Phil Stern (1919 – 2014): Classic Hollywood Portraits

Update (Dec. 14, 2014): Phil Stern, the celebrated photographer known for his classic Hollywood portraits, died on Dec. 13. He was 95. “I am honored and privileged to have worked with Phil over the last 20 years,” says Geoff Katz, Stern’s agent at CPi. “It has been an amazing journey, he was ‘one of a kind’.”

The 60-year career enjoyed by Phil Stern, who recently turned 95, is one of the most varied and downright extraordinary of any 20th century photographer. Awards and honors have, rightly, been heaped on Stern through the years, and this weekend, in celebration of his 95th birthday, the Philadelphia native will donate 95 of his classic Hollywood portraits and World War II pictures to the Veterans Home of California in West Los Angeles.

A decorated WWII Army vet himself—he was one of the storied “Darby’s Rangers” (1st Ranger Battalion) who saw so much action in North Africa and Sicily in 1943—Stern returned from war, shot for major magazines like LIFE and Look, worked on motion pictures like Judgment at Nuremberg and Guys and Dolls and photographed jazz album covers for labels like Verve and Reprise.

The names of the actors, actresses and musicians he photographed, meanwhile, reads like a Who’s Who of 20th-century legends, including James Dean, Orson Welles, Marilyn Monroe, Marlene Dietrich, Marlon Brando, Joan Crawford, Lauren Bacall, Humphrey Bogart, John Wayne, Count Basie, Dizzy Gillespie, Judy Garland, Billie Holiday, Frank Sinatra, Elizabeth Taylor, Audrey Hepburn and on and on.

He recently told LIFE.com, through a mutual friend, that the one person he wishes he’d photographed, but never did, was Charlie Chaplin. Asked what a photographer needs in order to do consistently solid work, he replied: “Access and a level of comfort with your subjects. They need to feel at ease. I think [celebrities] felt comfortable with me. They allowed me to photograph them undisturbed. It was just pure luck.”

Of the famous “sweater pictures” he made with James Dean—the two met and became fast friends after Stern’s car narrowly missed Dean’s motorcycle when the actor ran a red light—he modestly avers that he “really had nothing to do with that. It was all Dean’s doing.”

Here, in tribute to the man and his decades of phenomenal work, LIFE.com presents a small selection of Phil Stern’s unforgettable pictures of creative titans and pop-culture icons.

[See more at Phil Stern’s Archives]