To Roman emperors, statues were colossally important things, not just for their own egos but for keeping power across the vast Empire. Most emperors were venerated as gods after their deaths, and "imperial cults" who worshipped them posthumously were a key part of unifying disparate parts of the empire.

Perhaps nobody understood this need for a grande resemblance more than the Emperor Augustus, one of the most powerful leaders in Roman history. And the most famous statue of him is just completely bonkers.

The Prima Porta, as it's called, is currently in the Vatican Museum in Rome, and shows Augustus, who was described by the biographer Suetonius as quite short with bad teeth, as colossally tall with enormous, well-proportioned muscles. (Suetonius, writing many centuries after Augustus's death, also mentions that Augustus was "unusually handsome", but it's unclear whether that was the truth or just a product of the many handsome portraits made of him.) The maddest part of it, though, is that a tiny Cupid is hanging around his ankles, cheerfully riding on a dolphin. This was meant to remind people that Augustus claimed to be directly, personally related to the goddess Venus, Cupid's mother, and the legendary founder of Rome, Aeneas. Yes, really.

What looks, on first observation, like an extraordinary work of narcissism (does any leader really need to show everybody what he looks like on all sides?) is in fact a demonstration of the power of opulent, ridiculous art across two mediums. This portrait of Charles I, known as the "triple portrait", was painted by Van Dyck, who, according to British art historian Sir Keith Thomas, defined the entire era of the 1600s in Britain via his court portraits: his "images of regal majesty, gilded youth and feminine beauty... evoke an age of sumptuous costume and cultivated ease". This particular portrait of Charles I, though, wasn't necessarily designed to be on display; it was actually to be sent to the sculptor Bernini in Rome, to allow him to make a bust of the king (who could, of course, not be bothered to sit for the bust himself). Hence the fact that the king is wearing different clothing and earrings in each of the three: he and Van Dyck wanted to give Bernini options!

Famously, however, Bernini was unimpressed. "Never have I beheld features more unfortunate," he said when he received Van Dyck's elaborate portrait. The resulting bust was a failure in its aim, too: it was meant to convince Charles I to rejoin the Catholic Church, but that never happened. Charles was executed, and the bust itself was destroyed by fire at the end of the 17th century. All those hilarious clothing changes for nothing.

Yes, this man is deliberately looking ridiculous. Yes, he was also the Holy Roman Emperor Leopold I. A member of the Hapsburg family, which was famously ugly through centuries of aristocratic inbreeding, Leopold I wanted his legacy to be preserved as a patron of the arts, and so commissioned this hilarious image from the painter Jan Thomas, who specialized in depicting royalty doing incredibly odd things (his portrait of an Austrian prince taking part in an "equestrian ballet" in 1667 shows both the prince and the horse wearing monumentally stupid hats).

Leopold I is here wearing the costume of the character Acis from the opera "La Galatea". He was a famous opera-lover, staging huge productions for birthdays and weddings, and Acis and Galatea, characters from Greek mythology, were hugely popular as subjects. Oddly, Acis was a humble shepherd and his lover Galatea a tragically murdered sea-nymph (Leopold's wife, Margarita Teresa, wore a similarly opulent ensemble in a matching portrait as Galatea). Whether you get "humble shepherd" from this outfit is severely debatable. It's probable that Leopold just wanted to wear something with impact, and didn't really understand subtly.

The first portrait commissioned by Napoleon after becoming First Consul of France would become one of the most famously, ridiculously extravagant in art history. His clashes with the portraitist, Jacques-Louis David, are legendary. David wanted at first to picture Napoleon in battle with a sword, but Napoleon retorted that battles were no longer fought that way, and that he wanted to be shown looking grand on the back of a horse. He also point-blank refused to pose, telling the painter, "No one knows if portraits of great men are likenesses; it suffices that their genius lives there." David's own son had to pose in the correct regal gear on top of a ladder to approximate the leader's pose.

The image of Napoleon "calm on a fiery horse", in the eventual Emperor's own words, became one of Napoleon's favorites; he commissioned several copies of it and five currently exist. He was likely particularly flattered by the fact that David wrote his name alongside those of Charlemagne and Hannibal in the rock of the mountain. "We would never know," notes one art historian drily, "that the general did not, in fact, lead his troops through the perilous St Bernard Pass and up over the Alps himself, but rather followed them the next day on a donkey." Napoleon would have further adventures in ridiculous artwork - Ingres' image of him, "Napoleon On His Imperial Throne", in 1806 was so over-the-top in its references to Zeus and immortality that contemporary critics loathed it. The David portrait, though, has entered art history legend.

The Fascist political rise in Italy in the 20th century inspired, and was fuelled by, a movement called Futurism in art. It was all about embracing the new, the modern and the technological, and in its first manifesto in 1909 it also declared war "the world's only true hygiene": a clear fit for Fascist military masculine ambitions. It's from Futurism that we get some of the most fascinating, disturbing images of Fascist-era Italy, including this infamous image of Mussolini's face superimposed grandly on a view of Rome.

The artist, Alfredo Gauri Ambrosi, isn't widely known aside from this picture, but he was part of a phase inside Futurism that was known as "aeropittura", or using new flying technology as the central theme for art and images. The placing of Mussolini's famous face over Rome was a clear political statement; we don't know if Mussolini himself commissioned the painting or if Ambrosi was simply inspired by his leader, but it's an imposing image of what the Futurists, and many other Italians, thought of him: as the very center of their world and the definition of Italy. And yes, it is meant to terrify the sh*t out of you.

Dictators are among the most highly aware of the power of artistic portraiture to depict their majesty and deploy propaganda messages. They also have high levels of artistic control, and nowhere exemplifies this better than North Korea, which has been producing high-quality, devotedly flattering, completely bonkers images of its dictatorial leaders for decades, often in gigantic murals. They're doing things as diverse as cuddling children and supervising film shoots. This image surfaced most recently in the work of the artist Chris Rellas, who takes famous art and alters it to contain elements of consumer culture (he put Kim Jong Il in a Prada coat), but like most propaganda art out of North Korea it's of uncertain lineage or date. It does, however, exemplify just how insane propaganda portraits can be.

The deeply jarring thing about this image, in case you haven't noticed, is that everybody is cheerful, apple-cheeked, and leading a battalion carrying nuclear warheads. The central figure of Kim Jong Il himself is the point: he's leading North Korea happily into a militant future, clad in all-white. The other vaguely sinister aspect is that there is one unidentified gentleman behind him who is not smiling. If this was, as is entirely possible, a public rebuke to a North Korean political enemy, it was probably a terrifying one. Compared to this, Trump's TIME portrait looks like a piece of gentle hubris.

Turkmenistan's president Gurbanguly Berdymukhamedov made headlines in 2015 when he erected a statue of himself riding a horse in the capital, Ashgabat. Not so unusual in the grand scheme of political portraiture, one might think - horses have been a favorite theme of male leaders since ancient Greece - but Berdymukhamedov's was on top of 20 meters of white marble, cast in bronze, and covered in 24 carat gold leaf. The cost was not mentioned to the international media, but what's even more interesting is that Berdymukhamedov was actually only following precedent. His forebear as Turkmenistan's leader, Saparmurat Niyazov, erected a gold statue of himself that rotated as the sun crossed the sky (and which Berdymukhamedov has now moved out of the central city).

The president is an image-conscious showman; ahead of the (largely irrelevant) elections in February, which he won with 97 percent of the vote, the Guardian reported that he was depicted singing to workers and on TV playing a Justin Timberlake song to an adoring crowd. However, while the horse itself in the statue is reportedly the president's favorite, one of Turkmenistan's Akhal-Teke breed, photographers accidentally captured him in 2013 spectacularly falling off a horse, in a race that the state news then reported that he'd won. Horses are key to his image, but not perhaps in the way he had anticipated.