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Lolita (book; 1955)
By Vladimir Nabokov
I never got around to reading the classic Lolita until my mid-thirties, and I'm glad it took so long, because it let me appreciate the novel more for what it actually is -- not just a salacious tale of underage love (although it's that too), but also a darkly funny look at the then-new world of the American highway, and of all the soulless look-alike businesses found along all of its exit ramps. In the original story, our hopeless anti-hero Humbert Humbert is more of a caricature than a real person, in love with our underage anti-villain more for the idea of what she represents, not for her herself; only half the book, in fact, is dedicated to their meeting, relationship and decision to flee together, while the other half is a bleak tale of life on the road, Humbert's day becoming as dully ritualized as he was trying to escape in the first place, punctuated with semi-imaginary posses that may or may not exist. Surprisingly subversive still, even in our modern age, this one gets a big recommendation from me.
Out of 10: 9.4