Anything Nabokov - especially Ada, Lolita, and Speak, Memory. Just beautiful, beautiful, beautiful. Such incredible skill in his craft - and you can tell he’s having fun showing off too, but you don’t frigging mind because he’s just so. damned. good.
Also, not sure if this counts (if it doesn’t, it damned well should) but Gabriel García Márquez’s One Hundred Years of Solitude should be compulsory reading in all high schools.
No! Then you’ll have people saying it sucks just because it’s a book they “have to read for class”. I don’t want my favoritest book of all time being trashed! 
[sub]I did my senior thesis for Humanities on Gabriel Garcia Marquez. I luff him![/sub]
Count me as another that absolutely hated literature in hs/college, but came to appreciate it on my own time. Also, count me as another who absolutely detests reading Dickens (though, I do read A Christmas Carol every couple of years at Christmas time).
I was Jesuit educated, and then a classics minor in college, so I’ve read The Iliad, Odyssey, and Aeneid just about every year for 8 years.
I read This Side of Paradise, and The Great Gatsby every year or so, though they push the limit of ‘classics.’
I re-read The Odyssey last summer and am working my way through all of Austen’s books for the second or third time.
All of the previous posts have talked about works of fiction, but the OP asked about “classics,” so I’ll mention Galileo. Almost all of his writings are interesting and witty, and all are far more accessible than similarly seminal works from, say, Aristotle or Newton.
Most are written in the form of dialogs in which the accepted (and mostly wrong) “wisdom” of the day is defended by the bumbling Simplicio and Galileo’s new ideas are presented by the wise Sagredo. What I find most exciting about Galileo is that you can watch as he invents the modern scientific method, and overthrows the previous practice of science, which generally amounted to looking up what Aristotle had said about the subject and accepting it without question.
My recommendations: Dialog Concerning the Two Chief World Systems, which deals with the Copernican model of the solar system and sparked his fatal controversy with the Catholic Church. And if you’d like to read one of the best explanations of exactly why religion and science aren’t in conflict, read his Letter to the Grand Duchess Christina. (I personally like Stillman Drake’s translations.)
If you’re looking for a good biography of Galileo, I found Dava Sobel’s Galileo’s Daughter to be excellent.
Oops. Salvatio presents most of Galileo’s ideas, not Sagredo. (I keep mixing them up.)
I just started getting into Thoreau. Walden is a great book.
and Ralph Waldo Emerson (all of it)
JJ Rousseaus “Confessions” was good too.
With those three in mind, where a good place to turn next?
I’ll agree with Bposad about just about anything Twain wrote. Especially A Connecticut Yanmkee in King Arthur’s Court and Life on the Mississippi.
I’ve lost count of the number of times I’ve re-read The Iliad and ** The Odyssey**.
The dialogues of Socrates that Plato wrote ar priceless.
By far the most modern “ancient” writings I’ve read are the works of Lucian. Get the Penguin translation – it’s priceless.
I have a weakness for epics. I’ve Read and re-read:
The Epic of Gilgamesh
Beowulf
The Argonautica
The Rime of the Ancient Mariner
I love Austen’s books, especially P&P and Persuasion. My copy of Three Musketeers is about to fall apart. And I love reading The Raven on stormy nights.
Does Anne of Green Gables count as a classic? ::wondering::
I, too, recommend One Hundred Years of Solitude by Gabriel Garcia Marquez. It’s only about 50 years old, but if it isn’t already considered a classic, it definitely will.
The Iliad and the Odyssey have been mentioned. For another classic, try Plutarch’s “Roman Lives” (there’s also “Greek Lives”); it’s a bit dry but quite interesting.
I’ve been on a Russian Literature kick the past few years. Anything by Tolstoy (“War and Peace”, “Anna Karenina”, etc), Dostoevsky (“Crime and Punishment”, “The Idiot”*, etc), Anton Chekhov (short stories and plays), Mihail Bulgakov (“The Master and Margarita”), Boris Pasternak (“Doctor Zhivago”), etc. Dostoevsky is one of my most favorite authors, but it’s not necessarily for his style. I find his style a bit difficult to read, but the story he tells and the themes he uses are what I love.
Dammit, I forgot my asterisk:
I just finished Brideshead Revisited a couple weeks ago and it’s fantastic. I had no idea how much I was going to like it, although it’s a little too modern to be what I’d usually call a “classic.”
The Age of Innocence is I think Edith Wharton’s finest and most easily accessible novel. The movie’s also very good even if Michelle Pfeiffer is grossly miscast as Countess Olenksa.
I enjoy Dickens, but I’ve never tackled one of his really long works. The thing that I found challenging at first but have since come to really love is that every sentence is sarcastic, until there’s one that isn’t. Not something you see these days.
–Cliffy
I also like Tolstoy’s short stories.
And I’ve read Churchill’s 6 volume History Of The Second World War.
Actually, I find myself reading The Confidence Man every few years. It goes extremely well with Huck Finn. They both have that “goin’ down the Mississippi, exposin’ the hypocrisy of 19th-century American society” motif. Seriously, though, that was, IMO Melville’s greatest book. Also try White Jacket, another great Melville novel. And don’t forget the neglected The Good Soldier by Ford Madox Ford. This is a Modern classic, but in the past forty years it’s almost completely disappeared the culture.
The Canterbury Tales by Geoffrey Chaucer
The Legends of Good Women, also by Chaucer
The Consolation of Philosophy, Boethius
Beowulf, as translated by Seamus Heaney
Sir Gawain and the Green Knight
The Divine Comedy by Dante. I love the Dorothy L. Sayers translation of The Inferno, if you can find it.
Paradise Lost by Milton
Those are a few of my favorites.
Is Naked Lunch considered a classic yet? If it isn’t, it will be in a few years. Burroughs is dead, after all.
I read a lot of Poe and Lovecraft when I was younger. (Big surprise, I know. ;)) King simply cannot stand up to them, but King can’t stand up to anyone who’s not sold in drugstores. I will always love Poe’s “The Black Cat” and “The Pit and the Pendulum”, but then doesn’t everyone? Dark, overgrown 19th and 20th century horror never managed to frighten me, but I love it just the same.
I love short fiction more than most novels. I have a special place in my heart for Saki, aka H. H. Munro, and O. Henry, aka William Sydney Porter. Ambrose Bierce, W. Somerset Maugham, Jack London, and Conrad Aiken are all masters of the form, but even authors as wordy as Melville can pull it off. (“Billy Budd” is heavy-handed in its symbolism, overtly Transcendental in its philosophy, and utterly successful despite those handicaps.)
If you enjoy short fiction as much as I do, hunt out Tellers of Tales, a short fiction anthology edited by W. Somerset Maugham. I have a classic edition, much faded on the cover but perfectly readable on every page, copyright 1939 and probably printed not much later I picked up for a song at a since-closed used book store. Amazon doesn’t appear to have it, but used book websites do.
I liked Custom of the Country better.