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

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.”