If you're going to talk about great songwriters and songs then you really can't get very far without mentioning Janis Ian. It's amazing how many people don't know At Seventeen despite being nominated for five Grammy's and winning two. It is, hands down, the best song ever written about growing up outside the in-crowd. What's so amazing about this extraordinary piece of writing is that every verse is gold. If the song only contained one of the verses it does, and the rest were crap, it would still stand out on the strength of that one line. The fact that every line is dead-on target is simply amazing. Still, my favorite is this one:
To those of us who knew the pain
of Valentines that never came
And those whose names were never called
when choosing sides at basketball
If you don't know it, listen to it about 20 times and then try to think of any song in the last 30 years that describes the quiet desperation of geekdom better.
Janis Ian - At Seventeen (1975)