Great article in the New York Times – Children’s Authors Who Broke the Rules (Sendak, Silverstein, Geisel).
There are other, older examples of outrageous books for children (Brothers Grimm, Struwwelpeter, etc.) but in the “modern era” (ie. 1900s onward) it’s still pretty rare to find picture books with challenging material. Particularly in North America. Judy Blume and Roald Dahl dished the dirt to older kids, but everyone is extra careful about the content given to pre-readers in picture books.
Currently there are a lot of out there picture book authors, but not many as thoughtful, deep and profoundly rebellious as these three. (Depicting a same-sex couple – human or penguin – may get you banned in many states, but it’s not exactly intellectually daring.)
Coincidentally I just took Sendak’s Outside Over There out of the library yesterday. Looking forward to reading it – review to come soon!