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Saint Petersburg is no longer Russia’s capital, but it’s still considered its cultural center. Designed from the very beginning as a symbol of modernity, industry, and progress, the city can still be seen as one big monument to the Russian monarchy. But its artists have never fallen in line, rebelling against the aristocracy and putting the very idea of progress into question.

From humble beginnings to cultural epicenter

Saint Petersburg was founded in 1703 near the River Neva, on a patch of swampland where no one in particular had ever lived. Within a few decades, it was one of the largest cities in Russia. It was named Saint Petersburg for its conqueror’s patron saint; then Petrograd, to sound less German; then Leningrad, in honor of another beloved strongman; then, nearly three centuries after its founding, Saint Petersburg again. It was supposed to be a symbol of the Enlightenment, but it was mostly built by slaves, tens of thousands of whom froze to death before it was finished. Dostoevsky called it the most deliberate place in the world. He also called it, “that rotten, slimy city.”

Saint Petersburg has always worn its contradictions on its sleeve. It has also been, almost from the beginning, a city of artists. Throughout the 18th century, Russian monarchs lavished obscene sums on Saint Petersburg’s culture. They paid the best Italian architects to design grand promenades and churches, sent thousands of the country’s best painters to the Imperial Academy of Arts, and stuffed the Hermitage Museum with Rembrandts and van Dycks. (Much of this was done through Empress Catherine the Great’s acquisitions from the Berlin merchant, Johann Ernst Gotzkowsky, including Danaë from 1636, above.)

A lot of the art to come out of Saint Petersburg can be interpreted as an advertisement for Russia itself, a way of announcing the country’s arrival as a great cultural power—and a great power, period. But some of Saint Petersburg’s greatest artists have taken a more skeptical view of things, never forgetting the rotten swamp beneath their perfect city.

The (double-edged) masterpiece of the 18th century

At first glance, Karl Briullov (1799–1852)—the first internationally renowned artists to be born, raised, and educated in Saint Petersburg—seems to be glorifying his motherland. But a closer look reveals more. His most famous canvas, the massive, apocalyptic The Last Day of Pompeii (1830–33), put Russia’s nascent art scene on the map. (It also transformed him, in his mid-thirties, into a celebrated figure.) And yet, Pompeii is anything but jingoistic. The great Saint Petersburg writer Nikolai Gogol wasn’t alone in seeing the work as an ambivalent metaphor for the city. Less than a decade earlier, floods had killed hundreds of its residents, a reminder that Russia’s proudest, chicest city was no more immune to nature than Pompeii had been. Something similar can be felt in many of the great works about Saint Petersburg: a creeping fear that, no matter how impressive the city grows, it could be swept away as abruptly as it was created.

While an artist like Briullov (or Gogol) might highlight the terror of such a precarious civilization, some of Saint Petersburg’s other great painters turned it into something positive. Out of the many popular artists to emerge from the Imperial Academy in the second half of the 19th century, a sizeable chunk were landscape painters who portrayed the natural world with affection. Ivan Shishkin, who graduated from the Academy in 1860, spent a quarter-century teaching landscape painting to Saint Petersburg pupils, but preferred to live outside the city in the company of his favorite subject—trees. In the work of Arkhip Kuindzhi, nature seems like a benevolent god. Compared with Briullov’s Pompeii, Kuindzhi’s Red Sunset on the Dnieper (1905-08) is downright tranquil—the wrathful glow of Mount Vesuvius versus the radiant warmth of the sun.

The avant-garde, washed away by revolution

Late in his life, in 1897, Kuindzhi was fired from his Saint Petersburg teaching post for supporting student protests. For that matter, Saint Petersburg at the turn of the 20th century was brimming with radicals of all kinds, and many of these radicals saw avant-garde art as a crucial part of political revolution. The modernist painter Marc Chagall only lived in the city from 1906 to 1910, but his time there would color his work for decades to come. As late as 1942, he was still sketching glorious, gravity-bending views of its bridges and buildings. Chagall, a Jew, left Saint Petersburg partly to escape the bigotry that was typical of Russian society at the time. Like so many of his fellow avant-gardists, he welcomed the Bolshevik Revolution of 1917 partly because he thought it meant the end of Russian anti-Semitism.

We know what really happened. The government Chagall had supported turned out to be more intolerant than any czar. During World War II, Saint Petersburg (Leningrad at the time) lost more than a million lives to starvation; after 1945, the city was quickly repopulated, but there was no replacing its culture. The avant-garde that had once attracted artists from around the world was smothered in state-sponsored kitsch.

If there’s a single artwork that can sum up Saint Petersburg’s relationship with the arts, it may be the tower Vladimir Tatlin designed to commemorate the 1917 Russian Revolution. 1300 feet tall, and made of glass, iron and steel, it was meant to dwarf every other structure in Saint Petersburg (Petrograd at the time) and be as inseparable from the city as the Eiffel Tower from Paris. How appropriate of Saint Petersburg, with its dazzling inventiveness and botched utopianism, that the tower was never actually built.