Lewis Carroll’s fair-haired heroine is not your typical seven-year-old. She’s polite, precocious, quick to show off her knowledge. She’s well-mannered, though put off when others aren’t. Last and perhaps most importantly, she’s wildly curious, which serves her well on her surreal and psychedelic explorations in Wonderland. Here’s the thing: Carroll’s stories may be for children, but they are also quite dark and strange, and any playlist worthy of Alice Liddell must reflect that. So press Play and join us on a musical adventure for Alice.

Yeah, he just got kicked out of prep school, but this seventeen-year-old is smarter than he gives himself credit for. And okay, he’s judgmental and cynical, and the list of things he has contempt for is never-ending, beginning with grown-ups and phonies. Nevertheless, despite his prickly nature, he’s also honest, vulnerable, and protective of what little innocence he sees in the world. Holden Caulfield has become a poster boy for teen alienation, which is something he’d probably hate. In honor of the original Mr. Misunderstood, here's a playlist to cultivate one's disillusionment.