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?"Notable directors that have worked with Sean Penn include names like Brian De Palma, Terrence Malick and Woody Allen. Movie fans who love Sean Penn have also been known to enjoy films starring Andrew Dice Clay and Josh Brolin.
list ordered by
- Mystic River is a 2003 American mystery drama film directed and scored by Clint Eastwood. It stars Sean Penn, Tim Robbins, Kevin Bacon, Laurence Fishburne, Marcia Gay Harden, and Laura Linney. The ...more
- 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
- Carlito's Way is a 1993 American drama film directed by Brian De Palma, based on the novels Carlito's Way and After Hours by Judge Edwin Torres. The film adaptation was scripted by David Koepp. It ...more
- 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
- 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
- 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
- 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 is a 1998 American ensemble epic film written and directed by Terrence Malick. Based on the novel by James Jones, it tells a fictionalized version of the Battle of Mount Austen, ...more
- Bad Boys is a 1983 drama film written by Richard Di Lello and directed by Rick Rosenthal.
- 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
- 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
- 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
- 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
- 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
- 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
- I Am Sam is a 2001 American drama film directed by Jessie Nelson. A mentally handicapped man (Sean Penn) fights for custody of his 7-year-old daughter (Dakota Fanning) and in the process teaches his ...more
- Milk is a 2008 American biographical film based on the life of gay rights activist and politician Harvey Milk, who was the first openly gay person to be elected to public office in California, as a ...more
- 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
- 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
- Eddie (Sean Penn) is a confused and reckless man with a group of equally problematic friends. His roommate, caustic and sleazy Mickey (Kevin Spacey), is sleeping with Eddie's love, Darlene (Robin ...more
- 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
- Judgment in Berlin is a 1988 drama film written by Herbert J. Stern, Joshua Sinclair and Leo Penn, and directed by Leo Penn.
- During the Vietnam War, numerous U.S. soldiers wrote to friends and loved ones who were waiting back home for their safe return. This documentary takes a deeper look into the letters that were sent ...more
- A richly imagined journey into the life and writings of brilliant Cuban author and exile Reinaldo Arenas. It spans the whole of Arenas' life, from his rural childhood and his early embrace of the ...more
- 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
