Craig Chester was born in West Covina, California, to Cecil Chester, the lead singer of the rock band "Whiskey", and Linda Chester, a homemaker. When he was twelve years old, his family relocated to Carrollton, Texas, after his father accepted a corporate job with Nestlé.
As a teenager, Chester faced a significant challenge when he was diagnosed with Long face syndrome, a congenital facial deformity characterized by an excessively long lower face height. At the age of fifteen, he underwent multiple reconstructive surgeries, which lasted for a year.
Following his recovery, Chester moved to New York City in 1985 to study at The American Academy of Dramatic Arts. After graduating, he performed in various stage productions in New York, including a play written by Joanne Woodward, who noticed his naturalistic acting style and encouraged him to pursue a career in film.
Chester's acting debut was in the feature film Swoon, a contemporary re-telling of the infamous Leopold & Loeb murder of Bobby Franks. His performance earned him an Independent Spirit Award nomination for Best Actor. The film received widespread critical acclaim, with Janet Maslin of The New York Times describing it as "dazzling" and Peter Travers of Rolling Stone calling it "a great film...haunting and visionary".
Throughout his acting career, Chester was openly gay, which was rare at the time. He went on to act in a string of critically acclaimed independent films.
Eventually, Chester transitioned out of acting and into writing.
