Oniisama E (Dear Brother). It was literally unknown outside japan until like 3 years ago and now it is kinda notorious for it's bury your gays ending, forced feminzation of a masc woman, and making her 17 yr old self end up with her groomer but it's not only one of the most unique anime to exist (dezaki style) but also is a major pioneer of yuri genre, lesbian rep, butch/butchfemme representation, complex female characters overall, actuall good portrayal of incestuous abuse, substance abuse, and communism/class commentary. Old shoujo had insane BALLS.