16. Notes from the Underground by Fyodor Dostoevsky
Face it, there is nothing more impressive than being able to claim that you have a read a Russian classic. Known for their character-rich plot density and staggering length, Russian novels challenge adults with their sheer scope. But this smaller work by Dostoevsky is shorter than most, more of a novella than an actual novel. Much like his dubious heroes in Crime and Punishment and The Gambler, Dostoevsky’s Underground Man is philosophical, thought-provoking, the perfect fodder for your teenage devil’s advocate, and no one you’d actually like to meet on the street. Your teen will come for the prestige and he’ll stay for the misanthropy. Happy reading!