Allan Grant Photographs from LIFE

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.