Due to his parents’ insistence that he pursue summer jobs to support himself, he took positions as a busboy and lifeguard at a restaurant run by a family friend. “I do have parents who constantly supported me in certain ways,” Gyllenhaal added, expressing how much his parents fostered artistic expression. They lacked in other respects. My family has always excelled in expressiveness and creativity. After graduating from Harvard-Westlake School in Los Angeles in 1998, Gyllenhaal went on to study philosophy and Eastern religions at Columbia University, where his mother had also graduated and where his sister was a senior.

 Gyllenhaal left school after two years to focus on his acting career, but he has stated that he plans to eventually complete his degree. In October Sky, Joe Johnston’s 1999 film adaptation of Homer Hickam’s autobiography Rocket Boys, Gyllenhaal played the starring part of a teenage West Virginian who was trying to get into a science program so he wouldn’t have to work as a coal miner. The Sacramento News and Review referred to Gyllenhaal’s $32 million box office take as his “breakout performance” for the well-received movie.