While Gyllenhaal continued to earn acting roles, his parents insisted that he keep it real. Just to remind him how privileged he was, they threw his bar mitzvah at a homeless shelter. Gyllenhaal also took summer jobs, including working as a busboy and lifeguard. (Carolyn Cole / Los Angeles Times)
Jake is the younger brother of actress Maggie Gyllenhaal. The two played on-screen siblings in 2001’s “Donnie Darko.” (Lucy Nicholson / AFP/Getty)
Reuniting with a “Brokeback” costar, Gyllenhaal portrays drug representative Jamie Randall opposite Anne Hathaway as Parkinson’s-inflicted Maggie Murdock in this romantic comedy based on the nonfiction book “Hard Sell: The Evolution of a Viagra Salesman.” (Carolyn Cole / Los Angeles Times)