The 10 Most Unflattering Portraits Ever Made and the Stories Behind Them

For as long as humans have made art they’ve made portraits. And for as long as humans have made portraits they’ve made unflattering portraits. Whether because of an artistic off-day, a stylistic mismatch, or simply a hideous subject (sorry Habsburgs), even the greatest artists have rendered their subjects in ways that have shocked, offended or—worst of all—made us fall about laughing. And that’s just the greatest artists.

Nowadays we don’t have this problem. With the invention of photography, we no longer need to stand before a portrait artist or sit in sessions for hours on end so they can try to capture something of our likeness. We still have the option. But for those wanting instant gratification there are either our phones, cameras, or those caricature artists you always see sitting around famous historical monuments. And, of course, when it comes to the dissemination of our image, for better or for worse we have the Selfie.

Every historical age has its fair share of hilariously unflattering portraits. From the hapless Habsburgs (sorry again Habsburgs) and the demonic Danish Royal Family to former president George Bush’s woeful rendition of Vladimir Putin (so bad it’s a miracle it didn’t trigger World War Three), here are 10 of the most heinously unflattering portraits in history.

Ferdinand II of Spain by Michel Sittow

Plenty to get through and no better place to start than here, with this unflattering portrait of Ferdinand II. Not to be confused with the Holy Roman Emperor Ferdinand II (though he didn’t fare particularly well in his portraiture either; his trademark Habsburg Jaw meaning that he rather resembled a sausage), Ferdinand II was the King of Sicily, Aragon, Castile, Naples and Navarre.

Which might explain why he looks so very tired.

Ferdinand II of Spain by Michel Sittow (late fifteenth / early sixteenth century). Wikimedia Commons

There’s no evidence that he was a drinker—on the contrary, he was a devout Catholic. But from the tint of his eyes you’d be forgiven for thinking he’d been smashing the sauce the night before. Or that he’s channelling the Antichrist (which in the eyes of the Moors he may well have been). The early part of his reign was characterised by brutal fighting and forced conversions in Moor-held Spain. He was ruthlessly effective though, bringing to a close the several-century long period known as the Reconquista.

Ferdinand is most famous for patronising the Age of Discovery. It was he and his wife Isabella I who funded the expeditions of Christopher Columbus. We don’t know when this unflattering portrait was made, but considering he died in 1516 aged 63 we can reasonably guess it was sometime during this time in the late fifteenth century. He had a rather famous son-in-law, Henry VIII of England, with whom Ferdinand allied himself against the French and who, as we shall see in the next item, had his own fair share of unflattering portraits.

Michel Sittow’s other portraiture: a woman identified as Catharine of Aragon on the left and a traditional Madonna and Child on the right. Wikimedia Commons

What makes the portrait so strange is that Michel Sittow was actually a very accomplished artist. As you can see from two of his works above (one identified as Catherine of Aragon; the other a traditional Madonna and Child), he had no difficulty rendering his subject in a realistic light. Plus unlike almost every other artist of the age, he knew how to paint babies as babies, not as ugly little muscular men with baffling six-packs and receding hairlines.