I just came back from a long stratch of work but I think I'm almost ready to leave again. I love the road.
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Who would I pick? Well to be nostalgic, and if I could go back in time because it couldn't happen now, my ex. We went hitchhiking together and had all kinds of positive, negative, and just plain weird adventures.
I'd probably also take Hermann Hesse on a road trip. Or maybe WB Yeats.
And last, but not least, Janis Joplin for the sheer chaotic factor. I'd not let her drive though. There's something about Jack Daniels and heroin which would probably make me reluctant to haver her behind the wheel.