Legendary painter Hans Holbein was in a difficult situation. In 1539, he was sent by Henry VIII of England to paint the unmarried Anne of Cleves, whose family was an important strategic ally of Britain. The temperamental Henry, with three wives already under his large belt, had been assured of Anne’s beauty. “Every man praiseth the beauty of the same lady as well for the face as for the whole body,” he was told by adviser Thomas Cromwell, “she excelleth as far the duchess [of Milan] as the golden sun excelleth the silver moon.”

Holbein’s painting was to serve as confirmation of these verbal reports. With Cleve’s court officials looking over his shoulder, Holbein was expected to paint Anne in a way that was both flattering and realistic. The resulting painting presented a pleasant, docile looking woman—and it seems Henry was cheered by what he saw. Two copies were made: one is now at the Louvre in Paris, and the other at the Victoria and Albert Museum in London. Although scholars debate how important Holbein’s work was in Henry’s decision making process, it is doubtful he would have agreed to marry her without having viewed the flattering portrait.

Unfortunately, upon their meeting on New Year’s Day, 1540, Henry was immediately repulsed by Anne’s actual appearance, shouting to advisors, “I like her not.” Their marriage lasted only six months, and their subsequent divorce would lead to two more marriages for Henry—and one more beheading—before his death in 1547. Fortunately, Anne would survive both Henry and all his other wives, and live a relatively happy and tyrant-free life in England.

On June 28, 1914, Archduke Franz Ferdinand, the heir presumptive of the Austro-Hungarian empire, and his wife, Sophie, were fatally shot by Serbian nationalist Gavrilo Princip while riding in a motorcade in Sarajevo. As they were both dying, Franz Ferdinand said to his wife, “Don’t die darling, live for our children.”

It was the shot heard—and seen—around the world. The assassination that would spark WWI was covered by photo journalists in real time. In Europe and America, photos of the players in the tragedy were disseminated in newspapers and magazines like the _Illustrated London New_s, giving people a personal, immediate view of the tragedy.

Photographers had captured the couple as they entered the car that they would die in minutes later, the violent capture of Princip, and the Archduke and his wife lying in state in open caskets, side by side. Supplemented with graphic illustrations of the actual assassination and photos of the orphaned children of the royal couple, these images personalized the assassination, no doubt helping to prime the allies for war.

Perhaps no royal image has caused more controversy throughout history than Spanish master Francisco Goya’s 1800 portrait of the royal family of Charles IV. Although Goya’s (who was the official painter at the Spanish court) motives are unclear, there is no doubt he portrayed the family in a harsh, realistic and unflattering light, unheard of in official royal representation before this time.

Called by French writer and critic Theophile Gautier a “portrait of the owner of the corner grocery and his wife,” the painting of the extended Bourbon family has long been seen as political commentary of the weak, corrupt Spanish monarchy. One critic wrote that Goya, who makes a cameo in the painting, appears to place the family on a “stage facing the public, while in the shadow of the wings the painter, with a grim smile, points and says: ‘Look at them and judge for yourself!”

However, others believe the painting is revolutionary in a different way: by showing a fallible royal family, it allows viewers to see them not as the gods and goddesses of the past, but as real people. “A quick survey of the faces along a supermarket’s aisles,” a reader wrote to Harper’s Magazine in 1842, “confirms that the Spanish royal family, as portrayed by Goya in 1800, was no more and no less ugly than the rest of us are now.” In other words: royals, they’re just like us!

It was a poignant image. Princess Diana, sitting demurely, all alone in front of the Taj Mahal, the ultimate symbol of royal romantic love. Eleven years earlier, her husband, Prince Charles, had promised to bring her to the iconic site. Now that they were finally in India, he had decided to not go with her. The war of the Windsors had reached a fever pitch.

Diana made the savvy decision to keep her advisors and companions out of the pictures taken that day. Pictures of the visit were soon on the front page of every tabloid, a pointed visual symbol of the emotional end of her marriage. “Her famous pose outside the Taj Mahal in February 1992, a forlorn and lonely princess at the world’s largest monument to love,” the New York Post noted, “laid the groundwork for her story arc—no matter that Charles was actually on the trip.” On December 9, 1992, the couple’s official separation was announced.

1787 was a rough year for Queen Marie Antoinette. Her reputation had been shredded by the infamous “Affair of the Necklace,” France was facing massive deficits and poverty, and her husband, King Louis XVI, was escaping his problems by drinking and hunting. Desperate to change her image from that of a flighty, uncaring Austrian into the stoic, majestic and nurturing “mother of the children of France,” she commissioned her favorite painter, Elisabeth Louise Vigée Le Brun, to paint a portrait (now at Versailles) of her with her sons and daughters for the public to view.

Le Brun based her composition on Renaissance portraits of the Holy Family. According to Antonia Fraser’s book, Marie Antoinette: The Journey, every detail of the painting was carefully considered. Even though the Queen favored simpler English dresses, in the portrait she wore rich, imposing French court dress. Adding to Marie Antoinette’s strife, her younger daughter Sophie died before the portrait was finished, which caused Le Brun to paint the child out of the composition.

The painting would not be viewed by the public. Hatred of the queen became so intense that Paris Police Chief Lenoir requested that she not show the painting because it would become a lightning rod for demonstrations and riots. The painting was withdrawn, and in its empty frame at the Salon of the Royal Academy a joker pinned a note which read, “Behold the Deficit!”

One of the most famous artworks in history, this bust of Egyptian Queen Nefertiti (now at Berlin’s Neues Museum) signifies much more than an uncommonly beautiful face. The sensuality and suppleness of Nefertiti’s symmetrical face, her full, smiling lips and arching neck portray a woman of flesh and blood—a far cry from the cold, rigid portraits of previous Pharaohs. It represents a religious revolution spearheaded by Nefertiti and her husband, Amenhotep IV (later changed to Akhenaten), who reigned from 1353-1336 BCE, during what is known as the Amarna period.

For millennia, Egyptian Pharaohs—and thus the Egyptian people—had worshiped multiple gods. All this changed in 1353, when Akhenaten came to power. He worshiped a single god, “Aten,” a sun-god. With the old religion effectively banned, the royal family carried out a propaganda effort through royal art and architecture, personalizing and individualizing the historically impersonal royal image. The new religion’s focus on the present instead of eternity “is perhaps most recognizable in the immediate, dynamic quality of Amarna relief and painting,” scholar James P. Allen writes in The Royal Women of Amarna, “as compared with the more formal, static quality that usually characterizes Egyptian art.”

This religious and artistic revolution would be short lived. After Akhenaten’s reign, his religion was discarded, and many of the artworks created in the sun-god Aten’s name were repurposed or destroyed. But Nefertiti’s haunting face lives on.

The opportunist artist Jacques Louis David, who served whoever was in power, painted this massive propaganda piece to celebrate the 1804 crowning of Napoleon and Josephine in Notre Dame Cathedral. The painting helped visually cement Napoleon’s power as absolute emperor, using classical allusions and “historic revision” (Napoleon’s disapproving mother was not at the ceremony, but she is in the painting) to inform France and the world that Napoleon was creating a new Roman Empire.

The painting, which was modeled after Reuben’s Coronation of Marie de Medici, served as a kind of who’s who of the Napoleonic Empire. Napoleon’s family and key ministers and officials (including David himself) are all portrayed in the revisionist “classical” Roman clothing of the new empire, and depicted reverently observing the ceremony inspired by the Pope’s crowning of the Holy Roman Emperor Charlemagne in the 9th century.

The finished painting was displayed in the Louvre, where it still resides. It made such an impact that there’s even a painting of the public viewing it: Louis Léopold Boilly’s The Public Viewing David’s “Coronation” at the Louvre, from 1810, shows a massive group of people looking at the painting, while a soldier reads out the important leaders it depicts, lest the public forget who was in charge.