Now I'm approaching middle age. Last year I was looking for books to read in a language I'm learning. I decided to re-read Catcher, and to my surprise, found it heartbreaking. I mostly remembered the plot, but it was a completely different book to me as a man than as a boy.
Everything Holden does is in the shadow of his grief over his dead brother. As a kid, that flew over my head. I couldn't have understood the hole in your heart that comes from losing someone you deeply love and admire. I didn't get the sad chain of cause and effect - there are hints at how it affects everyone in his family.
It's a beautiful and subtle book, and it rewards re-reading later in life.