8 Famous Portraits and the Secrets of the People in Them

For centuries, art historians debated who Leonardo da Vinci actually painted in his most famous work. Was she a noblewoman? A merchant’s wife? Leonardo himself? The answer arrived in 2005, when German scholars discovered a handwritten note in the margins of a book at the University of Heidelberg. The note, scrawled by a Florentine city official named Agostino Vespucci in October 1503, specifically named Lisa del Giocondo—wife of a silk merchant named Francesco del Giocondo—as the subject Leonardo was painting. After 500 years of guessing, the mystery had been hiding in a library all along.

That said, the painting still keeps a few puzzles. Her missing eyebrows (fashionable women of the time plucked them) and the unusual haziness of the background, created with Leonardo’s technique of sfumato, have kept scholars busy for generations. Whatever else she was, Lisa del Giocondo was a real woman—a Florentine wife whose husband commissioned a portrait, and who ended up staring down half the human race.

Johannes Vermeer’s 1665 painting has the pull of a portrait—those wide eyes, that glance over the shoulder, that single luminous earring—but it was never meant to be one. Art historians classify it as a tronie, a Dutch term for a type of idealized figure study showing a generalized character type rather than a specific sitter. Vermeer wasn’t depicting a real person so much as exploring light, texture, and the idea of a face. The exotic blue-and-gold turban further signals something imagined rather than observed.

That hasn’t stopped people from speculating. Writers and filmmakers have proposed the girl was Vermeer’s own daughter, or a household servant, or a muse. Tracy Chevalier turned the mystery into a best-selling novel in 1999, which became a film starring Scarlett Johansson. The irony is that the painting’s power lies precisely in having no particular person behind it—she belongs to everyone who looks at her.

Jan van Eyck’s 1434 painting of a well-dressed Flemish couple is celebrated as much for what’s behind them as for what’s in front of you. On the far wall hangs a tiny convex mirror, and if you look closely at the reflection inside it, you can make out two additional figures standing in the doorway. Art historians have long suggested that one of them may be van Eyck himself—which would make this one of the earliest self-portraits in Western art, hiding in plain sight inside another painting.

Above the mirror, van Eyck inscribed in ornate Latin script: Johannes de Eyck fuit hic—“Jan van Eyck was here.” The inscription has the swagger of a tag left at a scene. For decades, the painting was described as a wedding document, but that theory has largely fallen out of favor with art historians at the National Gallery in London, who now see it simply as a double portrait of two prosperous Bruges merchants.

Grant Wood spotted a small white farmhouse in Eldon, Iowa in 1930 and immediately imagined the kind of people who might live in a place with that severe Gothic window. He asked his dentist, Dr. Byron McKeeby, and his own younger sister, Nan Wood Graham, to pose for the two figures. Nan was furious when the painting became famous—people kept mistaking her for the old farmer’s wife. She spent the rest of her long life insisting, firmly, that the figures were a father and his daughter, not a married couple.

The painting debuted at the Art Institute of Chicago’s annual exhibition and won a bronze medal and $300. Many Iowans were deeply offended, believing Wood was mocking rural life. He wasn’t—he admired the stoicism he saw in Midwestern faces—but the misreading stuck. The painting went on to become one of the most parodied images in American art, and Nan Wood Graham posed in front of it again in 1942, still not quite smiling.

You almost certainly know this painting as Whistler’s Mother, but James McNeill Whistler gave it a much cooler, more calculated title: Arrangement in Grey and Black No. 1. He wanted viewers to focus on the composition as a study in tone and form, not on the sentimental fact that his mother was sitting there. Victorian audiences found the aesthetic approach baffling, and when the painting was submitted to London’s Royal Academy in 1872, the title had to be extended to include “Portrait of the Painter’s Mother” before the committee would hang it.

As for why Anna Whistler was sitting there in the first place—the original model for that session simply didn’t show up. His mother, visiting him in London, offered to fill in. She stood for a while, but it proved too tiring, so Whistler had her sit. What began as a last-minute substitute became one of the most recognized images of motherhood in Western art. The French government purchased it in 1891, and it now hangs permanently at the Musée d’Orsay in Paris—the first American painting to enter the Louvre’s collection.

Diego Velázquez painted Las Meninas in 1656 as a royal commission—and then did something quietly audacious. He put himself in the painting, standing at a large canvas on the left side of the composition, brush in hand, apparently in the act of creating the very image you’re looking at. For a court painter to place himself so prominently in a royal work was a remarkable assertion of status. Velázquez had spent decades trying to prove that painting was a noble art, not a craft.

On the back wall, a mirror reflects the blurry images of King Philip IV and Queen Mariana—the subjects Velázquez may be painting on that unseen canvas. Scholars still debate exactly what the mirror shows: is it reflecting the royal couple standing where you, the viewer, are standing? Or does it show the painting-within-the-painting? The ambiguity is almost certainly intentional. Las Meninas has been called the world’s greatest painting by more than one critic, and its refusal to be easily read is a large part of the reason why.

Edvard Munch’s 1893 image of an anguished figure against a blood-red sky is not really a portrait of an external threat—it’s a record of an internal one. Munch described the experience that inspired it in his diary, dating the entry to January 22, 1892. He was walking at sunset with two friends when, as he wrote, the sky turned “an infinite scream passing through nature.” He stood trembling with anxiety while his companions walked on, apparently unaffected.

Some researchers have proposed the dramatic sky was caused by the long-lasting atmospheric effects of the 1883 Krakatoa eruption, which sent vivid sunsets around the world for months. Others suggest he may have seen an aurora borealis. But Munch himself was clear that what terrified him came from inside his own mind, not the sky. He was a man who had experienced enormous personal loss, and he lived near a psychiatric hospital where his sister was committed. The screaming figure isn’t screaming—it’s covering its ears against a scream it hears everywhere.

When John Singer Sargent exhibited this painting at the 1884 Paris Salon, the reaction was swift and brutal. Critics called it vulgar. The public was offended by the sitter’s powdery white skin, her lavender-tinged complexion, and the daring cut of her black gown. But the detail that caused the most trouble was a single dress strap painted slipping off her right shoulder—a small thing that read, in the Victorian moral atmosphere, as deeply improper. Sargent quietly repainted the strap to its upright position before the close of the exhibition.

The sitter was Virginie Amélie Avegno Gautreau, an American-born socialite married to a wealthy French banker. Many viewers recognized her despite the painting’s anonymous title. The scandal damaged both their reputations, and Sargent soon moved his career to London. He kept the painting for decades, eventually selling it to the Metropolitan Museum of Art in New York in 1916. Today it’s considered one of the great masterworks of American art. Sargent reportedly said it was “the best thing I have done.”