Jake Gyllenhaal on Picking Roles, Filming in Boston, and Creating Characters (Ep. 265)

HBO and The Ringer’s Bill Simmons is joined by Jake Gyllenhaal to discuss auditioning for The Sandlot (7:00), his new film Stronger (13:00), shooting on set in Boston (24:00), role models in acting (30:00), Donnie Darko (38:00), the social importance of Brokeback Mountain (48:00), Heath Ledger’s legacy (58:00), filming a sports movie in Southpaw (1:10:00), working with Tom Ford (1:14:00), and shooting a sibling thriller with his sister, Maggie (1:18:00).