Harold Crick
Harold Crick is the main character of the film, as well as the hapless protagonist in the novel that Karen Eiffel is writing. At the start of the film, Harold is exceedingly precise and calculating, brushing his teeth a certain number of times and being especially precise about time. The introduction of a narrator into his life changes his outlook, and with his death in sight, he begins to go after what he wants and becomes less formal. He stops being so precise about time, buys a guitar (a lifelong dream), and falls in love with a beautiful woman. By the end of the film, Harold has gone from ineffective office cog to local hero, living up to the protagonist status that Karen has given him.
Ana Pascal
Ana is a politically progressive baker who has evaded paying her taxes. Since Harold works for the Internal Revenue Service, he is sent to audit her at the start of the film, and is instantly attracted to her. Initially, she sees him as a no-good taxman, and feels antagonistic towards him. Ana is idealistic and giving, generously sharing her baked goods with the members of her community and wanting to make the world a better place through cookies.
Karen Eiffel
Karen is a profound and well-known author, known best for killing the main characters of her books in compellingly tragic ways. She is reclusive and eccentric, exceedingly difficult to track down. A consummate artist, she is often putting herself in drastic situations, imagining death, in order to write realistically and compellingly about her characters.
Professor Jules Hilbert
Hilbert is a literature professor who helps Harold put together the clues to discover what exactly is happening to him. He is a longtime fan of Karen Eiffel's, and has sent her a great deal of mail to which she has never responded. He is also the lifeguard at the faculty pool at his university.
Penny Escher
Penny is hired by Karen's publisher to keep an eye on her and make sure that she finishes her manuscript, as she has recently been suffering from writers' block. In contrast to Karen, Penny is very pragmatic and helpful, thinking about the practicals of the creative process, while Karen remains preoccupied with the more torturous and edgy elements. In the end, Karen is grateful for Penny's help.
Dave
Dave is Harold's only friend, who works for the I.R.S. with him. When Harold's apartment gets demolished, Dave lets Harold stay with him. Dave's biggest dream is to go to Space Camp.