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.
Marilyn Monroe Sings “Happy Birthday” to JFK, May 19, 1962:
I was on assignment for LIFE at the old Madison Square Garden that night — one of many photographers down in front of the stage. The police, with directions from the Secret Service, were forcing the press into a tight group behind a rope. I knew that all the “rope-a-dopes” would get the same shot, and that would not work for LIFE. I squeezed between the cops and took off looking for a better place.
It seemed that I climbed forever. When I found a pipe railing to rest the lens on (exposure was strictly by guess), I could see JFK through the telephoto. When the moment came, the Garden went black. Total silence.
One spotlight snapped on, and there was Marilyn, in that dress, crystals sparkling and flashing. She was smiling, with everyone on the edge of their seats. Then, in her breathy, sexy, unique voice, looking the entire time right at JFK, she sang.
In two-and-a-half months, Marilyn would be dead. In eighteen months, Kennedy would be assassinated; Vietnam would turn into our worst nightmare; Camelot would be gone. But that night, Marilyn’s brief song stopped the world.
Brigitte Bardot Throws a Tantrum on the Set of Shalako, Spain, 1968:
I rode with Bardot to the set many times in her white Rolls-Royce. On one of those mornings, B.B. saw a stray, starving dog and ordered her driver to stop. It was love at first sight. The starving mutt loved B.B. and the Rolls, and B.B. loved the mutt. B.B. put all her retainers on the case. She would make a perfect life for this “adorable” dog.
Her hairdresser bathed the dog. Her chauffeur tore off in the Rolls for filet mignon. The dog never left her side until the fourth day — when he keeled over dead from too much of the good life.
B.B. started to cry and worked herself up to uncontrollable wailing. She locked her dressing room door. Cast and crew [including co-star Sean Connery] were standing by. Lunch time came and went. The wailing went on and on. The whole day was lost; mucho dinero.
Woody Allen in Vegas, 1966:
It was a pivotal year for Woody. He published stories in the New Yorker, wrote and directed his first film, What’s Up Tiger Lily? and had a Broadway hit, Don’t Drink the Water. He was on fire, and LIFE wanted to celebrate him with a cover story. I was given the job of shooting Woody in Las Vegas, along with any other photos I could get of his other activities.
The Woody I met at Caesars Palace was one of the quietest, most cooperative people I’ve ever worked with. The only problem was that he didn’t do anything except stay in his room, write, and practice his clarinet until it was time for his standup routine. Then I remembered the kitschy nude Roman statues in front of Caesars. With trepidation, I asked Woody if he would pose with one of the nudes. He thought it was a funny idea and said “sure.” That was a relief and I pressed my luck, asking him if he would wear a red sweater that I happened to have with me.
“Is it cashmere?” he asked. It wasn’t; it was wool.
Woody said he was allergic to wool, but after some pleading, he agreed to wear it.
I needed the contrast with the white statue, and a bit of red never hurt for a cover shoot. The statue seemed to inspire Woody, and he really came to life. He hugged and vamped and swung around. It was tremendous fun.
Phone calls and telexes from New York assured me the shots were great and would run with the story.
But LIFE was a weekly and would use a news cover whenever they could. Unfortunately for me, some damn thing happened that week and LIFE scrapped the Woody Allen cover. It was heartbreaking — but I still had the great thrill of working with one on the comic geniuses of my time.
— Ben Cosgrove is the Editor of LIFE.com