genres:
Biography, Thriller, Crime, Drama, History
Star Cast:
Don Cheadle, Naomi Watts, Jack Thompson, Brad William Henke
26. The Pledge (2001)
10
0
The Pledge
R
10
0

Retiring detective, Jerry Black, promises a mother to find the murderer of her young daughter. Unconvinced that it’s an open-and-shut case, Jerry buys petrol-pump, moves in that area where he discovers more cases and clues. As he grows closer to bartender Lori, her young daughter reports befriending a person nearer to suspect’s description. So now Jerry has to quickly nab the killer. 

As:
Producer, Director
Director:
Sean Penn
Genres:
Crime, Drama, Mystery, Thriller
27. This Must Be the Place (2011)
14
2
This Must Be the Place
R
14
2

This Must be The Place is a comedy drama film, which tells the story of a former rockstar who, after his father’s death, sets out to find the Nazi war criminal, who is responsible for his father’s humiliation during the Second World War.

As:
Cast
Role:
Cheyenne
Director:
Paolo Sorrentino
Genres:
Drama, Comedy
Star Cast:
Frances McDormand, Harry Dean Stanton, Olwen Fouere, Eve Hewson, Johnny Ward
28. 11'09''01 - September 11 (2002)
6
1
11'09''01 - September 11
6
1
As:
Director, Writer
Director:
Genres:
Drama
Star Cast:
Ernest Borgnine, Maryam Karimi, Mohamad Dolati, Agelem Habibi, Esmat Vahedi
29. The Falcon and the Snowman (1985)
11
3
The Falcon and the Snowman
R
11
3
As:
Cast
Role:
Daulton Lee
Director:
John Schlesinger
Genres:
Crime, Biography, Drama, Thriller
Star Cast:
John Ratzenberger, Timothy Hutton, Joyce Van Patten, Pat Hingle, Rob Reed
30. Gangster Squad (2013)
9
1
Gangster Squad
R
9
1

In 1949, Mobster Mickey Cohen rules the California criminal underworld and has even police and politicians in his pocket. A secret police unit called the Gangster Squad, comprising of Sergeant John O’Mara, Sergeant Jerry Wooters, Lieutenant Coleman Harris, Conwell Keeler, Max Kennard, and Navidad Ramirez finally manages to bring him down. 

As:
Cast
Role:
Mickey Cohen
Director:
Ruben Fleischer
Genres:
Thriller, Action, Drama, Crime
31. Fair Game (2010)
9
3
Fair Game
PG-13
9
3

Based on two memoirs, one by Valerie Plame and the other by her diplomat husband, the film follows the life of Valerie Plame, an intelligence officer involved in several important projects. She has been able to hide her profession from the outside world until husband’s article in a popular magazine angers the White House and her identity is leaked. 

As:
Cast
Role:
Joe Wilson
Director:
Doug Liman
Genres:
Thriller, Biography, Drama
Star Cast:
Sam Shepard, Naomi Watts, Sonya Davison, Vanessa Chong, Anand Tiwari
32. The Tree of Life (2011)
6
3
The Tree of Life
PG-13
6
3

Critically acclaimed, experimental-drama film, The Tree of Life, is based in Texas in 1950s. It explores the story of a father, a mother and three brothers, through the eyes of the youngest son Jack. He takes the viewers into his life and mind as a middle-aged adult, who is going through an existential crisis, while reminiscing his childhood struggles.

As:
Cast
Role:
Jack
Director:
Genres:
Drama, Fantasy
Star Cast:
Jessica Chastain, Brad Pitt, Hunter McCracken, Laramie Eppler
33. The Interpreter (2005)
10
3
The Interpreter
PG-13
10
3

Silvia Broome, who grew up in South Africa, is an expert in various languages and thus works as an interpreter in the United Nations. One day, she accidentally overhears a conversation around a plan to kill the African dictator Zuwanie who is accused of genocide. Secret Service agent Keller and Woods are tasked to protect him. Keller, however has his doubts about Silvia’s claim and intention.

As:
Cast
Role:
Tobin Keller
Director:
Genres:
Thriller, Crime, Mystery
Star Cast:
Nicole Kidman, Sydney Pollack, Catherine Keener, Jesper Christensen, Yvan Attal
34. The Crossing Guard (1995)
9
1
The Crossing Guard
R
9
1
As:
Producer, Director, Writer
Director:
Sean Penn
Genres:
Thriller, Drama
Star Cast:
Robin Wright, Jack Nicholson, David Morse, Anjelica Huston, Piper Laurie
35. We're No Angels (1989)
14
2
We're No Angels
PG-13
14
2

Jim and Ned are two convicts who manage to escape from prison along with a killer. They decide to head north towards the Canadian border, but they are soon mistaken for priests. They play along and take up residency at a monastery, but things get complicated when Ned falls for Molly, a local girl.  

As:
Cast
Role:
Jim
Director:
Neil Jordan
Genres:
Comedy, Crime
Star Cast:
Robert De Niro, Demi Moore, Hoyt Axton, Bruno Kirby
36. All the King's Men (2006)
7
1
All the King's Men
PG-13
7
1

Based on an award-winning novel of the same name, this political drama film revolves around the life of Willie Stark, an idealistic lawyer, who becomes the governor of Louisiana. However, as he rises to power, he also finds himself involved with corruption.

As:
Cast
Role:
Willie Stark
Director:
Steven Zaillian
Genres:
Thriller, Drama
37. The Gunman (2015)
11
2
The Gunman
R
11
2

The Gunman is an action drama film, which tells the story of an assassin, who is forced to go into hiding after he kills the minister of mines in Congo.  Years later, when he returns to the country as a charity worker, he becomes the target of a hit squad himself.  

As:
Cast, Producer, Writer
Role:
Terrier
Director:
Pierre Morel
Genres:
Action, Thriller, Crime, Drama, Mystery
Star Cast:
Idris Elba, Javier Bardem, Ray Winstone, Mark Rylance, Jasmine Trinca
39. The Weight of Water (2000)
8
1
The Weight of Water
R
8
1
As:
Cast
Director:
Kathryn Bigelow
Genres:
Mystery, Crime, Thriller, Drama
Star Cast:
Elizabeth Hurley, Ciarán Hinds, Sarah Polley, Ulrich Thomsen, Richard Donat
43. The Beaver Kid 2 (1981)
3
1
The Beaver Kid 2
3
1
As:
Cast
Role:
Groovin' Larry
Director:
Trent Harris
Genres:
Short
44. What Just Happened (2008)
4
0
What Just Happened
R
4
0

What Just Happened is a comedy drama film which tells the story of Ben, a veteran Hollywood producer, who is going through a tough time, but struggles to finish his new film, while also dealing with his personal problems. Meanwhile, he is also trying to maintain a relationship with his young daughter.

As:
Cast
Role:
Sean Penn
Director:
Barry Levinson
Genres:
Comedy, Drama
45. Crackers (1984)
2
0
Crackers
PG
2
0

A low-paying pawn shop employee, Weslake joins in on a plan by an amateur musician Dillard, an illegal immigrant Ramon, a pimp named Broadwalk, and a homeless man named Turtle to break into the large safe in the pawn shop. But the rewards might not be what they expected. 

As:
Cast
Role:
Dillard
Director:
Louis Malle
Genres:
Thriller, Crime, Comedy, Adventure
Star Cast:
Christine Baranski, Donald Sutherland, Wallace Shawn, Jack Warden, Larry Riley
47. Summerspell (1983)
2
0
Summerspell
2
0
As:
Cast
Director:
Lina Shanklin
Genres:
Biography, Drama
Star Cast:
Louise Davis, Edna Wisdom, Vernon Lafon, Ed Wright
51. Shanghai Surprise (1986)
2
0
Shanghai Surprise
PG-13
2
0
As:
Cast
Role:
Glendon Wasey
Director:
Jim Goddard
Genres:
Romance, Crime, Drama, Adventure
Star Cast:
Richard Griffiths, Madonna, Paul Freeman, Philip Sayer
52. Witch Hunt (2008)
2
0
Witch Hunt
2
0
As:
Producer
Director:
Dana Nachman, Don Hardy Jr.
Genres:
Documentary, Crime
Star Cast:
Jack Cummings, Jackie Cummings, Allen Grafton, Ed Jagels, Brenda Kniffen
53. The Human Experiment (2013)
4
0
The Human Experiment
4
0
As:
Cast, Producer
Role:
Narrator
Director:
Dana Nachman, Don Hardy Jr.
Genres:
Documentary
54. Love Hate Love (2011)
2
0
Love Hate Love
2
0
As:
Producer
Director:
Dana Nachman
Genres:
Documentary
55. Judgment in Berlin (1988)
8
1
Judgment in Berlin
PG
8
1
As:
Cast
Director:
Leo Penn
Genres:
Drama
Star Cast:
Martin Sheen, Max Gail, Sam Wanamaker, Carl Lumbly
56. Sound of Sun (2016)
2
0
Sound of Sun
2
0
As:
Cast
Role:
Man
Director:
Eva Dolezalova
Genres:
Short, Fantasy, Drama, Mystery
Star Cast:
Suki Waterhouse, Eva Dolezalova
57. Americans (2012)
3
0
Americans
3
0
As:
Cast, Writer
Role:
Commie
Director:
Jameson Stafford
Genres:
Short
Star Cast:
Kid Rock, Bianca Siavoshy, Rod Simmons, Shanna Collins
58. Loved (1997)
2
0
Loved
PG-13
2
0
As:
Cast, Producer
Role:
Man on the Hill
Director:
Erin Dignam
Genres:
Drama, Thriller
Star Cast:
Robin Wright, William Hurt, Evelyn Dignam, Anthony Lucero
59. Cruise Control (1992)
2
1
Cruise Control
2
1
As:
Cast
Role:
Jeffrey
Director:
Matt Palmieri
Genres:
Short
Star Cast:
Ed Begley Jr., Harry Dean Stanton, Max Perlich, C.M. Talkington

TV Movie(s)

61. Hellinger's Law (1981)
4
1
Hellinger's Law
4
1
As:
Cast
Director:
Leo Penn
Genres:
Drama, Crime
Star Cast:
Telly Savalas, Rod Taylor, Ja'net DuBois, Roy Poole

Animation(s)

Persepolis (2007)
Persepolis
PG-13
Plot:

Based on the life of Marjane Satrapi, the animated movie follows her journey from a young girl in Iran to growing up to be a punk-loving teenage and leaving for Paris. When she returns to Iran, it has become more intolerant with religious absurdities and liberals are being executed.  

As:
Cast
Director:
Marjane Satrapi, Vincent Paronnaud
Genres:
Drama, Biography, War, Animation
Star Cast:
Catherine Deneuve, Gena Rowlands, Chiara Mastroianni, Danielle Darrieux, Simon Abkarian
Angry Birds (2016)
Angry Birds
PG
Plot:

The flightless birds of the Bird Island are a happy population, except for the three outcasts – hot-tempered Red, speedy Chuck and explosive Bomb. When the mysterious green piggies arrive on their island, everyone happily welcomes them. But Red suspects that there is some covert reason behind their visit. With Chuck and Bomb, Red sets out to get to the bottom of it. 

As:
Cast
Director:
Clay Kaytis, Fergal Reilly
Genres:
Comedy, Action, Adventure, Animation, Family

TV Shows and Videos

Peter Gabriel: Play (2004)
Peter Gabriel: Play
As:
Director
Director:
Sean Penn, Peter Medak, David Mallet, Brett Leonard, Marcelo Anciano
Genres:
Music
Star Cast:
Christopher McDonald, Kate Bush, Peter Gabriel, Kevan Allen, Youssou N'Dour
Bruce Springsteen: The Complete Video Anthology 1978-2000 (2001)
Bruce Springsteen: The Complete Video Anthology 1978-2000
As:
Director
Director:
Brian De Palma, Sean Penn, Adam Bernstein, Tim Robbins, Jonathan Demme
Genres:
Biography, Music, Documentary
Star Cast:
Courteney Cox, Clarence Clemons, Bruce Springsteen, Roy Bittan, Danny Federici
Cool Blue (1990)
Cool Blue
R
As:
Cast
Director:
Richard Shepard, Mark Mullin
Genres:
Comedy, Romance, Thriller
Star Cast:
Woody Harrelson, Hank Azaria, Paul Lussier, Ely Pouget
Shania Twain: Dance with the One That Brought You (1993)
Shania Twain: Dance with the One That Brought You
As:
Director
Director:
Sean Penn
Genres:
Romance, Western, Short, Music
Star Cast:
Charles Durning, Shania Twain

Sean Penn Awards

Academy Awards
Milk Best Performance by an Actor in a Leading Role 2009
Mystic River Best Actor in a Leading Role 2004
Golden Globe Awards
Mystic River Best Performance by an Actor in a Motion Picture - Drama 2004