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Whether he was shooting as a staff photographer for LIFE or freelancing for other major publications — Smithsonian, Fortune, Newsweek — Bill Ray never shied from an assignment, however large or (seemingly) small, during the course of his long career. Global events and quiet moments; armed conflicts and avant-garde artists; the grit and menace of the early Hells Angels and the bracing glamor of the Camelot years, he covered it all.
“I threw myself, one hundred percent, into every shoot,” Ray says today. “And I loved it.”
For this Photographer Spotlight, however, LIFE.com chose to focus not on the dizzying variety that, in part, defines Ray’s portfolio, but on his tremendous work in one particular mode: namely, celebrity portraits.
Even a partial roll call of the men and women Bill Ray photographed for LIFE reads like a Who’s Who of Sixties pop culture: Marilyn Monroe, Sinatra, the Beatles, Natalie Wood, Liz Taylor, Elvis, Steve McQueen, Jackie Kennedy and on and on and on. But even more remarkable than the number of genuine legends Ray covered is that he managed to capture something utterly distinctive about each and every one.
It’s difficult to imagine one photographer capable of showing us something elemental about personalities as wildly disparate as, say, Brigitte Bardot, Sonny Liston and Woody Allen — but Bill Ray did just that, again and again.
Some photo captions in this gallery include Ray’s memories of what it was like to photograph these people. But we’ve also included, below, a few of the longer — and often hilarious — stories Bill Ray tells about documenting the lives and careers of the 20th century’s most famous public figures.
— Ben Cosgrove is the Editor of LIFE.com