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 and lasts for 20 years. The film was often referred to in the media with the shorthand phrase "the gay cowboy movie", though there was differing opinion on the sexual orientation of the characters. The film won the Golden Lion prize at the Venice Film Festival. The film went on to win four Golden Globe Awards, four British Academy of Film and Television Arts (BAFTA) Awards, and three Academy Awards. Gyllenhaal was nominated for an Academy Award in the category of Best Supporting Actor for his performance but lost to George Clooney for "Syriana". Gyllenhaal also won the Best Supporting