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 he portrayed a young man from West Virginia striving to win a science scholarship to avoid becoming a coal miner. The film earned $32 million and was described in the "Sacramento News and Review" as Gyllenhaal's "breakout performance". "Donnie Darko", Gyllenhaal's second film, was not a box office success upon its initial 2001 release but eventually became a cult favorite. Directed by Richard Kelly, the film is set in 1988 and stars Gyllenhaal as a troubled teenager who experiences visions of a tall rabbit named Frank who tells him that the world is coming to an end. Gyllenhaal's performance was