Cinema Experts

"The truth is most of the films that make a lot of money no one remembers, and I'm not interested in making films that no one remembers."
During childhood, Gyllenhaal had regular exposure to filmmaking due to his family's deep ties to the industry. As an 11-year-old he made his acting debut as Billy Crystal's son in the 1991 comedy film City Slickers. Gyllenhaal appeared in the 1993 film A Dangerous Woman (along with sister Maggie), in a 1994 episode of Homicide: Life on the Street, and in the 1998 comedy Homegrown. Along with their mother, Jake and Maggie appeared in two episodes of Molto Mario, an Italian cooking show on the Food Network.
Gyllenhaal's first lead role was in October Sky, Joe Johnston's 1999 adaptation of the Homer Hickam autobiography Rocket Boys, in which he portrayed a young man from West Virginia striving to win a science scholarship to avoid becoming a coal miner. The film earned $32 million and was described in the Sacramento News and Review as Gyllenhaal's "breakout performance."
Donnie Darko, Gyllenhaal's second major film, was not a box office success upon its initial 2001 release, but eventually became a cult favorite. The film, directed by Richard Kelly, is set in 1988 and stars Gyllenhaal as a troubled teenager who, after narrowly escaping death, experiences visions of a 6 foot (1.8 m) tall rabbit named Frank who tells him that the world is coming to an end. Gyllenhaal's performance was well-received by critics; Dan Kois of Salon.com claimed that "Gyllenhaal manages the difficult trick of seeming both blandly normal and profoundly disturbed, often within the same scene".
After the critical success of Donnie Darko, Gyllenhaal's next role was as the lead character in 2002's Highway, a film ignored by audiences and critics alike. His performance was described by one critic as "silly, cliched and straight to video".
Gyllenhaal had more success starring opposite Jennifer Aniston in The Good Girl, which premiered at the 2002 Sundance Film Festival; he also starred in Lovely & Amazing with Catherine Keener. In both films he plays an unstable character who begins a reckless affair with an older woman. Gyllenhaal later described these as "teenager in transition" roles. Gyllenhaal later starred in the Touchstone Pictures romantic comedy Bubble Boy, which was loosely based on the story of David Vetter. The film portrays the title character's adventures as he pursues the love of his life before she marries the wrong man. The film was panned by critics, with one calling it an "empty-headed, chaotic, utterly tasteless atrocity".
Following Bubble Boy, Gyllenhaal starred opposite Dustin Hoffman and Susan Sarandon in Moonlight Mile, as a young man coping with the death of his fiancée and the grief of her parents. The story, which received mixed reviews, is loosely based on writer/director Brad Silberling's personal experiences following the murder of girlfriend Rebecca Schaeffer.
Gyllenhaal was almost cast as Spider-Man for Spider-Man 2 due to director Sam Raimi's concerns that Tobey Maguire, who had a back injury, risked paralysis from the stuntwork the movie required. Maguire recovered, however, and the sequel was shot without Gyllenhaal.
Instead, Gyllenhaal starred in the blockbuster The Day After Tomorrow in 2004, co-starring Dennis Quaid as his father.
In his theatrical debut Gyllenhaal starred on the London stage in Kenneth Lonergan's revival of This is Our Youth. Gyllenhaal said, "Every actor I look up to has done theatre work, so I knew I had to give it a try." The play, which had been a critical sensation on Broadway, ran for eight weeks in London's West End. Gyllenhaal received favorable critical reviews and an Evening Standard Theatre Award in the category "Outstanding Newcomer".
2005 was a prolific year for Gyllenhaal, who starred in the critically praised films Proof, Jarhead, and Brokeback Mountain. In Proof, featuring Gwyneth Paltrow and Anthony Hopkins, Gyllenhaal played a graduate student in mathematics who tries to convince Paltrow's character to publish a revolutionary proof to a problem puzzling the mathematicians' community. In Jarhead, Gyllenhaal played against his usual "sensitive yet disturbed" type by displaying an aggressive masculinity as a violent U.S. Marine during the first Gulf War. Public reaction to this film was muted due to Gyllenhaal's simultaneous appearance in Brokeback Mountain.
In Brokeback Mountain, Gyllenhaal and Heath Ledger play two sheep herders who, after overcoming initial reluctance, have a homosexual relationship during the 1960s and 1970s. The film was often referred to in the media with the shorthand phrase "the gay cowboy movie". The film won the Golden Lion prize at the Venice Film Festival. The film went on to win four Golden Globe Awards, four British Academy of Film and Television Arts (BAFTA) Awards, and three Academy Awards. Gyllenhaal was nominated for an Academy Award in the category of Best Supporting Actor for his performance, but lost to George Clooney for Syriana. Gyllenhaal also won the Best Supporting Actor BAFTA for the same role and received a Best Supporting Actor nomination and Best Film Ensemble nomination from the Screen Actors Guild. Shortly after the 2006 Academy Awards, Gyllenhaal was invited to join the Academy in recognition of his acting career. Most recently, Gyllenhaal was awarded the 2006 Young Artist Award for Artistic Excellence by The Americans for the Arts National Arts Awards for his role.