Have to admit, I'd have a hard time choosing 5 specific books. That's kinda the point of my kindle, so I always have something to read, even when I'm in a fickle mood.
I'd probably have to narrow it down to a few series, and then I'd pick a book from those series, but not going to worry about that specificity here:
Patrick O'brian's Aubrey/Maturin series
Robert Jordan's Wheel of time series
Anne McCaffrey's Pern series
George Martin's A song of ice and fire
Not sure what series the 5th book would come from, maybe Jim Butcher's Dresden Files (or possibly, Nathan Lowell's Solar Clipper series).
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