Ender's Game was terrible.
The Road as was previously mentioned.
Since he likes science/math - The God Delusion by Richard Dawkins.
A Confederacy of Dunces, perfect book to read IMO.
We had to read Of Mice and Men, Brave New World and Mary Shelley's Frankenstein when I was his age.
If he finds reading "dull" and is about to go off to college though, I'd say he's got bigger fish to fry than trying to find a few books he might be interested in.
Edit: I liked The Great Gatsby around that age, as well. Most of the stuff I read is fantasy/sci fi, though.
So I should have proofread my post, oh well.
If he's interested in History, The Red Badge of Courage should suffice.
I would agree with others that suggested Stephen King. Most of his books are pretty solid picks for boys that usually don't like to read, if you're not worried about focusing on the classics. Heinlein's Starship Troopers might be good too. I know you mentioned he's not into scifi, but the book itself is more about the military training than anything else (even though I love the movie, it is absolutely NOTHING like the book. like not even close. movie was definitely just a "lets put Heinlein's name on it and name a few characters the same so people will be interested")
If you want to make sure he's reading "11th grade" material, then I have to agree with the above and avoid Ender's Game. I love that book too (have most of the series signed by Card), but it really is 6th-7th grade material. If you're trying to just get him into something, then I say give it a shot because it is a great read.
You could always try the Odyssey and/or Seamus Heanley's Beowulf. They're a little more challenging, and may not interested him as much. But they are classics and less girlie than something like Pride and Prejudice.
Dante's Inferno. If people being tortured left and right/mythology doesnt appeal to him then all hope is lost.
Are Stephen King books really considered "literature"?
I dont say that to be smug, I mean it in the way that the mother wants him to be able to do literary criticism; I don't think King will fly at the University level.
Yeah... I'd avoid King. It's pseudo-horror on about the same reading level as trashy romance novels. Completely agree about the filler, too. He publishes 900-page novellas.
We're trying to get a kid who doesn't like to read to enjoy reading. Stephen King's books are accessible and in the cases of the books I recommended, can be read in under a weekend. It's definitely what I was reading before shakespeare entered my life, and without it I probably wouldn't have touched stuff like Hemingway, which few high schoolers are equipped to read on anything but a superficial level.
And I know if you wanted to come off as a smug know it all you would at least have suggested he read the Divine Comedy rather than merely the first third of it.
Fucking haters. I have a plethora of King novels, and about 20 first editions. Comparing "The Stand" and "The Dark Tower" to trashy romance novels is fucking ignorant.
The Divine Comedy is only fun when people are getting the shit kicked out of them. (eh just kidding I like the whole thing)
I agree with what you said about needing an introduction, as I read a lot of King/Saul/Crichton growing up. But we're talking about someone who is 16 though and is obviously being prepped for some form of advanced schooling. I think a better plan would be to actually introduce him to books that are recognized as "scholastically acceptable" (cant think of a better phrase), that may appeal to his interests.
Unfortunately, a lot of stuff I read I'm sure would bore him to death.
Speaking of Crichton, Sphere was the first novel I read, and it was great. Good starter book.
My Freshman english class had to read Ender's Game and the script from Quentin Tarantino's Inglourious Basterds this past semester.
I think people are overstating the amount you need to know to actually get through early classes. I think the longest thing we had to read (in my english class) was 60 or so pages and we were given a week to do it.
...kids these days.
His interests probably won't be well revealed by shoving the western canon down his throat. You gotta give him low-difficulty books that cover a lot of bases, then observe his expressed interests AND THEN see what part of canonical literature aligns best with it.
Here are a few suggestions that I think would work well.
Douglass Coupland - Microserfs. Generation X. Life After God.
James Morrow - This is the Way the World Ends. Towing Jehovah.
Neal Stephenson - The Big U. Anathem.
Walter M. Miller - A Canticle for Leibowitz.
John Kennedy Toole - A Confederacy of Dunces.
Julian Barnes - A History of the World in 10 1/2 Chapters. Talking it Over.
Matt Ruff - Gas, Sewer, Electric. Fool on the Hill.
I think the big problem here is, he's going not going to connect to lit without liking to read first. There was a lot I didn't appreciate about of The Great Gatsby when I first read it because I was at a point when I didn't really like to read anymore. Once I found myself liking to read, rereading Gatsby and eventualy The Tale of Two Cities actually allowed me to understand what I read, enjoy it and thus analyze rather than reading only to cherry pick the test questions with what I thought would be the buzzwords. Sure you can force "certified lit" down his throat, but if you really want him to be able to analyze well, he needs to be able to enjoy it for what it is.
Howard V. Hendrix might interest him. Science Fiction but not campy shit like Orson Scott Card. Don't let him read The Catcher in the Rye either, shit's fucking horrible in my opinion.
If the better course of action is to get him to like reading first, I'd also have to recommend Palahniuk's Survivor. And a lot of his other stuff, as long as it isn't Diary.