He began his acting career at a young age in the 1997 film As Good as It Gets, a role for which he won the Hollywood Reporter Young Star award. His acting career continued, with several other high profile films, including his role in the 2001 Johnny Depp film Blow, as the child version of Depp's character, and Pearl Harbor, in which he played the young version of Ben Affleck's character. Possessing an impressive resume as a child actor, he has continued to act as a teen/adult, achieving underground critical acclaim for his performance in the 2004 film The Butterfly Effect as the young Tommy Miller. He also acted in The Amityville Horror alongside Ryan Reynolds and Melissa George. Lately, he has appeared as a guest star in several TV shows, such as Life and In Plain Sight, and has become involved in the independent film community with projects such as Exodus Fall and Hickory Nation.
In 2008 James starred in, and was an executive producer for the short film Manifest Destiny.