Holloway's ambition for acting led him to Los Angeles, where he landed a role in the comedy Doctor Benny. He followed up with lead roles in movies Mi amigo, Moving August and Cold Heart. Following these roles, he gained recognition for his lead role in the Sci-Fi Channel movie Sabretooth with David Keith and John Rhys-Davies. He also made appearances in Good Girls Don't episode "Addicted to love", NCIS episode "My other left foot",The Lyon's Den episode "Separation Anxiety",Walker, Texas Ranger episode "Medieval Crimes", CSI: Crime Scene Investigation episode "Assume Nothing", and Angel episode "City of" .Holloway appeared in the Aerosmith video for the song "Cryin'" as a thief who tries to steal Alicia Silverstone's purse from a diner. In the video, she catches him and beats him up.

Holloway is best known for his role as James "Sawyer" Ford in the hit television series Lost. The show propelled Holloway to celebrity status, but left him with little time to leverage his fame wi