I was reading Ian Fleming, Arthur Conan Doyle, and some of Stephen King at that age. The Shining was required reading when I had to retake Freshman English.
I wouldn’t recommend Dandelion Wine, actually. Every single teenager I know(and seeing as I go to school with them, I know many) hated that book. It may have good themes and whatnot, but it is boring. as. hell.
I’ll echo some others when saying Stephen King. The Shinning or Pet Semetary would keep him occupied. I also recommend Fight Club by Chuck Palahniuk, Animal Farm by George Orwell, and The Perks of Being a Wallflower by Stephen Chbosky.
I first read John Irving’s “The World According to Garp” when I was 16.
Some fun reading would be anything by Carl Hiaasen. “Tourist Season” and “Skin Tight” in particular. And since all of his books are set in Florida that could prove interesting to him.
Oh yeah, and I was about 16 when I first read The Hitchhiker’s Guide to the Galacy. Some of Alan Dean Foster’s work is in a similar vein, Glory Lane for example.
One summer when I was 16 or 17, I read a whole pile of old Ellery Queen mysteries. In the fall, I tried to get my English teacher to accept some of them as “summer reading” books. She wouldn’t consider even counting the whole lot of 'em as one book. Fortunately they weren’t the only books I’d read. . .
My favorite book from that time, though, was the massive THE PEOPLE’S ALMANAC by David Wallechinsky and his dad, Irving Wallace. It’s still on my book shelf with other volumes the Wallace/Wallechinsky clan came out with, THE PEOPLE’S ALMANAC 2, The Book of Lists, THE PEOPLE’S ALMANAC 3, The Book of Lists 2, Significa, etc. I just couldn’t get enough of that nonfiction trivia.
I’d reccomend the Mad Scientists Club books, John Christopher’s The Tripods Trilogy, and Jack Kelly’s Gunpowder. (The last one is non-fiction, and you can guess what it’s the history of. Facinating stuff, that.)
You might also try Gibson’s The Difference Engine (alternature history, about the computer revolution sparked 100 years early by Babbage’s mechanical “analytical engine” computer.), and Alan Moore’s graphic novel Watchmen, which is fantastic and engrossing.
I’ve never met a kid (or anyone for that matter) that didn’t like Ender’s Game by Orson Scott Card.
I also read it as a teenager, and it was one the best novels I have ever read.
The Tracker by Tom Brown (although he might want to remain skeptical about the authenticity of some of the characters)
A Prayer for Owen Meany by John Irving (My granddaughter introduced me to this one; it’s on my top five list. Parts of it are unbearably hilarious.)
Another vote for Ender’s Game and the Hitchhiker’s Guide series.
I remember really enjoying Jurassic Park when I was about that age, and you can probably find that in any second-hand bookstore. Ditto any John Grisham or Wilbur Smith. I can’t stand them now, and they’re not very ‘good’ books, but if he’s not a terribly critical reader (and god knows I wasn’t at sixteen) he’ll probably enjoy them. Comic strip collections, like Calvin & Hobbes or The Far Side might be good - I can read in cars, but I never like to read anything too heavy.
How does he feel about modern classics? Catcher in the Rye or A Clockwork Orange are both pretty engrossing, as are 1984 and A Brave New World.
I had forgotten about these (although they are all on the shelf behind me). I also read them (at least the first 2) when I was around 16 - 18 – when they first came out. Very good reading and full of interesting stuff, if your son enjoys that sort of thing. My own boy likes non-fiction, but not the randomness of the big trivia style books – he never read any of my People’s Almanac / Book of Lists stuff, except for dribs and drabs that he’s look up in the index. My nephew on the other hand, at about 16, got ahold of my Straight Dope books (how did we all forget those?) and ate them up, then moved on to the rest of my trivia shelf and just plowed through it. Other recommends in this genre include anything by Charles Panati.
Also, in a slightly different vein, the three Big Secrets books by William Poundstone. I’ve seen these in an omnibus version at Barnes and Noble on the bargain shelves, BTW.
Robert E. Howard’s Conan The Barbarian series.
Just the thing for a teen!
no, he’s at the age where he wants to learn about women. I suggest ‘The Story of O.’ 
I was a huge Hemmingway fan at that age and I was just starting to get into Salinger. My first Salinger book was Franny and Zooey. I wouldn’t recommend starting with Catcher in the Rye. Its’ Salinger’s most popular work, but not his best. FaZ is a good intro to Salinger’s style and a fun, quick read. As for Hemmingway you can start pretty much anywhere, except for the later works. With the exception of The Old Man and the Sea they suck.
Don’t know how you feel about comics, but there are some pretty good manga (translated Japanese comics) and graphic novels out there too. There are also comic strip books. Fox Trot is amazing.
Any and all of the Hornblower novels. Tell him he cannot be Hornblower. I am Hornblower.
How about Alas, Babylon by Pat Frank? It is set in Florida. It might also end up being required reading for school.
Personally, I enjoyed Alas.
Personally, I hope it becomes a forgotten book, that people shall scratch their heads over in blank bewilderment, 50 years from now.