Holloman is the youngest child in her family. She has two older brothers. She graduated from Saint Mary's School, an Episcopal boarding school for girls in Raleigh, in 1986. She attended the University of North Carolina where she graduated with a degree in Performance Communication. She appeared in numerous theater productions in Chapel Hill and Raleigh, as well as in Chicago and London. She studied painting and sculpting at UCLA and at The San Francisco Art Institute.
After graduating from UNC, Holloman moved to Chicago to work with the Piven Theatre Workshop. She studied with John Lynn in Los Angeles, and was cast in David Orr's independent feature Blossom Time. She moved to New York City in early 1994 and appeared in stage productions such as Tennessee Williams' The Glass Menagerie, Carson McCullers' The Heart Is a Lonely Hunter at the Theatre for the New City. Holloman also performed off-Broadway in Julia Jordan's Night Swim at Playwright's Horizons.
In 1995, Holloman began her film career with her role as Randy Dean in The Incredibly True Adventure of Two Girls in Love. She worked steadily in a variety of mostly independent film roles, such as The Myth of Fingerprints, Boogie Nights and Tumbleweeds.