Holloway was born in San Jose, California, the second of four boys of a nurse mother and a surveyor father. His family moved to the Blue Ridge Mountains of Georgia when he was two. He was raised in Free Home, Georgia. Holloway is related to Baptist preacher Dr. Dale Holloway and author and World War II prisoner of war Carl Holloway. He is also a descendant of Robert E. Lee. Holloway attended Cherokee High School in Canton, Georgia, graduating in 1987. He developed an interest in movies at a very young age. He studied at the University of Georgia but left after one quarter due to financial constraints.