I only finally read 1984 about a year ago. Everyone should read it: it's a great combination of entertainment and insight; funny, yet terrifying. The classics don't always live up to the hype, but there's a reason so many terms from the book ended up in our vocabulary.
1984 is on my list. I just finished "Brave New World" by Aldous Huxley and although it was a very good read, it was a little depressing since I could imagine the future turning out that way.
Everyone fears big brother, and the term 'Orwellian' became a oft-used word to describe the oppressiveness of an overt totalitarian power.
Huxley wrote about our being lulled into submission through indifference. 'Huxleyian' never became a common term, because we apparently are indifferent about a world in which people are indifferent.
I'd also suggest Fahrenheit 451 and A Clockwork Orange, which make great reads. All these novels are part of the 'dystopian' genre, but the two you mention are likely the most famous.
It's a pretty dark form of humour, I guess. I found Winston to be quite comical character himself, which I think makes the book easier to endure in the darker parts. The extremity of some of the scenes/ministry policies and other characters made them both comical and scary. The former because they seem ridiculous, the latter because you feel it is not actually outside the realm of possibility (when you think on modern history).