Written By: Liz Ronk

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 said. “And I loved it.”

For this Photographer Spotlight, however, LIFE.com focussed on one aspect of Ray’s varied portfolio: celebrity portraits.

Even a partial roll call of the stars Bill Ray photographed for LIFE reads like a Who’s Who of Sixties pop culture: Marilyn Monroe, Sinatra, the Beatles, Natalie Wood, Elizabeth Taylor, Elvis, Steve McQueen, Jackie Kennedy and on and on and on. What’s truly remarkable is that he managed to capture something utterly distinctive about each 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 told about documenting the lives and careers of the 20th century’s most famous public figures.

[Buy Bill Ray’s My LIFE in Photography, from which some of these memories, slightly edited, are taken.]

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.

Private Elvis Presley in Brooklyn in 1958, before leaving the States to serve in the Army in Germany.

Pvt. Elvis Presley in Brooklyn, 1958, before leaving the States to serve in Germany.

Bill RayThe LIFE Picture Collection © Meredith Corporation

Gina Lollobrigida signs autographs in front of New York's old Metropolitan Opera House, 1958.

Gina Lollobrigida signed autographs in front of New York’s old Metropolitan Opera House, 1958.

Bill Ray

Frank Sinatra on the set of the movie, "Can-Can," 1959.

Frank Sinatra on the set of the movie, “Can-Can,” 1959.

Bill Ray

Elizabeth Taylor at a Hollywood luncheon to mark Soviet Premier Nikita Khrushchev's historic visit to the U.S., 1959.

Elizabeth Taylor 1959

Bill Ray

Legendary saloonkeeper Toots Shor (right) with John Wayne on closing night at Shor's famous New York watering hole, 1959.

John Wayne, Toots Shor, 1959

Bill Ray

Jackie Kennedy in Hyannisport, 1960.

Jackie Kennedy 1960

Bill Ray

Ella Fitzgerald at the old Madison Square Garden in New York on the night Marilyn sang to JFK, May 1962.

Ella Fitzgerald 1962

Bill Ray

Marilyn Monroe sings "Happy Birthday" to JFK, New York City, May 19, 1962.

Marilyn Monroe 1962

Bill Ray

Heavyweight champ Sonny Liston glares at Floyd Patterson during the weigh-in for their second title bout in two years, Las Vegas, July 1963. The fight lasted a little more than two minutes, with Liston flooring Patterson three times in the first round.

Sonny Liston, Floyd Patterson, 1963

Bill Ray

Natalie Wood, 1963.

Natalie Wood 1963

Bill Ray

Jill St. John, 1963.

Jill St. John 1963

Bill Ray

Marlon Brando and Paul Newman supporting a sit-in for fair housing, Sacramento, Calif., 1963.

Marlon Brando and Paul Newman 1963

Bill Ray

The great Austrian actress Senta Berger, 1964.

Senta Berger 1964

Bill Ray Time & Life Pictures/Shutterstock

The Beatles arrive in Los Angeles in August 1964.

The Beatles 1964

Bill Ray Time & Life Pictures/Shutterstock

Woody Allen, Las Vegas, 1966.

Woody Allen 1966

Bill Ray

Michael Caine, 1966.

Michael Caine 1966

Bill Ray Time & Life Pictures/Shutterstock

Ray Charles at Carnegie Hall, 1966

Ray Charles performed at Carnegie Hall, 1966.

Bill Ray/The LIFE Picture Collection © Meredith Corporation

Nancy Sinatra, 1966.

Nancy Sinatra 1966

Bill Ray Time & Life Pictures/Shutterstock

Faye Dunaway and Steve McQueen on the set of The Thomas Crown Affair, 1967.

Faye Dunaway and Steve McQueen 1967

Bill Ray Time & Life Pictures/Shutterstock

Lew Alcindor 1967

Bill Ray Time & Life Pictures/Shutterstock

Brigitte Bardot in Spain on the set of Edward Dmytryk's run-of-the-mill adventure-romance, Shalako, 1968.

Brigitte Bardot 1968

Bill Ray

Sharon Tate and Roman Polanski, London, 1968.

Sharon Tate and Roman Polanski 1968

Bill Ray Time & Life Pictures/Shutterstock

Jane Fonda and daughter Vanessa, 1971.

Jane Fonda and daughter 1971

Bill Ray Time & Life Pictures/Shutterstock

George Harrison and Bob Dylan at the Concert for Bangladesh in New York, 1971.

Bill Ray/The LIFE Picture Collection © Meredith Corporation

Ann-Margaret, 1972.

Ann Margaret 1972

Bill Ray

David Frost and Diahann Carroll (who were once engaged, but never married) watch themselves as they appear on two different talk shows, 1972.

Diahann Carroll and David Frost

Bill Ray Time & Life Pictures/Shutterstock

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