Massey has a history in entertainment of being an actor, comedian and also as a talk show host. In the past, she was lead host of the nationally syndicated radio talk show "Radio Girls" and was on 97.1 KLSK FM talk radio station in Los Angeles, as co-host of "Lauren & Gretchen Uncut." Massey had a love of the theatre and performing from an early age, and attended Dallas's Booker T. Washington High School for the Performing and Visual Arts. This love evolved into a long journey of writing and performing through many cities with various theater companies, improvisational theatre groups and then as a stand-up comedian later in her life. She is well known for being one of the various presenters on the Playboy TV television show, Sexcetera.