In 1999, Murray moved to Hollywood where he supported himself modeling for such clients as Skechers, Tommy Hilfiger and Gucci. Then he was cast in the role of rich brat, Tristin DuGray on Gilmore Girls; which was one of the main characters in the first season of the series and then became a recurring character thereafter. He appeared in several guest starring television roles, including an episode of Undressed and an episode of Diagnosis: Murder. Murray portrayed the role Charlie Todd on the successful television series Dawson's Creek in 2001. In 2003, he appeared in television film, Aftermath: A Long Way Home. Murray then appeared in the Walt Disney Pictures feature film, Freaky Friday alongside Lindsay Lohan and Jamie Lee Curtis. The film was a major box office success, earning a total of $110,222,438 in the United States alone. Critics were mostly positive in their reviews of the film, and the film garnered a "B" grade on Yahoo! Movies and an 88% "Certified Fresh" approval rating on Rotten Tomatoes. Murray also appeared in the television film The Lone Ranger where he portrayed the role of Luke Hartman.