As you may have heard, Irving Penn, the famous photographer who shot virtually every celebrity and famous designer from the late 1940s onward, died yesterday at the age of 92 at his Manhattan home. Aside from his fashion photography for Vogue, Penn was probably best known for capturing playful and intense moments with some of the greatest artists and icons of the 20th century, as you’ll see in our listicle of 25 Amazing Irving Penn Portraits.

Pablo Picasso

Yves Saint Laurent

Woody Allen

Simone de Beauvoir

Salvador Dali

Cecil Beaton

Truman Capote

Richard Avedon

Igor Stravinsky

Colette

Francis Bacon

Eugene Ionesco

Nadja Auermann

Claude Lévi-Strauss

Barnett Newman

Marlene Dietrich

Marcel Duchamp

Jacob and Gwen Lawrence

Tennessee Williams

Sophia Loren

Alberto Giacometti

S.J. Perelman

Kate Moss

Jean Cocteau

Ingmar Bergman