Nineteen Eighty-Four by George Orwell.
The best book George Orwell ever wrote was Down and Out in Paris and London. I once got into a fist fight defending the validity of this statement. Well, I guess it was more just a bunch of girly slapping, but whatever. Nineteen Eighty-Four was groundbreaking in its time, and in many ways its cautionary depiction of a state-controlled dystopia shows remarkable foresight, and a well-honed, dramatic writing style. Nevertheless, it sucks. And Aldous Huxley kind of did the same thing with Brave New World, but slightly better. And, you know, first. Down and Out is definitely Orwell’s magnum opus.
On the Road by Jack Kerouac.
Truman Capote once said of this classic Beat novel, “That’s not writing. It’s typing.” But then again, Capote wrote Breakfast at Tiffany’s, so what does he know? Actually, that book is also somewhat overrated, although admittedly it’s the inaccurate film adaptation that is inexcusably overrated: WHAT IS WITH MICKEY ROONEY AS MR. YUNIOSHI???

WHUT??? Anyway. On the Road is actually a pretty good book. I just have real difficulty believing people who are all “omg it like, changed my life.” All it did to me was make me think in nonsensical run-on sentences all day, which is really not that much of a change at all.
Catcher in the Rye by JD Salinger.
Holy shit, was Holden Caulfield the first ever emo kid or what?! I have a theory that anyone who loves this book read it whilst in the grip of teen angst. Which is alright when, you know, you’re an actual teenager, and much less excusable post-pubescent blues. If I wanted to read some kid whinging about “lousy phonies”, I could just log onto Livejournal. The prose would arguably read better.
Crime and Punishment by Fyodor Dostoevsky.
Actually, I think I just read a really shit translation of this one, and consequently did not get further than halfway. Nevertheless, a lot of people who just want to sound real smart tend to cite this as one of their favourites, and it is therefore overrated. Indubitably.
Like, pretty much everything written by Chuck Palahniuk.
There’s controversial writing, then there’s writing that is trying to be controversial. (Was that meant to be ironic?) We get it, Chuck: you’re nihilistic and anti-establishmentarian and eminently knowledgeable and ooooh-ever-so-fucking weird. If you’ve already seen the Fight Club movie, read his short story Guts here, and you’ll basically be a bona fides Palahniuk expert. Just like everyone else.
(DISCLAIMER: I actually really like these books. I just think they’re overrated. But hey, my favourite book of all time is Catch-22 by Joseph Heller, and I don’t even know how many times I’ve read the Harry Potter series, so my opinion is positively moot.)