Reading through this OLD thread, I was surprised that no one mentioned the Beatles "Rain" for quite a while (although it finally rated a mention). That song is special for me because itwas on the set list for my first and only-ever paying job as an electric bass player. (It has a very simple, but very interesting, Paul McCartney bass part.) And I thought of one more pertinent song, completely omitted so far (I think): "Box of Rain" by Phil Lesh of the Grateful Dead. It's a very complicated piece and devilisihly hard to sing; I doubt that it was ever performed live nearly as nicely as it sounds in the near-perfect studio version.
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