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/don't give away any of the story!

/don't give away any of the story!"
One of my favorite books of all time! :)

Some sort of 'taste' is really required if you're going to start chipping away at that formidable (and rather ambiguous) group of books designated as 'classics'. Try and think of particular genres you enjoy (a good question is do you enjoy 'literary fiction', books that are written as artistic statements of writing-in themselves, or 'genre fiction', books written to a generic model, e.g. crime fiction); try and think of particular periods (even narrowing it down to a century will help greatly); try and think, perhaps, why you enjoyed certain books more than others beyond the merely stylistic or narrative level (i.e. considering thematics).
Any recommendation would really be a vague shot in the dark without at least some narrowing down. Going from Orwell to Steinbeck to Austen is a fun bit of discovery but there's really no continuity or connection at all; the 'classics' are still just an abstract category that you're reading 'for the sake of reading', rather than for taste or enjoyment (though you may, of course, incidentally just enjoy some of the titles you are prescribed by the canon). Be self-conscious when you read 'classic' literature and constantly question yourself why you're enjoying it (if it all) and why you were provoked to read it in the first place: in being 'well read' it is more important to be a critically engaged reader than to have simply read the clichéd top-100.
Though if I'm really pushed to recommend some titles, I would honestly start right at the beginning of the Western canon and would encourage a 'reading through' of titles that pique your interest. That is really the best way to gain an understanding and proper comprehension of literature both as an art 'form' and as a form of historical expression. Read your Homer and your Virgil and your Ovid and your Cervantes Saavedra, Miguel de and your John Milton and your Dante Alighieri and your William Shakespeare and so on. I am not exaggerating or over-estimating their importance - you will really enjoy everything that has followed much better (i.e. the allusion and allegory, the inspiration and influence, the ironising and subversion) if you are versed in the 'proper classics', per se.
Authors mentioned in this topic
John Milton (other topics)Virgil (other topics)
Miguel de Cervantes Saavedra (other topics)
Ovid (other topics)
William Shakespeare (other topics)
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