Jake Gyllenhaal comes from a show business family, and he has been acting from a very young age. He has an extremely likable way about him, and his acting talents are top-notch. Gyllenhaal continues to wow audiences with his captivating performances year after year. His career has spanned across all genres, and he even proved with Netflix’s The Guilty, that he has the ability to carry an entire film through his performance. Gyllenhaal has some very exciting projects in the works, including Michael Bay’s upcoming film Ambulance. He will also be acting opposite Alexander Ludwig in Guy Ritchie’s war thriller, The Interpreter.
Gyllenhaal has already had a long and successful career, and it’s undoubtedly going to continue to flourish. In the 2000s, his career really began to take off. He showed us that he was capable of playing dark characters just as well as comedic ones. Throughout this decade, he worked with several prominent directors, including Sam Mendes, Ang Lee, and David Fincher. At the same time, Gyllenhaal earned an Academy Award nomination for Best Supporting Actor for his performance in Brokeback Mountain. With each performance, Gyllenhaal seems to be getting better and better, and audiences are always eager to see what he will do next. Let’s dive into to Jake Gyllenhaal’s best movies of the 2000s, ranked.
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9 Bubble Boy
Buena Vista Pictures
The comedy film Bubble Boy follows Jimmy Livingston (Gyllenhaal) who has no immune system and is confined to a plastic bubble. On a quest to stop his true love’s wedding, Jimmy travels across the country, meeting several interesting characters along the way. The goofy film is hilarious from beginning to end and has some heartfelt moments at the same time. Gyllenhaal proved that he is perfectly capable of taking on a comedic role.
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8 Moonlight Mile
Moonlight Mile is an endearing story about navigating life and dealing with grief. The film follows Joe Nast (Gyllenhaal) who befriends the parents of his dead fiancée. During his time of grief, Joe slowly learns how to move on with his life. The film portrays the complexities of life and the importance of connection while dealing with death. The film also features several great performances from Dustin Hoffman and Susan Sarandon.
7 Brothers
Columbia Pictures
Jake Gyllenhaal stars in Brothers, opposite Natalie Portman and Tobey Maguire. After Tommy (Gyllenhaal) learns that his brother Sam (Maguire) is presumed dead at war, he steps in to assist his brother’s widow Grace (Portman) and her children. After Sam returns home, tensions rise and drama ensues after he learns about the relationship between Tommy and Grace. It is a very dramatic and thought-provoking film that features one of Maguire’s best performances.
6 Proof
Miramax Films
John Madden’s Proof follows the daughter (Gwyneth Paltrow) of a brilliant mathematician (Anthony Hopkins) who works to uncover several mysteries about his life. Along the way, she forms a relationship with her father’s ex-student (Gyllenhaal). The movie showcases the importance of cherishing the ones you love, while also finding the strength to move on after death. At the same time, the movie is filled with conflict and romance. It is an endearing story that features fine performances from the cast.
5 The Good Girl
Fox Searchlight Pictures
Acclaimed writer/director Mike White wrote The Good Girl’s screenplay starring Jennifer Aniston and Jake Gyllenhaal. The story follows an unhappily married woman who begins an affair with a younger coworker who is obsessed with Holden Caulfield. The film is a great blend of comedy and drama, and it is carried by strong performances and White’s sharp dialogue. The story focuses on the turmoils of everyday life and the yearning of wanting more. John C. Reilly, Zooey Deshanel, and John Carrol Lynch also star in this fantastic black comedy.
4 Donnie Darko
Flower Films
Although Donnie Darko was not a box-office success upon its initial release, it has since become a cult classic with a dedicated following. The story is about a troubled teen (Gyllenhaal) who begins to have disturbing visions, causing him to commit crimes. Donnie Darko is a highly original film that is fascinating from beginning to end. It focuses on several interesting topics including time travel and wormholes. The cast also includes Jena Malone and Gyllenhaal’s sister Maggie.
3 Zodiac
Paramount Pictures
David Fincher’s film depicts the investigation behind the Zodiac murders in California. Gyllenhaal plays a cartoonist who becomes obsessed with Zodiac and works alongside journalist Paul Avery (Robert Downey Jr.) to track him down. The film is beautifully shot and features a fascinating and thrilling story with scary moments along the way. Zodiac is certainly one of Fincher’s most underrated films of his career.
2 Jarhead
Universal Pictures
Sam Mendes defined modern-day war with his critically acclaimed film, Jarhead. The film follows a group of Marines during the Gulf War and focuses on the mental torment that many Marines go through. It is a psychological war film that is unique compared to other films in the genre. Gyllenhaal is fantastic from beginning to end, and his performance totally showcased the mindset of a modern soldier.
1 Brokeback Mountain
Focus Features
Gyllenhaal earned his first Oscar nomination for his performance in Ang Lee’s Brokeback Mountain. The heartbreaking love story, also starring Heath Ledger, follows the relationship between two cowboys over the course of decades. Every aspect of the film including the story, cinematography, and direction is masterful. Brokeback Mountain was a career-best for Lee and featured one of Gyllenhaal’s greatest performances to date.
