20. In Milan, it’s been illegal not to smile since the 19th century
A strange and obscure city ordinance from Milan demands everyone in the city smiles. Grumpy looks are punishable by fines, but if you’re at a funeral or visiting a hospital you’re exempt. Why you have to smile is hotly debated. The law dates to the Austrian rule of the city, so perhaps it meant to force people to accept foreign governance. That said, dissidents would presumably be harder to spot. Another theory suggests the Austrians thought a happy-looking city would encourage others to visit, settle in, or trade with Milan. Whatever the law’s origin, though, it’s never enforced today.