From the glitzy post-war fashion layouts for Vogue Magazine to the celebrity portraits that helped define his work.
Everyone from a soulful Pablo Picasso to a shy smiling Audrey Hepburn to an exotic and distant Marlene Dietrich. Jeff Rosenheim is a curator with the Metropolitan Museum of Art, which loaned the Penn collection.
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"He traveled the world with his camera. But in New York, he was able to explore people who were coming through the city, he was in the right place at the right time, he was a master technician. The pictures are amazing. He was a great image maker, but he was a splendid object maker," said Rosenheim.
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But in the 1960s Penn turned his lens on San Francisco and the Summer of Love. Capturing formal group portraits of bands like the Grateful Dead, with Big Brother and the holding company. And giving middle America its first look at San Francisco's hippies complete with young families.
de Young curator Emma Acker says Penn was even able to coax members of the Hell's Angels motorcycle club into his formal backdrop by giving them easy access to a studio in Sausalito.
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"He actually told them to ride on up the freight elevator of the building on their bikes and immediately begin posing. And he described them as coiled springs ready to fly loose and make trouble he said he breathed a huge sigh of relief when they're screaming bikes went down the road. But he's really sort of contained them in this space. And there's this wonderful sense of energy and defiance and some vulnerability that I think comes across," said Acker.
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In the end, it is a century of American life. Captured with the technical precision and relaxed formality of a portrait photographer whose work captured its energy, across the decades.
The Irving Penn Retrospective opens this weekend and runs through the middle of July.