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Jake Gyllenhaal on Picking Roles, Filming in Boston, and Creating Characters

Plus: what it’s like to work with Tom Ford

Annual Charity Day Hosted By Cantor Fitzgerald, BGC and GFI - BGC Office - Inside Photo by Dave Kotinsky/Getty Images for Cantor Fitzgerald

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).

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