Reagan is known for her red hair, freckled face and puffy nipples, and is represented by the A List Talent agency. Her first interracial scene was with Jack Napier in the 2007 film The Gauntlet 3. In the same film she also had sex with 23 men, and performed her first creampie scene. She does not perform anal sex on screen. In May 2008 she featured as one of Adult Video News' four "Fresh New Faces" cover girls. She appeared at the 12th annual Erotic LA convention at the Los Angeles Convention Center in June 2008. Reagan has been engaged to fellow pornographic actor Dane Cross, whom she works with on a regular basis, since 2007. She appeared in a print ad for American Apparel in October 2008, credited as "Jillian".