His performance was described by one critic as "silly, cliched and straight to video".Gyllenhaal later starred in the Touchstone Pictures romantic comedy Bubble Boy, which was loosely based on the story of David Vetter.The story, which received mixed reviews, 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". He also auditioned to be Batman for the blockbuster Batman Begins and Heath Ledger play young men who meet as sheep herders and embark upon a sexual relationship that begins in the summer of 1963 and lasts for 20 years.Along with their mother, Jake and Maggie appeared in two episodes of Molto Mario, an Italian cooking show on the Food Network. Gyllenhaal graduated from the Harvard-Westlake School in Los Angeles in 1998, then attended Columbia University, where his sister was a senior and from which his mother had graduated, to study Eastern religions and philosophy.
Gyllenhaal said his parents encouraged artistic expression: "I do have parents who constantly supported me in certain ways. Definitely, it's in expression and creativity where my family has always been best at." As a child, Gyllenhaal was regularly exposed to filmmaking due to his family's deep ties to the industry.His breakthrough performance was as Homer Hickam in October Sky (1999) and he garnered an Independent Spirit Award nomination for Best Male Lead for playing the title character in the indie cult hit Donnie Darko (2001), in which he played a psychologically troubled teenager alongside his older sister, Maggie Gyllenhaal.He subsequently appeared in another indie film, The Good Girl (2002) and the climate fiction-disaster film The Day After Tomorrow (2004), portraying a student caught in a cataclysmic climate event.He was allowed to appear in his father's films several times.