10 historical figures who are celebrated through their portraits and 10 who have been unfairly criticized

Holbein’s portraits depict a titan: broad-shouldered, with an imposing physical presence, exuding great authority through his confident stance. At the time these paintings were created, Henry was likely obese, suffered from leg ulcers, and had difficulty walking. The court painters knew what their craft required.

The Sun King was apparently about 1.63 meters tall and compensated for his short stature with imposing wigs, high-heeled shoes, and a court culture centered on ostentatious magnificence. His portraits, replete with ermine and heroic poses, do everything possible to make up for those few centimeters, and his teeth—notoriously in poor condition—curiously never appear.

Elisabeth’s later portraits were less works of art than propaganda: her face smoothed to the point of appearing timeless, her skin alabaster white, her gaze regal and inscrutable. At sixty, she had lost most of her teeth and concealed her smallpox scars under a thick layer of lead-based makeup, a fact that the portraits gave no hint of.

David’s large canvases depicting Napoleon crossing the Alps on a rearing horse are pure spectacle. The crossing actually took place on a mule, under far less spectacular conditions—a detail that David was not tasked with depicting.

The portrait by Gilbert Stuart that appears on the one-dollar bill was painted when Washington was in his sixties and wore ill-fitting dentures that distorted his jaw. It is said that Stuart deliberately left it unfinished so that he could continue to make copies of it to earn a living. The stiff, distant image we are familiar with owes as much to Stuart’s business model as it does to Washington’s actual face.

The idealized Cleopatra of European painting owes more to the imagination of the Renaissance than to historical sources. Coins minted during her reign depict a woman with striking features who had the bearing of a sovereign rather than a romantic ideal, and ancient sources suggest that her power stemmed from her intelligence and eloquence. Painters have, for the most part, ignored this.

The gentle, melancholic images that have come to define her likeness were painted long after her execution and reflect more the narrative of a martyr than the woman herself. Contemporary accounts describe her as a tall, imposing woman rather than a beauty in the conventional sense, and the portraits were created to fit the legend.

We have no portrait of Caesar that can be definitively identified as having been painted from life, but the image of a military genius with a slender face and striking features has endured through the centuries. Ancient busts suggest a face more marked by the passage of time, and it would appear that he was self-conscious about his thinning hair—a trait that sculptors treated with discreet kindness.

The image of the fearless warrior-king attributed to Richard I is largely a Victorian construct, designed to meet the needs of an era that required its medieval heroes to look the part. Contemporary sources describe a tall, imposing man, but the heroic visual tradition emerged several centuries later and served very specific interests.

The official portraits of Charlemagne were painted several centuries after his death. His biographer Einhard described him as a man with a potbelly, a high-pitched voice, and a neck that was too short for his build. The image of this majestic emperor in full ceremonial regalia is almost entirely an idealization.

Here are 10 historical figures whose portraits did not do them justice.

When Richard III’s skeleton was discovered beneath a parking lot in Leicester in 2012, it showed signs of scoliosis, but with a less pronounced curvature than tradition had suggested, and no atrophied arm. Shakespeare’s villainous hunchback had served as a visual model for centuries, and this was largely Tudor propaganda, driven by people who had good reasons to justify the dynasty that had replaced him.

Henry VIII rejected Anne of Cleves after meeting her, even though he had been charmed by Holbein’s flattering portrait. Contemporary accounts indicate that she was quite presentable. The insult “the mare of Flanders” came from Henry himself, who was no longer really in a position to judge appearances at that point, but this slander has nonetheless followed her throughout history.

Portraits of Cromwell are particularly unflattering compared to those of almost all other powerful leaders of his time: they depict him as a man with coarse features, sagging jowls, and an uncompromising demeanor. Whether this reflects his Puritan aversion to vanity or a tradition of hostile portraiture, history has bequeathed to us a charmless Cromwell rather than the imposing figure that his contemporaries also described.

Portraits of Catherine, particularly those circulated by her enemies, depict her in a particularly harsh light: always dressed in widow’s black, her face impassive, her demeanor cold. Protestant pamphleteers portrayed her as a sort of witch. The reality of a woman who managed to preserve the French crown throughout decades of religious wars is far more interesting than any painting suggests.

The iconic image of those dead, staring eyes and that cruel mouth comes from woodcut portraits created specifically to terrify Western European audiences. The legend of Dracula owes more to these woodcuts than to any other type of portrait worthy of the name. He was certainly brutal, but this visual tradition was intended to horrify, not to document.

Later historians and Protestant propagandists turned “Bloody Mary” into a caricatured, sinister figure, and her portraits followed suit. Contemporary sources describe a woman of small stature, often ill, under immense political pressure, whose methods were not out of step with those of her father Henry, but who lacked his talent for charm—and the portraits never sought to compensate for that.

Ivan IV’s nickname in Russian, “Grozny,” translates more accurately as “formidable” than “terrible”—a translation choice that has influenced all subsequent portraits in English. The images have favored the “terrible” version: a haggard gaze, a monstrous appearance. He was certainly a violent ruler, but this visual tradition reflected a deliberate framing by foreigners as much as it did reality.

Holbein also painted Thomas Cromwell, but while he flattered Henry, the portrait of Cromwell is uncompromising: it depicts a henchman carrying out a difficult task, without trying to hide it. After his execution, his image became a symbol of all the corruption in Tudor politics. The man who had spent decades keeping the machinery of government running was reduced to a face serving as a warning.

The busts of Socrates, created after his death, exaggerated his features—which were considered unattractive—to the point of turning them into a caricature: an exaggerated upturned nose and bulging eyes. It seems that he himself exploited this aspect to illustrate a philosophical reflection on inner beauty as opposed to outer beauty, but the artists who followed him in turn amplified this tendency, thereby cementing an image that undoubtedly exaggerated what was merely an ordinary face.

Roman busts depicting Agrippina show a strong and determined face, but the written sources were composed almost exclusively by male historians who perceived her political ambition as a threat. A woman displaying the same determination attributed to great Roman men was described as dangerous rather than formidable, and this perception became the prevailing view.