To say that Los Angeles native Matthew Rolston broke into the photography business “rapidly” would hardly be sufficient. “My very first client was Andy Warhol for Interview magazine,” he recalls. “My second client was Harper’s Bazaar. My third client was Michael Jackson.” He then rethinks this. “Actually, my third client was Jann Wenner, for Rolling Stone,” he clarifies.

Rolston had crossed paths with Warhol socially at the artist’s nightclub the Factory in New York, but the opportunity at Warhol’s Interview came when a stylist friend from Art Center College of Design in Pasadena — where Rolston studied photography then, and teaches courses now — called about a last-minute job. “And lo and behold, I got my first assignment for a magazine.” Rolston says, “And it was to shoot Steven Spielberg.”

This story first appeared in the November 18, 2015 issue of WWD. Subscribe Today.

Photographing Harrison Ford and a then-unknown “Star Wars” cast followed — as did a plethora of covers, and a fashion-forward shoot with Jackson. (Later, Rolston would be the last to photograph the pop icon, for his “Thriller” relaunch, in 2007.) “I actually dressed him in some of my own clothes,” recalls Rolston, who bought an embroidered crest with a crown and the letter “J” from an “English-y” Beverly Hills men’s store, and had it sewn onto a cardigan. “And he started this whole craze that I ended up calling ‘Hollywood Royale.’ It sort of indicated the idea of royalty — that he was the King of Pop.” Only, this was prior to Jackson ever being called such.

“So I had some kind of intuition for how to image people, in a time when there weren’t so many people doing that,” says Rolston, who’s renowned for his deftness with lighting, and ability to key into his subjects. His glitzy roster includes A-listers from Beyoncé to Angelina Jolie to Oprah, with whom he’s collaborated on some 40 covers.

He got his first glimpse of Hollywood glamour through black-and-white photos of MGM stars — by classic Forties photographers like George Hurrell — that decorated his grandfather’s medical office. “I was absolutely fascinated by the quality of the skin and the way those photographers elevated the stars to this iconic status,” says the lensman, now credited for doing the same.

Rolston’s creative skillset naturally lent itself to commercials (for brands like Gap and Polo Ralph Lauren) and music videos (he’s directed “at least 100” for artists from Janet Jackson to Madonna), and most recently, to hospitality. He served as creative director for SBE’s music-centric Redbury Hotel in Hollywood, and is currently conceptualizing a $150 million project in San Francisco. On the fine arts front, Rolston’s “Talking Heads: The Vent Haven Portraits” examined the power of projecting onto subjects in photographs of ventriloquists’ dummies, and a new project explores Hollywood’s denial of death and aging through photos of preserved Christian mummies in Palermo, Italy.

“As my career has grown and gone on, I’ve never really abandoned anything,” Rolston says. “It’s more like a flowering, or a tree just getting more branches of leaves: It kind of keeps on expanding.”

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