The Stories Behind Some of the 20th Century’s Most Iconic Portraits

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The portrait, as far as we’re concerned, is one of the most arresting forms of art. Not only does it portray a person, but it can affix a million meanings or emotions to that person, adding to and possibly conflicting whatever baseline emotions their visage stirs up in the viewer. Here, we’ve collected a few of what can best be described as the most iconic portraits of the most iconic figures, from musicians to actors to artists to politicians. Note: we’re not claiming that these are the most iconic figures of the 20th century hands down (although some would definitely make the cut), but rather that these portraits rank among the most powerful and enduring photographic images of the century. Indeed, many of these photographs have transcended their subjects to become iconic in their own rights as images — for instance, even those who have no idea who Che Guevara is would probably recognize his face as captured by Alberto Korda and spray-painted on a t-shirt. Click through to see 10 of the most enduring portraits of pop culture icons taken in the 20th century, and since of course there are many more that could have been included on this list, be sure to chime in with your own suggestions in the comments.

“Guerrillero Heroico” (“Heroic Guerrilla Fighter”) by Alberto Korda, 1960

This iconic photograph of Che Guevara was taken in Havana on March 5, 1960 at a memorial service for victims of the La Coubre explosion. Korda, a supporter of the Cuban Revolution, said he snapped the photo at a time when Guevara’s face showed “absolute implacability.” Though a slightly modified version of this portrait has been used over and over again on products and in media, Korda has never asked for any royalties, wanting the image to spread as much as possible to reinforce Guevara’s ideals. However, he did protest whenever the image was applied to products he thought Guevara would not approve of, such as alcohol, successfully suing Smirnoff for using the photo in a commercial. He said, “As a supporter of the ideals for which Che Guevara died, I am not averse to its reproduction by those who wish to propagate his memory and the cause of social justice throughout the world, but I am categorically against the exploitation of Che’s image for the promotion of products such as alcohol, or for any purpose that denigrates the reputation of Che.”

“Jim Morrison, the Young Lion,” by Joel Brodksy, 1967

This photograph of Jim Morrison is by far the most famous of the many taken in the Doors’ 1967 “Young Lion” photo shoot. Less known than the photograph, perhaps, is that Morrison was stumbling drunk when it was taken. As Joel Brodsky himself illuminated, “I always thought it was sort of funny that the pictures of Morrison from that session were the most used. Jim was totally plastered… By [the end], he was so drunk he was stumbling into the lights and we had to stop the session. He wasn’t a wild drunk — actually he was kind of quiet — but his equilibrium wasn’t too terrific. Still, he was great to photograph because he had a very interesting look… You know, Morrison never really looked that way again, and those pictures have become a big part of The Doors’ legend. I think I got him at his peak.” Well, drunk or not, those are the eyes of a legend.

Albert Einstein by Arthur Sasse, 1951

This photo was taken on Einstein’s 72nd birthday (March 14, 1951), on his way back from an event in his honor. Supposedly, his car surrounded by the press, he shouted “That’s enough, that’s enough!” (the man had been posing and smiling for the cameras quite a lot that day), but no one paid much heed. Luckily for Sasse, who was begging for a smile, Einstein stuck out his tongue instead, and the photographer snapped what is now the most famous photo ever taken of the physicist. Indeed, even Einstein liked the photograph so much that he cropped out the scene and his companions in the car and made copies of it to send as a greeting card to his friends. And who can blame him?

Yoko Ono and John Lennon by Annie Leibovitz, 1980

This iconic photograph was shot for the cover of Rolling Stone on December 8, 1980. Though the magazine had asked for a photo of Lennon alone, he had insisted that Ono be included, and so Leibovitz relented and planned to recreate the cover of Double Fantasy. Of the ensuing iconic image, Leibovitz explained, “What is interesting is she said she’d take her top off and I said, ‘Leave everything on’ — not really preconceiving the picture at all. Then he curled up next to her and it was very, very strong. You couldn’t help but feel that she was cold and he looked like he was clinging on to her. I think it was amazing to look at the first Polaroid and they were both very excited. John said, ‘You’ve captured our relationship exactly. Promise me it’ll be on the cover.’ I looked him in the eye and we shook on it.” Lennon was fatally shot a mere five hours later — Leibovitz would be one of the last people to photograph him, and the very last to do so professionally.

“Picasso and the Loaves,” by Robert Doisneau, 1952

French photographer Robert Doisneau is probably best known for his much posterized photograph “Le Baiser de l’Hotel de Ville,” taken in 1950. However, interested in street culture and the playfulness inherent in everyday life, he also shot this iconic portrait of Pablo Picasso. As Doisneau described the event: “When I arrived at Villauris, Picasso was having lunch with his wife and we talked, but we didn’t shoot any pictures. I came back the next day having realized by then that Picasso had a great sense of the ridiculous. I went to a baker I knew, who made the bread rolls that are on the table. The baker used to call them Picasso’s hands. When people pointed out that they had only four fingers he’d say, ‘Of course, that’s why they’re called Picasso’s hands.’ So I bought the rolls and put them in front of Picasso and took the photograph. You know he loved to make jokes – we spent two days joking all the time. Picasso was the best model I ever had. Everyone coming close to him received some gold dust.”

“The Roaring Lion,” by Yousuf Karsh, 1941

Karsh took this photograph of Churchill on December 20, 1941, just after Churchill’s speech to the Canadian House of Commons in Ottawa. Oft reported to be the most reproduced photographic portrait in history, it was snapped just as Karsh took away Churchill’s cigar. As described by the photographer in Faces of Our Time, “He was in no mood for portraiture and two minutes were all that he would allow me as he passed from the House of Commons chamber to an anteroom. Two niggardly minutes in which I must try to put on film a man who had already written or inspired a library of books, baffled all his biographers, filled the world with his fame, and me, on this occasion, with dread.” After Churchill walked into the room scowling, “Instinctively, I removed the cigar. At this the Churchillian scowl deepened, the head was thrust forward belligerently, and the hand placed on the hip in an attitude of anger.” Later, Churchill told Karsh, “You can even make a roaring lion stand still to be photographed,” hence the title of the photograph, which ultimately made the cover of Life magazine.

Demi Moore by Annie Leibovitz, 1991

This photograph, which originally appeared on the cover of Vanity Fair in 1991, caused an enormous scandal and is still referenced today in many types of media. Leibovitz, who already had a relationship with Moore and her then-husband, Bruce Willis, having photographed them many times, was commissioned to shoot a cover of the pregnant Moore. She dressed her in glamorous attire and took many photographs, capturing this one only at the end and intending for it to be just for Moore and Willis. However, when she looked at the proofs, she realized the photo would be a perfect cover shot, and Moore agreed readily. Leibovitz told Vanity Fair a few years ago, “It was a popular picture and it broke ground, but I don’t think it’s a good photograph per se. It’s a magazine cover. If it were a great portrait, she wouldn’t be covering her breasts. She wouldn’t necessarily be looking at the camera. There are different criteria for magazine covers. They’re simple. The addition of type doesn’t destroy them. Sometimes they even need type. My best photographs are inside the magazine.” Regardless, this is the one that has risen to iconic, copied, obsessed-about status.

Jimi Hendrix by Jim Marshall, 1967

At the 1967 Monterey International Pop Festival, Jimi Hendrix finished his set with an insane version of “Wild Thing,” then poured lighter fluid onto his Fender Stratocaster and set it aflame before smashing it seven times and throwing the pieces to the audience. Until this moment, The Jimi Hendrix Experience had been more or less ignored by American audiences, but Hendrix’s wild performance sparked interest (ahem, sorry) in the band and their career immediately took off. This photograph by Jim Marshall, himself a legend in the rock world as one of the photographers closest to the musicians (for instance, he was the only photographer allowed backstage for the Beatles’s final concert), became an iconic image, covering the 20th anniversary issue of Rolling Stone and drawing reference everywhere.

Marilyn Monroe by Matthew Zimmerman, 1954

Though there are many photographs of Marilyn Monroe that have reached iconic status — and the number is, if anything, growing — this snapshot is at the top of the list. In this September 9, 1954 publicity shot for The Seven-Year Itch, Marilyn Monroe stands over a New York City subway grate, her skirt flying up way further than it actually did in the film (that scene was reshot on a soundstage because the actual street was much too loud).

Bob Dylan by Barry Feinstein, 1966

Like Monroe, there are a million iconic photographs of Bob Dylan, but few are as well known as those taken by Barry Feinstein while he followed Dylan and the Band on their 1966 tour of Britan. In this shot, taken in London from the inside of the singer’s limousine, fans look in as if praying while Dylan blithely ignores them. Feinstein’s photography exposed Dylan as an even more controversial figure than he had been before, showing both fragility and pomp. As The Guardian observes, “Often he looks gaunt and fragile, his eyes hidden behind ever-present shades, his body hunched against the cold British winds and the imploring eyes of his faithful.” Feinstein died this year — see even more iconic photos of Bob Dylan by the photography great here.