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I'm working through a bunch of counter-culture classics this summer. I've just finished The Dharma Bums and Inherent Vice by Pynchon. Now, I'm working on Naked Lunch, Catch-22 and A Clockwork Orange, which all take very different mindsets. I think Naked Lunch would make a lot more sense high on opium, but Catch-22 has been a mix of hilarious and sympathetic for me. I'd highly recommend The Dharma Bums and Inherent Vice as great intros to their respective authors, without the difficulty of say Desolation Angels or Gravity's Rainbow.