In early 1908, after the death of his mother, 18-year-old Adolf Hitler left his provincial hometown of Linz and moved to Vienna, the glamorous capital of the Austro-Hungarian Empire. Leaving behind his late father’s ambitions for him to become a civil servant, Hitler saw Vienna as the ideal place to pursue his own youthful dream—to become an artist.

But while Hitler’s childhood friend and new roommate, August Kubizek, was immediately accepted to a conservatory to study music, Hitler spent his first months in Vienna sleeping late, sketching and reading piles of books.

As biographer Volker Ullrich writes in Hitler: Ascent, 1889-1939, what Kubizek didn’t know was that before moving to Vienna, Hitler had already been rejected by the city’s Academy of Fine Arts. Though he had passed the initial exam in 1907, his drawing skills were “unsatisfactory,” the admissions committee decided.

Years later, in his autobiographical manifesto Mein Kampf, Hitler claimed that the rejection struck him “as a bolt from the blue,” as he had been so convinced of his success. In the fall of 1908, he again applied to the Academy of Fine Arts, and again they rejected him. Over much of the next year, he would move from one cheap rented room to another, even living in a homeless shelter for a time.

Then in 1909, Hitler finally began earning money by making small oil and watercolor paintings, mostly images of buildings and other landmarks in Vienna that he copied from postcards. By selling these paintings to tourists and frame-sellers, he made enough to move out of the homeless shelter and into a men’s home, where he painted by day and continued studying his books at night.

In Vienna, the frustrated young artist had become interested in politics. Though Hitler claimed in Mein Kampf that his anti-semitic views formed during this period, many historians doubt this simplified story. After all, Samuel Morgenstern, a Jewish store owner, was one of the most loyal buyers of Hitler’s paintings in Vienna. But his time in Vienna did shape Hitler’s worldview, particularly his admiration of the city’s then-mayor, Karl Lueger, who was known for his antisemitic rhetoric as much as his oratorical skills.

Hitler continued his artwork after moving to Munich in May 1913, selling similar scenes of the city’s landmarks in shops and beer gardens. Though he eventually found several loyal, well-off customers who commissioned works from him, his progress came to a grinding halt in January 1914, when the Munich police tracked him down due to his failure to register for the military draft back in Linz.

As Ullrich recorded, Hitler failed his military fitness exam and was declared by the examiners “unsuitable for combat and support duty, too weak, incapable of firing weapons.” But he would enlist voluntarily that August, after the outbreak of World War I, ending his stint as a struggling young artist.

In the decades that followed, Hitler’s formative years in Vienna and his frustrated art career became part of the myth-making—by Hitler himself and by his followers—that helped drive his fateful rise to power in Germany. As Führer, Hitler railed against modern art, calling it the “degenerate” product of Jews and Bolsheviks and a threat to the German national identity.

In 1937, the Nazis rounded up some 16,000 works of this type from German museums and put hundreds of them on display in Munich. The exhibition, intended to heap scorn on the artists, was attended by some 2 million people.

As for Hitler’s own art, he allegedly had his paintings collected and destroyed when he was in power. But several hundred are known to survive, including four watercolors confiscated by the U.S. military during World War II.

Though it is legal in Germany to sell paintings by Hitler as long as they do not contain Nazi symbols, works attributed to him reliably generate controversy when they come up for sale. In 2015, 14 paintings and drawings by Hitler fetched some $450,000 in an auction in Nuremberg. The auction house defended the sale by arguing the paintings had historical importance.

In January 2019, German police raided Berlin’s Kloss auction house and seized three watercolors said to be painted by Hitler while he lived in Munich. Though starting prices for the paintings were set at €4,000 ($4,500), authorities suspected they were forgeries.

Less than a month later, also in Nuremberg, five paintings attributed to Hitler failed to sell due to similar fraud concerns. Stephan Klingen of the Central Institute for Art History in Munich, told the Guardian at the time that authenticity is especially hard to verify in the case of Hitler’s supposed works. This is because Hitler's style was that of a “moderately ambitious amateur,” Klingen said, making his painting impossible to distinguish from “hundreds of thousands” of similar works from the same time period.