Born in the vibrant city of Los Angeles, Rolston's journey in photography began with a serendipitous discovery by the renowned artist Andy Warhol, who introduced him to the world of celebrity-focused Interview magazine. This successful career pivot led to a string of high-profile assignments, including shooting covers and editorial spreads for the esteemed publications of Jann Wenner's Rolling Stone, as well as Harper's Bazaar, Vogue, Vanity Fair, W, GQ, Esquire, Cosmopolitan, O, The Oprah Magazine, and The New York Times.
As Rolston's creative vision expanded beyond the realm of still photography, he began to conceive, write, and direct music videos and television commercials for a diverse array of clients, including the likes of Madonna, Janet Jackson, Christina Aguilera, Beyoncé, L'Oreal, Revlon, Estee Lauder, Clairol, Levi's, Pantene, Elizabeth Arden, Gap, and Polo Ralph Lauren, among others.
In addition to his work in the world of beauty and fashion, Rolston has also made appearances as a guest expert on a range of beauty-oriented broadcast programs, including Bravo's Shear Genius and Make Me a Supermodel, as well as the CW's America's Next Top Model. Furthermore, he has taken on the role of Creative Director, working in the fields of experiential design, hospitality, product design, and new media ventures.