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While still a student at Art Center, Rolston was "discovered" by Andy Warhol, for Warhol's celebrity focused Interview magazine, where he began a successful career in photography. Soon after, Rolston began shooting covers and editorial assignments for founding editor Jann Wenner of Rolling Stone, as well as for other publications such as Harper’s Bazaar, Vogue, Vanity Fair, W, GQ, Esquire, Cosmopolitan, O: The Oprah Magazine and The New York Times. Rolston has completed thousands of photoshoots in his career, including over 100 covers for Rolling Stone alone.

Four monographs have been published of Rolston’s work: Big Pictures, A Book of Photographs (1991), a collection of early work with an introduction by Tim Burton, published by Bullfinch Press, New York; beautyLIGHT, Pictures at a Magazine (2008), a survey of twenty years of Rolston’s celebrity portrait photographs, published by teNeues, Germany; Talking Heads: The Vent Haven Portraits (2012), a fine art project composed of monumental portraits of ventriloquial figures, published by Pointed Leaf Press, New York; and Hollywood Royale: Out of the School of Los Angeles (2017), a mid-career retrospective, published by teNeues, Germany.

Rolston also conceives, writes and directs film projects, having directed over 100 music videos and 200 television commercials in his career, including collaborations with artists as diverse as Madonna, Janet Jackson, Beyoncé Knowles, Miley Cyrus and Marilyn Manson, as well as numerous advertising campaigns - both print and television - for clients such as L’Oreal, Revlon, Estée Lauder, Clairol, Levi's, Pantene, Elizabeth Arden, Gap and Polo Ralph Lauren, among others.

Rolston’s original short film The Most Beautiful Woman in the World (2011, color, 3:00 min) was screened as part of SF Shorts: The San Francisco International Festival of Short Films (2013). The Whitney Museum of American Art screened "Whatta Man" (1994, color, 4:52 min) as part of its Through the Lens of the Blues Aesthetic: An Evening of Short Films Selected by Kevin Everson (April, 2013). Other films include "Foolish Games" for musical artist Jewel (1997, color, 3:57 min), which received a nomination for Most Stylish Music Video at the 1997 VH1 Vogue Fashion Awards; "Be Without You" for musical artist Mary J. Blige (2005, color, 4:09 min), which received a nomination as Best R&B Video (MTV Video Music Awards, 2006); and "Candyman" for Christina Aguilera (2007, color, 3:18 min) for which Rolston was nominated for Best Director (MTV Video Music Awards, 2007).

Since its inception, R-ROLL has produced projects for clients including Time, Inc., Amazon.com, ESPN and A&E/Lifetime Networks, among others. Said Rolston, “We’re now entering an era where the ‘making of’ is just as important as the ‘of’. And clients seem to enjoy the integration of our media services. Print, film, design, documentary, you might say we’re a ‘one-stop-shop'.”

As Rolston began to redefine the scope of his career, he expanded his practice into the fields of creative direction and branding, developing innovative projects in the area of experiential design, including hospitality projects, product design and new media ventures. Rolston’s first hospitality brand creation, developed for Los Angeles-based hotel and restaurant owner Sam Nazarian's company sbe Entertainment, opened in 2010. Called The Redbury, Rolston was deeply involved in every aspect of the project, from the naming to the logo, from design concepts to marketing strategies. As the brand's creative director, he oversaw every detail with an extensive team that included architects, interior designers, graphic designers, music supervisors, scent experts, the uniform company that created the staff wardrobe, and more. Since that time, other hospitality clients have included Mahmood Khimji's Highgate, Richard Branson's Virgin Hotels, and Barry Sternlicht's SH Hotels and Resorts.

Vanitas: The Palermo Portraits is yet another dramatically-scaled portrait series, this depicting Christian mummies housed in the Capuchin Catacombs of Sicily. The project, which has not yet been published or exhibited, represents Rolston’s continuing evolution as a photographer and is an attempt to elevate his portraiture to a conceptual level.

Responding to client needs, Rolston established a production unit he calls ‘R-ROLL’. Its mission is to provide his clients with behind-the-scenes documentaries of his photo, film and creative direction assignments. According to Rolston, “there’s an overwhelming demand for filmed content, as clients expand their reach beyond traditional media.” R-ROLL was created to serve Rolston’s usual mix of editorial, advertising, entertainment and hospitality clients. “I decided to call it R-ROLL as a joke on ‘B-roll’ (industry parlance for behind-the-scenes footage). The ‘R’ is for ‘Rolston'.”

Hollywood Royale: Out of the School of Los Angeles — which includes Rolston’s fourth monograph, as well as a traveling exhibition — is a retrospective of his editorial portraits from 1977 to 1993. Edited by long-time Los Angeles–based gallerist and curator David Fahey, this series presents an array of portraits that capture the 1980s and its myriad talents. From Michael Jackson and Madonna, to Prince, George Michael and Cyndi Lauper, the selection of images reflects the era.

Born in Los Angeles, Rolston studied drawing and painting in his home town at the Chouinard Art Institute and Otis College of Art & Design, as well as in the Bay Area at the San Francisco Art Institute. He also studied illustration, photography, imaging and film at Art Center College of Design in Pasadena, California, where in 2006, he received an Honorary Doctorate.