| 8.0 |  | The Game | 1997 | Drama Mystery Thriller | David Fincher | Michael Douglas Deborah Kara Unger Sean Penn | * 3.8/5 |
| 7.9 | | Milk | 2008 | Biography Drama | Gus Van Sant | Sean Penn Josh Brolin Emile Hirsch | * 3.8/5 |
| 7.4 | | At Close Range | 1986 | Crime Drama | James Foley | Sean Penn Christopher Walken Mary Stuart Masterson | * 3.7/5 |
| 7.0 | | Colors | 1988 | Action Crime Drama Drama Romance Thriller | Dennis Hopper | Sean Penn Robert Duvall Maria Conchita Alonso | * 3.7/5 |
| 7.0 | | The First | 2018 | Drama Sci-Fi Series | Deniz Gamze Ergüven | Sean Penn Natascha McElhone LisaGay Hamilton | * 3.4 /5 |
| 6.8 | | Racing With the Moon | 1984 | Comedy Drama Romance | Richard Benjamin | Sean Penn, Elizabeth McGovern, Nicolas Cage | * 3.3/5 |
| 5.1 | | The Last Face | 2016 | Drama Romance | Sean Penn | Charlize Theron Javier Bardem Brandon Phillips | * 2.4/5 |
| 8.4 | | Into the Wild | 2007 | Adventure Biography Drama | Sean Penn | Emile Hirsch Vince Vaughn Catherine Keener | * 3.8/5 |
| 8.1 | | Mystic River | 2003 | Crime Drama Mystery Mystery Thriller | Clint Eastwood | Sean Penn Tim Robbins Kevin Bacon | * 3.8/5 |
| 8.1 | | I Am Sam | 2001 | Drama | Jessie Nelson | Sean Penn Michelle Pfeiffer Dakota Fanning | * 3.8/5 |
| 8.0 | | The Thin Red Line | 1998 | Drama War | Terrence Malick | Jim Caviezel Sean Penn Nick Nolte | * 3.5/5 |
| 8.0 | v | Dogtown and Z Boys | 2001 | Documentary Sport | Stacy Peralta | Sean Penn Jay Adams Tony Alva | * 3.4/5 |
| 7.9 | | Dead Man Walking | 1995 | Crime Drama | Tim Robbins | Susan Sarandon Sean Penn Robert Prosky | * 3.7/5 |
| 7.8 | | The Professor and the Madman | 2019 | Biography Drama | Farhad Safinia | Mel Gibson Sean Penn Eddie Marsan | * 3.3 /5 |
| 7.7 | | Bad Boys | 1983 | Crime Drama Thriller | Rick Rosenthal | Sean Penn Reni Santoni Jim Moody | * 3.8/5 |
| 7.5 | | Sweet and Lowdown | 1999 | Comedy Drama Music | Woody Allen | Sean Penn Samantha Morton Woody Allen | * 3.9/5 |
| 7.5 | | Fast Times at Ridgemont High | 1982 | Comedy Drama | Amy Heckerling | Sean Penn Jennifer Jason Leigh Judge Reinhold | * 3.7/5 |
| 7.3 | | Casualties of War | 1989 | Crime Drama War | Brian De Palma | Michael J. Fox Sean Penn Don Harvey | * 3.4/5 |
| 7.2 | | U Turn | 1997 | Crime Drama Thriller | Oliver Stone | Sean Penn Jennifer Lopez Nick Nolte | * 3.1/5 |
| 7.1 | | Fair Game | 2010 | Biography Drama Thriller | Doug Liman | Naomi Watts Sean Penn Sonya Davison | * 3.5/5 |
| 6.8 | | The Falcon and the Snowman | 1985 | Biography Crime Drama Drama Thriller | John Schlesinger | Timothy Hutton Sean Penn Pat Hingle | * 3.4/5 |
| 6.6 | | Sweet Micky for President | 2015 | Documentary Music News | Ben Patterson | Ben Stiller Sean Penn Sarodj Bertin | - 9/10 |
| 6.5 | | The Interpreter | 2005 | Crime Mystery Thriller | Sydney Pollack | Nicole Kidman Sean Penn Catherine Keener | * 3.3/5 |
| 8.4 | | The Zen Diaries of Garry Shandling Part 2 | 2018 | Biography Comedy Comedy Documentary Drama | Judd Apatow | Garry Shandling Judd Apatow Kevin Nealon | |
| 8.3 | | Persepolis | 2007 | Animation Biography Drama Drama History War | Vincent Paronnaud | Chiara Mastroianni Catherine Deneuve Gena Rowlands | * 3.9/5 |
| 8.1 | | Being John Malkovich | 1999 | Comedy Drama Fantasy | Spike Jonze | John Cusack Cameron Diaz Catherine Keener | * 3.4/5 |
| 7.9 | v | Bukowski Born Into This | 2003 | Biography Documentary | John Dullaghan | Charles Bukowski Bono John Bryan | * 3.9/5 |
| 7.7 | | Cutting Edge the Magic of Movie Editing | 2004 | Documentary | Wendy Apple | Kathy Bates Zach Staenberg Jodie Foster | * 4.4/5 |
| 7.6 | | Before Night Falls | 2000 | Biography Drama Romance | Julian Schnabel | Javier Bardem Johnny Depp Olatz Lopez Garmendia | * 3.5/5 |
| 7.5 | | Grindhouse Death Proof | 2007 | Action Thriller | Quentin Tarantino | Kurt Russell Zoe Bell Rosario Dawson | * 3.5/5 |
| 7.1 | | Taps | 1981 | Drama | Harold Becker | George C. Scott Timothy Hutton Ronny Cox | * 3.7/5 |
| 7.1 | | Risky Business | 1983 | Comedy Crime Drama Drama Romance | Paul Brickman | Tom Cruise Rebecca De Mornay Joe Pantoliano | * 3.5/5 |
| 6.7 | | The Angry Birds Movie | 2016 | Action Adventure Adventure Animation Comedy Family | Clay Kaytis | Jason Sudeikis Josh Gad Danny McBride | * 3.9/5 |
| 6.4 | | Hounddog | 2007 | Drama Music | Deborah Kampmeier | Dakota Fanning David Morse Piper Laurie | * 3.3/5 |
| 6.3 | | The People Speak | 2009 | Documentary History | Anthony Arnove | Marisa Tomei Matt Damon Viggo Mortensen | * 3.7/5 |
| 6.6 | | The Human Experiment | 2013 | Documentary | Don Hardy, Dana Nachman | Sean Penn Don Hardy Dana Nachman | * 3.9/5 |
| 8.5 | v | Little House on the Prairie | 1979 | Drama Family Romance Romance Western | Michael Landon | Michael Landon Karen Grassle Melissa Gilbert | * 3.6/5 |
| 8.1 | | Carlito s Way | 1993 | Crime Drama Thriller | Brian De Palma | Al Pacino Sean Penn Penelope Ann Miller | * 3.9/5 |
| 8.0 | | 21 Grams | 2003 | Crime Drama Thriller | Alejandro G. Inarritu | Sean Penn Benicio Del Toro Naomi Watts | * 3.5/5 |
| 7.8 | | Babel | 2006 | Drama | Alejandro G. Inarritu | Brad Pitt Cate Blanchett Gael Garcia Bernal | * 3.3/5 |
| 7.7 | | The Secret Life of Walter Mitty | 2013 | Adventure Comedy Drama Drama Fantasy Romance | Ben Stiller | Ben Stiller Kristen Wiig Jon Daly | * 3.6/5 |
| 6.6 | | The Last Party | 1993 | Documentary History | Mark Benjamin | Robert Downey Jr. Bill Clinton Ann Palmer | - 7.6/10 |
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