So, a while ago I was chatting with an English teacher and some other people my age ish. We were talking about the 'classics' from our high school days and how a) utterly inappropriate they are for teenagers in general and b) how boring they must be for kids who don't like reading much. I think the example that was used was Catcher in the Rye which is a coming of age novel given to people not yet of age *and* in a completely different world than the one in the book. And books like 1984 and Animal Farm, or my personal favorite, Brave New World (which to me in HS was so totally a Utopia--a world where everyone knew where they were supposed to be and what they were supposed to do) are less obvious to teens than they are a few years later.
So I started making a class in my head, taking the classics, and pairing them up with contemporary books that 'match' but are more (theoretically) interesting to current teens. Surely it must be possible to look at what we expect a book to be doing and find an analog that would appeal to kids and still a) have the same message and maybe even b) help train critical reading skills.
So Brave New World pairs well with Scott Westerfeld's Uglies/Pretties/etc series. Dracula contrasts with the contemporary vampire books.
I had a few more, but I've forgotten them, and my work server is back up, so you'll just have to come up with your own.