Craig Chester was born in West Covina, California, the son of Cecil, lead singer in the rock band "Whiskey" and Linda, a homemaker. He moved with his family to Carrollton, Texas at the age of twelve when his father accepted a corporate job with Nestlé. At age fifteen, Chester was diagnosed with the congenital facial deformity Long face syndrome. The condition's most striking symptom is an excessively long lower face height. At eighteen, Chester spent a year undergoing multiple reconstructive surgeries. Chester moved to New York City in 1985, with a new face, to study at The American Academy of Dramatic Arts. Following graduation, he performed in various stage productions in New York, including a play written by Joanne Woodward who, upon noticing his naturalistic acting style, encouraged Chester 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 which earned Chester an Independent Spirit Award nomination for Best Actor. Janet Maslin of The New York Times described the film as "dazzling". Peter Travers of Rolling Stone described Swoon as "a great film...haunting and visionary". Chester went on to act in a string of critically acclaimed independent films. He was openly gay from the inception of his career, rare at that time.
Chester transitioned out of acting and into writing.
