Gyllenhaal received further recognition for roles in Zodiac (2007), Brothers (2009), Prince of Persia: The Sands of Time (2010), Love & Other Drugs (2010), for which he was nominated for the Golden Globe Award for Best Actor – Motion Picture Musical or Comedy, Source Code (2011), End of Watch (2012), Prisoners and Enemy (both 2013), Nightcrawler (2014), Southpaw (2015), and Nocturnal Animals (2016), for which he was nominated for the BAFTA Award for Best Actor in a Leading Role.
For Nightcrawler, his performance was widely acclaimed and received rave reviews from critics and he was nominated for the Golden Globe Award for Best Actor – Motion Picture Drama, the Screen Actors Guild Award for Outstanding Performance by a Male Actor in a Leading Role, and the BAFTA Award for Best Actor in a Leading Role.
Shortly after the 2006 Academy Awards, Gyllenhaal was invited to join the Academy in recognition of his acting career.
Gyllenhaal expressed mixed feelings about the experience of being directed by Ang Lee in Brokeback Mountain but generally had more praise than criticism for Lee's directing style.
Gyllenhaal's performance was well received by critics; Gary Mairs of Culture Vulture wrote 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 Pilot Kelston in 2002's Highway alongside Jared Leto.On his 13th birthday, Gyllenhaal performed a "barmitzvah-like act, without the typical trappings", volunteering at a homeless shelter because his parents wanted to give him a sense of gratitude for his privileged lifestyle.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.While complaining of the way Lee tended to disconnect from his actors once filming began, Gyllenhaal praised his encouraging direction of the actors and sensitive approach to the material. I've never really been attracted to men sexually, but I don't think I would be afraid of it if it happened. The following year, Gyllenhaal played the lead role in the movie adaptation of the video game Prince of Persia: The Sands of Time, produced by Jerry Bruckheimer and released by Disney on May 28, 2010, and in the romantic comedy Love & Other Drugs, released on November 24, 2010, for which he received a Golden Globe Award nomination.