I had to read "Death of a Salesman" in high school (along with "Catcher in the Rye"). It was a painful waste of time. Then we had to have the usual English class discussion about "what it all means." Eurgh.
Also, The Crucible, by Arthur Miller, which is a thinly disguised portrayal of the McCarthy era as a "witch-hunt". The Catcher in the Rye is such a boring portrait of a boring loser. I don't know why we had to read it back then. But it seems kind of topical now, though. I'm sure Holden Caulfield would be tweeting his boring ass off today like all the rest of a bored and boring generation of self important time-wasters.