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 and The New York Times Magazine.

[8] Rolston's images have been exhibited at institutions and museums in solo and group shows including Beauty CULTure (with Lauren Greenfield, Herb Ritts, Andres Serrano, and Carrie Mae Weems, 2011),[9] The Annenberg Space for Photography, Los Angeles, California; The Warhol Look: Glamour, Style, Fashion (curated by Mark Francis and Margery King),[10] The Whitney Museum of American Art, New York (1997); and Fashion and Surrealism, FIT Gallery, New York, 1987 (traveled to the Victoria & Albert Museum, London, UK, 1988).

[16] Rolston has also conceived, written and directed numerous film projects, having overseen over 100 music videos and 200 television commercials in his career, including collaborations with artists as diverse as Madonna, Janet Jackson, Beyoncé Knowles, and Miley Cyrus, 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.

[17] Rolston established a documentary production unit called ‘R-ROLL’, a verbal play on industry reference to ‘B-roll’, that is – the capturing of behind-the-scenes footage.

"[18] Rolston has appeared as a guest expert on a spectrum of beauty-oriented broadcast programs, from Bravo's Shear Genius and Make Me a Supermodel to the CW's America's Next Top Model.

[24] With a 2024 project, The Portal: An Art Experience by Jewel, Rolston expanded his creative direction practice into the museum world.

[25] This hologram, positioned in the atrium lobby of the museum, acted as the centerpiece of an immersive installation, greeting visitors to the site.

[26] Rolston has created four photographic fine art projects that have led to a series of publications and exhibitions: Talking Heads: The Vent Haven Portraits consists of monumentally scaled color portraits of ventriloquial figures housed in the Vent Haven Museum in Fort Mitchell, Kentucky.

Hollywood Royale: Out of the School of Los Angeles – which includes Rolston's fourth monograph, as well as a travelling exhibition – is a retrospective of his editorial portraits from 1977 to 1993.

[30][31] 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.

[38] The project is, according to Rolston "a meditation on mortality";[39] it represents the artist's continuing evolution as a photographer and is an attempt to elevate his portraiture to a conceptual level.

[45] Rolston's classes are situated within ArtCenter's film program, however they invite members from diverse disciplines including advertising and creative direction, photography and imaging, fine art, and other courses of study offered at the college.

This fund is devoted to supporting students in product and fashion design, with an emphasis on communication and creative direction skills.