Hollywood worked as a swimsuit, catalogue, glamour, and calendar model prior to her porn career. While working as a model, an agent booked her for a masturbation scene. She was deceived into believing it was going to be a photo shoot, but decided to shoot the scene regardless. She initially worked only in solo, glamour, and girl/girl scenes. She started doing sex scenes with men a year and a half after debuting in porn. Ash is short for Ashley, which is her real first name, and Hollywood was her nickname before she began working in porn.
Hollywood hosts a show called Tap That Ash on Vivid Radio. She also has a podcast titled Ashaholics.