Douglas is a filmmaker and plyawright. For the theatre he wrote the book for the Carole King musical, Beautiful, and the play, Checkers, which opened the 30th anniversary season at New York's Vineyard Theatre. He collaborated with Woody Allen on the screenplay for Bullets Over Broadway, for which they were nominated for an Academy Award. His first film as writer/director was his adaptation of Jane Austen's Emma. He also directed and wrote the adaptation of Nicholas Nickleby, which won the Best Ensemble Cast from the National Board of Review, as well as Company Man, Infamous and His Way.