Entertainment
The Best Sean Penn Movies
List Rules
Vote for your favorite movies, regardless of critic reviews or how big the role was.
List of the best Sean Penn movies, ranked best to worst with movie trailers when available. Sean Penn's highest grossing movies have received a lot of accolades over the years, earning millions upon millions around the world. The order of these top Sean Penn movies is decided by how many votes they receive, so only highly rated Sean Penn movies will be at the top of the list. Sean Penn has been in a lot of films, so people often debate each other over what the greatest Sean Penn movie of all time is. If you and a friend are arguing about this then use this list of the most entertaining Sean Penn films to end the squabble once and for all.
If you think the best Sean Penn role isn't at the top, then upvote it so it has the chance to become number one. The greatest Sean Penn performances didn't necessarily come from the best movies, but in most cases they go hand in hand.
List films include Up at the Villa, This So-Called Disaster and many more.
"This list answers the questions, "What are the best Sean Penn movies?" and "What are the greatest Sean Penn roles of all time?"Ranked by
1Sean Penn, Tim Robbins, Kevin Bacon- Released: 2003
- Directed by: Clint Eastwood
When the daughter (Emmy Rossum) of ex-con Jimmy Marcus (Sean Penn) is murdered, two of his childhood friends from the neighborhood are involved. Dave (Tim Robbins), a blue-collar worker, was the last ...more
2Sean Penn, Jennifer Jason Leigh, Judge Reinhold- Released: 1982
- Directed by: Amy Heckerling
Stacy Hamilton (Jennifer Jason Leigh) is a pretty, but inexperienced, teen interested in dating. Given advice by her uninhibited friend, Linda Barrett (Phoebe Cates), Stacy gets trapped in a love ...more- 3Al Pacino, Sean Penn, Penelope Ann Miller
- Released: 1993
- Directed by: Brian De Palma
A free man after years in prison, Carlito Brigante (Al Pacino) 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. Reconnecting ...more ![Dead Man Walking]()
4Susan Sarandon, Sean Penn, Robert Prosky- Released: 1995
- Directed by: Tim Robbins
As death row inmate Matthew Poncelet (Sean Penn) nears his execution date, he calls upon Sister Helen Prejean (Susan Sarandon) to help him with one last appeal, maintaining that he is innocent of the ...more![Bad Boys]()
5Sean Penn, Reni Santoni, Esai Morales- Released: 1983
- Directed by: Rick Rosenthal
Teen delinquent Mick O'Brien (Sean Penn) is sent to juvenile hall after unintentionally killing the younger sibling of a rival gang leader, Paco Moreno (Esai Morales), in a drug-deal con gone wrong. ...more![The Game]()
6Sean Penn, Michael Douglas, Spike Jonze- Released: 1997
- Directed by: David Fincher, Pedro Coutinho
The Game is a 1997 American mystery thriller film directed by David Fincher, starring Michael Douglas and Sean Penn, and produced by Propaganda Films and PolyGram Filmed Entertainment. It tells the ...more![I Am Sam]()
7Sean Penn, Michelle Pfeiffer, Dakota Fanning- Released: 2001
- Directed by: Jessie Nelson
"I Am Sam" is the compelling story of Sam Dawson (Sean Penn), a mentally-challenged father raising his daughter Lucy (Dakota Fanning) with the help of a unique group of friends. As Lucy turns seven ...more![Colors]()
8Sean Penn, Robert Duvall, Maria Conchita Alonso- Released: 1988
- Directed by: Dennis Hopper
In this gritty police drama from director Dennis Hopper, street-wise cop Bob Hodges (Robert Duvall) and hotheaded rookie Danny McGavin (Sean Penn) grapple with their new partnership on the ...more![21 Grams]()
9Sean Penn, Benicio Del Toro, Naomi Watts- Released: 2003
- Directed by: Alejandro González Iñárritu
In a film that plays with the idea of straightforward storytelling, a group of troubled people find that they are linked in unpredictable ways. Paul Rivers (Sean Penn) is an academic dealing with a ...more![The Thin Red Line]()
10Sean Penn, Adrien Brody, Jim Caviezel- Released: 1998
- Directed by: Terrence Malick
In 1942, Private Witt (Jim Caviezel) is a U.S. Army absconder living peacefully with the locals of a small South Pacific island. Discovered by his commanding officer, Sgt. Welsh (Sean Penn), Witt is ...more![At Close Range]()
11Sean Penn, Christopher Walken, Mary Stuart Masterson- Released: 1986
- Directed by: James Foley
Based on a true story, "At Close Range" follows the lives of the Whitewood family in rural Pennsylvania. Brothers Brad Jr. (Sean Penn) and Tommy (Chris Penn) are the sons of organized crime leader ...more![Milk]()
12Sean Penn, Emile Hirsch, Josh Brolin- Released: 2008
- Directed by: Gus Van Sant
In 1972, Harvey Milk (Sean Penn) and his then-lover Scott Smith leave New York for San Francisco, with Milk determined to accomplish something meaningful in his life. Settling in the Castro District, ...more![The Falcon and the Snowman]()
13Timothy Hutton, Sean Penn, David Suchet- Released: 1985
- Directed by: John Schlesinger
After his father (Pat Hingle) finds him a job at the CIA, Christopher Boyce (Timothy Hutton) discovers the less reputable side of the American government through handling classified documents. As he ...more![State of Grace]()
14Sean Penn, Ed Harris, Gary Oldman- Released: 1990
- Directed by: Phil Joanou
Gone for a decade, Terry Noonan (Sean Penn) is welcomed back into the fold in his Irish-American neighborhood in New York City. A one-time street tough, Terry is now an undercover officer targeting ...more![Casualties of War]()
15Michael J. Fox, Sean Penn, Don Harvey- Released: 1989
- Directed by: Brian De Palma
Pvt. Max Eriksson (Michael J. Fox) is stationed in Vietnam under Sgt. Tony Meserve (Sean Penn). Though Meserve saves Eriksson's life during battle, the two men clash when the callous senior officer ...more![Racing with the Moon]()
16Sean Penn, Elizabeth McGovern, Nicolas Cage- Released: 1984
- Directed by: Richard Benjamin
In their last weeks before deployment to World War II as Marines, teenage friends Henry Nash (Sean Penn) and Nicky (Nicolas Cage) try to make the best of the time they have left in their small ...more![Taps]()
17Timothy Hutton, George C. Scott, Ronny Cox- Released: 1981
- Directed by: Harold Becker
Bunker Hill Military Academy has been targeted by real estate developers for demolition. The students, outraged at the thought of their school being turned into condominiums, vow to fight back. Led ...more![This Must Be the Place]()
18Sean Penn, Frances McDormand, David Byrne- Released: 2011
- Directed by: Paolo Sorrentino
This Must Be the Place is a 2011 European drama film directed by Paolo Sorrentino, written by Sorrentino and Umberto Contarello and released in the U.S. in late 2012. It stars Sean Penn and Frances ...more- 19Mel Gibson, Sean Penn, Natalie Dormer
- Released: 2019
- Directed by: P.B. Shemran
The Professor and the Madman is a 2019 biographical drama film direted by P.B. Sherman, based on the 1998 book The Surgeon of Crowthorne by Simon Winchester. In 1857, a professor begins compiling the ...more ![Sweet and Lowdown]()
20Sean Penn, Samantha Morton, Uma Thurman- Released: 1999
- Directed by: Woody Allen
Emmet Ray (Sean Penn) isn't an easy guy to be around -- among other things, he's inconsiderate and egomaniacal. He also happens to be a jazz guitarist with undeniable talent, and despite his many ...more![U Turn]()
21Jennifer Lopez, Sean Penn, Claire Danes- Released: 1997
- Directed by: Oliver Stone
U Turn is a 1997 American neo-noir crime thriller film directed by Oliver Stone and starring Sean Penn, Billy Bob Thornton, Jennifer Lopez, Jon Voight, Powers Boothe, Joaquin Phoenix, Claire Danes, ...more![The Weight of Water]()
22Catherine McCormack, Sarah Polley, Sean Penn- Released: 2000
- Directed by: Kathryn Bigelow
Kathryn Bigelow's intense and sexually charged drama of repression, love and loss. Juxtaposing the past and the present, "The Weight of Water" is about a 19th century murder and a contemporary woman ...more![The Tree of Life]()
23Brad Pitt, Sean Penn, Jessica Chastain- Released: 2011
- Directed by: Terrence Malick
In this highly philosophical film by acclaimed director Terrence Malick, young Jack (Hunter McCracken) is one of three brothers growing up as part of the O'Brien family in small-town Texas. Jack has ...more![We're No Angels]()
24Robert De Niro, Sean Penn, Demi Moore- Released: 1989
- Directed by: Neil Jordan
Ned (Robert De Niro) and Jim (Sean Penn) are convicts who get their shot at freedom when they unexpectedly escape from prison along with a killer. The two fugitives head north towards the Canadian ...more- 25Josh Brolin, Ryan Gosling, Nick Nolte
- Released: 2013
- Directed by: Ruben Fleischer
Ruthless, Brooklyn-born mobster Mickey Cohen (Sean Penn) has 1949 Los Angeles in an iron fist, as he accumulates a fortune from drugs, prostitution and gambling. Cohen has an army of paid goons at ...more
