Written By: Ben Cosgrove

As a boy, Allan Grant dreamed of becoming an aeronautical engineer. When his career path took a different route, the flying industry’s loss became the photography world’s and, specifically, LIFE magazine’s gain.

If any photographer ever captured the lighter side of show business, it was the confident New York native who, as a teen, traded a model airplane that he’d built for a pocket Kodak camera, and never looked back.

A LIFE staffer from 1947 until the late 1960s, Grant covered the entertainment world from the inside. His unique blend of cool appraisal and obvious affection for (most) of his subjects went a long way toward making the stars seem just as quirky and approachable as the rest of us mortals.

But he was hardly a sycophantic “celebrity photographer,” and Grant (1919 – 2008) was perfectly aware of his own skills as a photographer, and a newsman. When asked in an early 1990s interview by another long-time LIFE staffer, John Loengard, what kind of photographer he thought he was, Grant replied with a refreshing directness: “I would say a good one, for starters. I stayed [at LIFE] for a long time. I was very versatile; I did everything.”

That he did. While particularly known for his winning portraits of showbiz royalty as the pictures in this gallery demonstrate when called upon Grant was a perfectly adept chronicler of harder news. His portraits of Marina Oswald made shortly after her husband shot President Kennedy, for example, captured a personal side of that epic, era-defining story that few other media outlets could touch. His pictures of atomic tests and, especially, their aftermath in the early 1950s managed to add a human dimension to an issue that frequently felt, by turns, too clinical and too terrifying for the average citizen to grasp.

But it was, in the end, Grant’s portraits of the stars of the Fifties’ and Sixties’ that showed his real ability to get close to people, and capture something genuine, if fleeting, about the rich and famous in their unguarded moments. Shortly after Grant died in 2008, Dick Stolley, who was LIFE’s Los Angeles bureau chief in the early ’60s and later served as the magazine’s managing editor, pointed out in a statement that Allan Grant was “very handsome and glamorous, two virtues that made him popular in Hollywood.”

Handsome, glamorous and supremely talented. Some guys have all the luck.

Liz Ronk edited this gallery for LIFE.com. Follow her on Twitter at @LizabethRonk.

Audrey Hepburn and Grace Kelly wait backstage at the RKO Pantages Theatre during the 28th Annual Academy Awards, 1956.

Audrey Hepburn and Grace Kelly waited backstage at the RKO Pantages Theatre during the 28th Annual Academy Awards, 1956.

Allan Grant The LIFE Picture Collection/Getty Images

Audrey Hepburn, 1956.

Audrey Hepburn, 1956.

Allan Grant The LIFE Picture Collection/Getty Images

Senator Richard Nixon on the roof of his home in Los Angeles, trying to douse fires caused by a brush blaze, 1961.

Senator Richard Nixon stood on the roof of his home in Los Angeles, trying to douse fires caused by a brush blaze, 1961.

Allan Grant The LIFE Picture Collection/Getty Images

Dean Martin reads lines with Shirley MacLaine, 1958.

Dean Martin read lines with Shirley MacLaine, 1958.

Allan Grant The LIFE Picture Collection/Getty Images

Dean Martin relaxes with his sons at home, 1958.

Dean Martin relaxed with his sons at home, 1958.

Allan Grant The LIFE Picture Collection/Getty Images

Angie Dickinson, 1958

Angie Dickinson on set of Rio Bravo, 1958.

Allan Grant The LIFE Picture Collection/Getty Images

Kirk Douglas, 1949.

Kirk Douglas, 1949.

Allan Grant The LIFE Picture Collection/Getty Images

Groucho Marx in rehearsal, 1960.

Groucho Marx in rehearsal, 1960.

Allan Grant The LIFE Picture Collection/Getty Images

Chico and Harpo Marx, 1959.

Chico and Harpo Marx, 1959.

Allan Grant The LIFE Picture Collection/Getty Images

Harpo Marx, 1948.

Harpo Marx, 1948.

Allan Grant The LIFE Picture Collection/Getty Images

George Burns and his wife, Gracie Allen, 1958.

George Burns and his wife, Gracie Allen, 1958.

Allan Grant The LIFE Picture Collection/Getty Images

Paul Newman, 1955

Paul Newman had make-up removed on the set of The Battler (TV play), 1955.

Allan Grant The LIFE Picture Collection/Getty Images

Buster Keaton and Donald O'Connor rehearse for a movie based on Keaton's life, 1956.

Buster Keaton and Donald O’Connor rehearsed for a movie based on Keaton’s life, 1956.

Allan Grant The LIFE Picture Collection/Getty Images

Cecil B. DeMille, Billy Wilder and Gloria Swanson

Cecil B. DeMille, Billy Wilder and Gloria Swanson during the filming of Sunset Boulevard, 1949.

Allan Grant The LIFE Picture Collection/Getty Images

James Dean, 1956

James Dean on location for the movie Giant, 1956.

Allan Grant The LIFE Picture Collection/Getty Images

Bob Hope, 1962.

Bob Hope, 1962.

Allan Grant The LIFE Picture Collection/Getty Images

Elizabeth Taylor, 1961

Elizabeth Taylor at a party after winning the Oscar for her performance in BUtterfield 8, 1961.

Allan Grant The LIFE Picture Collection/Getty Images

Natalie Wood and Warren Beatty at the Academy Awards, 1962.

Natalie Wood and Warren Beatty at the Academy Awards, 1962.

Allan Grant The LIFE Picture Collection/Getty Images

Audrey Hepburn and Grace Kelly backstage at the RKO Pantages Theatre during the 28th Annual Academy Awards, 1956.

Audrey Hepburn and Grace Kelly backstage at the RKO Pantages Theatre during the 28th Annual Academy Awards, 1956.

Allan Grant The LIFE Picture Collection/Getty Images

Dorothy Dandridge at home, 1954.

Dorothy Dandridge at home, 1954

Allan Grant The LIFE Picture Collection/Getty Images

Dizzy Gillespie during a jam session, 1948.

Dizzy Gillespie during a jam session, 1948

Allan Grant The LIFE Picture Collection/Getty Images

Bob Hope (right) and Frank Sinatra rehearse for The Bob Hope Show, 1962.

Bob Hope (right) and Frank Sinatra rehearsing for The Bob Hope Show, 1962.

Allan Grant The LIFE Picture Collection/Getty Images

Sammy Davis Sr., Sammy Davis Jr. and Will Mastin on stage at Ciro's in West Hollywood, 1955.

Sammy Davis Sr., Sammy Davis Jr. and Will Mastin on stage at Ciro’s in West Hollywood, 1955.

Allan Grant The LIFE Picture Collection/Getty Images

Bobby Darin in his dressing room, 1959.

Bobby Darin in his dressing room, 1959.

Allan Grant The LIFE Picture Collection/Getty Images

Ella Fitzgerald, 1958.

Ella Fitzgerald, 1958.

Allan Grant The LIFE Picture Collection/Getty Images

Actress-model Suzy Parker, 1957.

Actress-model Suzy Parker, 1957.

Allan Grant The LIFE Picture Collection/Getty Images

Edith Piaf caught in a montage of expressions and gestures while singing during her performance at New York's Versailles nightclub, 1952.

Edith Piaf was caught in a montage of expressions and gestures while singing during her performance at New York’s Versailles nightclub, 1952.

Allan Grant The LIFE Picture Collection/Getty Images

Shelley Winters in a booth with mirrors, 1949.

Shelley Winters in a booth with mirrors, 1949.

Allan Grant The LIFE Picture Collection/Getty Images

Marcel Duchamp with Dada artwork, 1953.

Marcel Duchamp with Dada artwork, 1953.

Allan Grant The LIFE Picture Collection/Getty Images

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