At first, the Hollywood studios ran a closed shop, so freelance photographers working for magazines were barely allowed on set, relegated instead to photographing actors in their dressing rooms or before and after filming. Bob Willoughby turned that limitation into an asset, creating photographs that were unstudied, intimate, and revealing—works of art, really, that would one day find themselves in the permanent collections of the National Portrait Gallery in Washington, D.C.; the Museum of Modern Art and the Metropolitan Museum of Art, in New York; and London’s National Portrait Gallery and Tate Gallery Collection.

Considered Hollywood’s first behind-the-scenes photographer, Willoughby chronicled the making of some of America’s greatest films, including My Fair Lady, A Star Is Born, Rebel Without a Cause, The Caine Mutiny, Who’s Afraid of Virginia Woolf?, and The Graduate. Director Sydney Pollack felt that Willoughby had captured the soul of his film They Shoot Horses, Don’t They? in a single photograph of a deeply despairing Jane Fonda. Now the best of his stunning portraits of Hollywood stars and jazz artists, many of which first appeared in Life and Look, have been collected by Willoughby’s son Christopher in a new book.

Among the treasures in Bob Willoughby: A Cinematic Life are Kim Novak and Frank Sinatra suffering magnificently for The Man with the Golden Arm; a haunted Julie Christie in a raincoat on the set of Petulia; James Dean, his collar askew, intently studying his script for Rebel Without a Cause; Anne Bancroft and Dustin Hoffman being directed by Mike Nichols during the filming of The Graduate; Jean Seberg making Bonjour Tristesse (capturing her “wide-open blue eyes” with “a glint of boyish malice,” in François Truffaut’s words); and an impossibly beautiful Elizabeth Taylor in antebellum costume for Raintree County and, just nine years later, braying at Richard Burton in Who’s Afraid of Virginia Woolf?

Director Sydney Pollack felt that Willoughby had captured the soul of his film They Shoot Horses, Don’t They? in a single photograph of a deeply despairing Jane Fonda.

Audrey Hepburn was a favorite subject, and he worked with the elfin actress “on half a dozen films,” says Christopher. “Taschen published a wonderful book of my father’s images of Audrey … [They] hit it off the first day they met.” As for Marilyn Monroe, Christopher recalls in an interview with Classiq Journal, “the first time he photographed Marilyn was at a Photo Op at Fox Studio, not really dad’s sort of thing.… As Marilyn came towards him, he looked down into the camera and felt the hair on the back of his neck rising. He said he realized then what all the shouting was about.”

Willoughby’s photographs of jazz greats—Louis Armstrong, Duke Ellington, Miles Davis, Billie Holiday, Dave Brubeck, Ornette Coleman—remind us of the richness of America’s innovative, unforgettable music. Chet Baker is a tender, doe-eyed youth photographed alone and lonely after recording “My Funny Valentine”; a smiling Satchmo cradles his trumpet on the set of High Society; Frank Sinatra, at a recording-studio session for The Man with the Golden Arm, is dapper as always.

How did he manage to get such intimate and vulnerable shots? “Dad treated the actors, directors, and crews—whomever he was shooting—as fellow professionals,” Christopher wrote. “He also had a pretty solid sense of his own worth. He told Barbra Streisand once, when she was being a little difficult, that he was at least as good a photographer as she was a singer, and could we just get to work?”

Sam Kashner is a Writer at Large for AIR MAIL.Previously a contributing editor for Vanity Fair, he is the author or co-author of several books, including Sinatraland: A Novel, When I Was Cool: My Life at the Jack Kerouac School, and Life Isn’t Everything: Mike Nichols, as Remembered by 150 of His Closest Friends

Nancy Schoenberger is the author of several books, including Wayne and Ford: The Films, the Friendship, and the Forging of an American Hero. Her next book, Blanche: The Life and Times of Tennessee Williams’s Greatest Creation, will be published by HarperCollins in April