Some dude made a list (via Cynical-C) of the "top 10 books about the darker side of adolescence".  I've read Lord of the Flies (his #1) and maybe Catcher in the Rye, as well as several others that didn't make the list. 

The problem with adolescent books is that schools force kids to read them.  And I don't think an adolescent can fully appreciate a book written about him/her until he/she is no longer an adolescent.  Maybe it's just me, but I developed a hatred of reading by being forced to read books I didn't understand (granted, I have a documented reading comprehension deficiency).  But when I look back on it and re-read some of the "classics", I'm amazed at how much truth and wisdom is contained in their pages.  I compared an incident in high school with the Lord of the Flies after realizing (again) that human nature has a tendency towards evil.  Some of the books I read in high school had such an amazingly clear message in them, yet their meaning and applicability were lost in the heyday of high school life, memorizing chemistry formulas, playing stupid sports, joining clubs that would "look good on my transcript", and (very infrequently) dating bimbo girls.  I wish somebody told me, "Grow up first, then read about what was happening while you were growing up.  It'll make so much more sense later.  Plus, you can't do anything to change what's bound to happen anyway." 

In conclusion, fake your way through high school, go to a big state college, and learn everything about life when you're ready and able.  My childhood was corrupted by a forceful compression of perceived knowledge.