Written By: Ben Cosgrove

The great Alfred Eisenstaedt’s photographic vision wasn’t limited to the intimate portraits he produced of some of the 20th century’s most famous faces, from Marilyn Monroe and Frank Lloyd Wright to Mia Farrow and J. Robert Oppenheimer. After researching seemingly endless negatives, contact sheets, and Eisenstaedt prints, LIFE.com’s Liz Ronk rediscovered that the long-time LIFE photographer very often crowned his assignments with one last shot: creating captivating self-portraits, posing and frequently clowning with his subjects.

The realization that “Eisie” (as he was known by those lucky enough to call him a colleague or a friend) often turned the lens on himself in this way is likely to astonish photography aficionados and casual fans alike. Throughout his six-decade career, Eisenstaedt made some of the most immediately recognizable and most frequently reproduced images of the 20th century; that he also clearly enjoyed “playing tourist” and posing with the rich, the famous and the powerful as well as men and women whose names and occupations have been lost to history somehow brings the masterful photojournalist that much closer.

This legendary man, these self-portraits suggest, is actually more like many of us than we might have thought.

Eisenstaedt also famously carried with him an autograph book that, by the end of his life, was filled with page after page of signatures from long-forgotten artists, fellow photographers, legendary athletes, powerful world leaders in short, from anyone and everyone he happened to shoot.

The man’s habit of photographing himself with his subjects, and even asking for their autographs for his ever-growing collection, was not only well-known among by his colleagues at LIFE and elsewhere, but in at least one instance the seemingly whimsical tradition appears to have had a lasting influence on one of his younger peers. The celebrated sports photographer Neil Leifer recently told LIFE.com that early in his career, the notion of asking someone to pose for a picture after a shoot, or requesting an autograph of someone he had just finished shooting, struck him as vaguely unprofessional. It just was not something that a credible photojournalist did. Or so he thought.

“In the early 1980s I had an office next to Eisie’s in the Time-Life Building,” Leifer recalls, “and I saw that in his office he had framed photos of himself with JFK, Sophia Loren all these pictures where he was posing with people he had photographed on assignments for LIFE, and I thought, If Alfred Eisenstaedt, of all people, takes self-portraits with his subjects, and asks them for autographs, how unprofessional can it really be?

Here, then, in tribute to the endearing penchant of one of the 20th century’s indispensable photographers a penchant to add a quiet, personal, visual coda to so much of his life’s work LIFE.com offers a selection of some of the most revealing and unexpected of Alfred Eisensteadt’s singularly charming self-portraits.

Liz Ronk edited this gallery for LIFE.com. Follow her on Twitter @lizabethronk.

Marilyn Monroe and Alfred Eisenstaedt at Monroe's Beverly Hills home, 1953.

Marilyn Monroe and Alfred Eisenstaedt at Monroe’s Beverly Hills home, 1953.

Alfred Eisenstaedt Time & LIfe Pictures/Shutterstock

Alfred Eisenstaedt and Wataru Narahashi, Japanese cabinet minister, Tokyo, March 1946.

Alfred Eisenstaedt Time & Life Pictures/Shutterstock

Alfred Eisenstaedt and LIFE's National Affairs Editor, Hugh Moffett, on assignment in Kenya, 1966.

Alfred Eisenstaedt and LIFE’s National Affairs Editor, Hugh Moffett, on assignment in Kenya, 1966.

Alfred Eisenstaedt Time & Life Pictures/Shutterstock

Alfred Eisenstaedt and Walt Disney, California, 1946.

Alfred Eisenstaedt and Walt Disney, California, 1946.

Alfred Eisenstaedt Time & Life Pictures/Shutterstock

Alfred Eisenstaedt with Jackie Kennedy and Caroline Kennedy in Hyannis Port, Massachusets.

Alfred Eisenstaedt with Jackie Kennedy and Caroline Kennedy in Hyannis Port, Massachusetts, 1960.

Alfred Eisenstaedt Time & Life Pictures/Shutterstock

Alfred Eisenstaedt and former sumo wrestling champion Tomojiro Sakata, Tokyo, 1946.

Alfred Eisenstaedt Time & Life Pictures/Shutterstock

President John F. Kennedy and Alfred Eisenstaedt in the Oval Office, 1962

President John F. Kennedy signs Alfred Eisenstaedt’s autograph book after a portrait session in the oval office, 1962.

Alfred Eisenstaedt Time & Life Pictures/Shutterstock

Alfred Eisenstaedt poses with “beauty culturist” and the first woman to star in her own daily exercise TV show, Debbie Drake, 1962.

Alfred Eisenstaedt Time & Life Pictures/Shutterstock

Alfred Eisenstaedt with artist Afewerk Tekle in Ethiopia, 1955

Alfred Eisenstaedt with student-artist Afewerk Tekle, 22, in Ethiopia, 1955. Tekle went on to become one of Ethiopia’s most celebrated painters.

Alfred Eisenstaedt Time & Life Pictures/Shutterstock

Alfred Eisenstaedt and Emperor of Ethiopia Haile Selassie, Addis Ababa, 1955.

Alfred Eisenstaedt and Haile Selassie

Alfred Eisenstaedt Time & Life Pictures/Shutterstock

Sophia Loren and Alfred Eisenstaedt in the bedroom of her Italian villa, 1969.

Sophia Loren and Alfred Eisenstaedt in the bedroom of her Italian villa, 1969.

Alfred Eisenstaedt Time & Life Pictures/Shutterstock

Alfred Eisenstaedt and Alice Austen in Staten Island, NY

Alfred Eisenstaedt pushes photographer Alice Austen in a wheelchair, Staten Island, New York, in 1951, one year before Austen died.

Alfred Eisenstaedt Time & Life Pictures/Shutterstock

Alfred Eisenstaedt on assignment in India, 1963

Alfred Eisenstaedt poses with two unidentified local men while on assignment for LIFE in India in 1963.

Alfred Eisenstaedt Time & Life Pictures/Shutterstock

In a photograph taken by LIFE colleague Bill Shrout, Alfred Eisenstaedt kisses an unidentified woman reporter in Times Square on VJ Day, August 14, 1945 a powerful visual echo (in retrospect) of the now-iconic, era-defining “sailor kissing a nurse” picture that Eisenstaedt himself shot that very same day.

William C. Shrout Time & Life Pictures/Shutterstock

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