In 1696, William III introduced a tax which required those living in houses with more than 6 windows to pay a levy. To avoid this, house owners would brick up all windows except 6. As the bricked-up windows prevented rooms from receiving any sunlight, the tax was known as daylight robbery. (Source)
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In 1698, Peter The Great introduced the “Beard Tax” after he visited Western Europe and liked their fashion sense. Anyone with a beard was forced to pay tax for it, and in turn given a beard token. If you were stopped by the police without the token they would immediately shave your face on sight.
Hitler was a chronic tax evader, and was even fined by his own government over it in 1934. He then got the tax department to declare him exempt from taxation.
Photo : German Federal Archive / wikimedia
Most Converse sneakers have a very thin layer of felt applied to their soles, in order to legally classify them as slippers. This saves the company more than 33% in import tariffs.
Monowi is a town of Nebraska that has a population of 1, the Mayor pays taxes to herself.
Denmark charges a tax of 150-180% on all new car purchases.