I read both twice, once in high school and again a few years after I graduated (this was over 15 years ago). I loved The Great Gatsby even more (that opening first page is magnificent), and couldn't help but feel like The Catcher in the Rye as being so incredibly naive and juvenile. The latter experience is similar to reading (or watching) Fight Club and thinking Tyler Durden is a hero of sorts and something to aspire to, which is not the ultimate lesson.