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1. The Day After Tomorrow (2004)
directed by Roland Emmerich
featuring Dennis Quaid, Jake Gyllenhaal, Ian Holm, Emmy Rossum, Sela Ward
Directed by Roland Emmerich, this mega-budget, special-effects-laden epic revolves around the onset of an international series of crises brought on ... More
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2. Brokeback Mountain (2005)
directed by Ang Lee
featuring Heath Ledger, Jake Gyllenhaal, Michelle Williams, Anne Hathaway, Linda Cardellini
Ang Lee's adaptation of E. Annie Proulx's story Brokeback Mountain stars Jake Gyllenhaal and Heath Ledger as young cowboys named Jack Twist and Ennis ... More
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3. Donnie Darko (2001)
directed by Richard Kelly
featuring Jake Gyllenhaal, Jena Malone, Mary McDonnell, Holmes Osborne, Maggie Gyllenhaal, Drew Barrymore, Patrick Swayze
Donnie (Jake Gyllenhaal) is a bright and charming high-school student who also has a dark and willfully eccentric side; he does little to mask his ... More
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4. Proof (2005)
directed by John Madden
featuring Gwyneth Paltrow, Jake Gyllenhaal, Hope Davis, Anthony Hopkins
A woman struggles to come to terms with the potentially dangerous legacy of her late father in this drama based on the award-winning stage play by ... More
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5. Source Code (2011)
directed by Duncan Jones
featuring Jake Gyllenhaal, Michelle Monaghan, Vera Farmiga, Jeffrey Wright, Michael Arden
Jake Gyllenhaal headlines this sci-fi time-travel thriller directed by Moon's Duncan Jones from a script by Ben Ripley and Billy Ray. A bomb explodes ... More
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6. October Sky (1999)
directed by Joe Johnston
featuring Jake Gyllenhaal, Chris Cooper, Laura Dern, Chris Owen, William Lee Scott
NASA engineer Homer H. Hickam, Jr.'s autobiography provided the basis for this drama about a teenager coming of age at the dawn of the space race. In ... More
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7. Saturday Night Live: The Best of Amy Poehler (2009)
This hilarious Saturday Night Live collection celebrates the work of Amy Poehler, featuring her best-loved sketches and characters including "The ... More
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8. Prince of Persia: The Sands of Time (2010)
directed by Mike Newell
featuring Jake Gyllenhaal, Gemma Arterton, Ben Kingsley, Alfred Molina, Steve Toussaint
Ubisoft's popular video-game series of the same name gets adapted for the big screen in this sweeping fantasy adventure starring Jake Gyllenhaal and ... More
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9. Rendition (2007)
directed by Gavin Hood
featuring Jake Gyllenhaal, Reese Witherspoon, Alan Arkin, Peter Sarsgaard, Omar Metwally
The director of the Academy Award-winning 2006 crime drama Tsotsi returns to the helm with this tale of a Middle East CIA operative who begins to ... More
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10. Jarhead (2005)
directed by Sam Mendes
featuring Jake Gyllenhaal, Peter Sarsgaard, Lucas Black, Brian Geraghty, Jacob Vargas
A young man gets a crash course in the madness of war in this fact-based drama from director Sam Mendes. Anthony "Swoff" Swofford (Jake Gyllenhaal) ... More
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11. Zodiac (2007)
directed by David Fincher
featuring Mark Ruffalo, Jake Gyllenhaal, Robert Downey, Jr., Anthony Edwards, Brian Cox
The true story behind the murders that many crime scholars believe to be the most perplexing series of unsolved crimes in modern history comes to the ... More
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12. Brothers (2009)
directed by Jim Sheridan
featuring Tobey Maguire, Jake Gyllenhaal, Natalie Portman, Sam Shepard, Clifton Collins, Jr.
Jim Sheridan's film, adapted from Susanne Bier's 2004 movie, concerns Captain Sam Cahill (Tobey Maguire), a Marine who receives orders to ship out ... More
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13. Moonlight Mile (2002)
directed by Brad Silberling
featuring Jake Gyllenhaal, Dustin Hoffman, Susan Sarandon, Ellen Pompeo, Holly Hunter
Frequent television director Brad Silberling directs the romantic drama Moonlight Mile. Set in a Massachusetts town in the early '70s, Joe Nast (Jake ... More
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14. Love and Other Drugs (2010)
directed by Edward Zwick
featuring Jake Gyllenhaal, Anne Hathaway, Oliver Platt, Hank Azaria, Josh Gad
Handsome and charming pharmaceutical rep Jamie (Jake Gyllenhaal) falls head over heels for radiant free spirit Maggie (Anne Hathaway), and together ... More
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15. End of Watch (2012)
directed by David Ayer
featuring Jake Gyllenhaal, Michael Peņa, Frank Grillo, America Ferrera, Cody Horn
David Ayer's End of Watch stars Michael Peņa and Jake Gyllenhaal as a pair of L.A. cops and close friends who work to keep the streets safe. Shot in ... More
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16. The Good Girl (2002)
directed by Miguel Arteta
featuring Jennifer Aniston, Jake Gyllenhaal, John C. Reilly, Tim Blake Nelson, Zooey Deschanel
Director Miguel Arteta and writer Mike White, who had previously collaborated on Chuck and Buck, turn an eye toward suburban boredom with the quirky ... More
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17. Bubble Boy (2001)
directed by Blair Hayes
featuring Jake Gyllenhaal, Swoosie Kurtz, Marley Shelton, Danny Trejo, John Carroll Lynch
Jake Gyllenhaal, the young star of the critically well-received October Sky (1999), follows up that film with this offbeat comedy. Gyllenhaal stars ... More
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18. Lovely & Amazing (2002)
directed by Nicole Holofcener
featuring Catherine Keener, Brenda Blethyn, Emily Mortimer, Raven Goodwin, Jake Gyllenhaal
Nicole Holofcener, writer/director of the critically acclaimed Walking and Talking, shifts her focus from New York to Los Angeles for her second ... More
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19. Highway (2001)
directed by James Cox
featuring Jared Leto, Jake Gyllenhaal, Selma Blair, John C. McGinley
Two friends hit the road to escape some homicidal gangsters with a score to settle in this angsty Gen-X flick set against the backdrop of the mid- ... More
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20. The Man Who Walked Between the Towers (2005)
directed by Michael Sporn
featuring Jake Gyllenhaal
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