Tom Gregory (producer) Lincoln. Hollywood memorabilia in his collection are the cowboy shirts worn by Heath Ledger and Jake Gyllenhaal in the film Brokeback Mountain as well as the suit, shirt, tie and campaign pin worn by Sean Penn during his Oscar-winning performance in Milk The auction bids for these items have benefited different children's charities. Tom Gregory's philanthropic involvement also spans both coasts. In Los Angeles, he teaches after-school acting classes for preteens, drawing on his own acting experience gained in repertory companies in East Hampton, New York, Delray Beach, Florida, and across the United States. In Southampton New York, Tom Gregory
Jake Gyllenhaal would have required him to leave home for two months. In subsequent years, his parents allowed him to audition for roles but regularly forbade him to take them if he were chosen. He was allowed to appear in his father's films several times. Gyllenhaal appeared in the 1993 film "A Dangerous Woman" (along with sister Maggie); in "", a 1994 episode of ""; and in the 1998 comedy "Homegrown". Along with their mother, Jake and Maggie appeared in two episodes of "Molto Mario", an Italian cooking show on the Food Network. Prior to his senior year in high school, the