The best album to listen to in the rain is Elliott Smith’s second posthumous album: a two-disc compilation of B-sides and early versions written and recorded from 1994-1998. Titled New Moon, this album is perfectly melancholy for the rainy monsoons. Yet, it's blissfully reminiscent of a time when Smith had his shit together, and before his untimely death in 2003, it reminds us that this may be the last of his brilliant work we might ever hear.
There really isn’t much more to say. It deserves a listen.