The first one is easy. It's on the playlist for StT, because it perfectly describes Mira:
Simon & Garfunkel's "I am a Rock."
The Beatles, "Hey Jude"
Janis Ian, "Seventeen"
The Carpenters, "Rainy Days & Mondays"
Billy Joel, "Vienna" (which did wait for me--I spent a glorious academic year there in 1984-85.)
If I were a teenager today, these would be my two favorites:
Carbon Leaf, "What About Everything"
Indigo Girls, "Love Will Come to You"
What were your sad songs when you were a teen? Let Sarah know at http://sarahockler.com/blog/ and let me know in comments.