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Joss Whedon by a landslide. JJ Abrams has never really struck my fancy, whereas I would go out of my way to find some of Whedon's work.

Windows: Foobar2000
Linux: Audacious
Portable: 30GB Creative Zen Xtra

I was using Winamp, but it is resource heavy and seemed to get worse with every new version.

I use Gentoo on most of my machines. After moving away from Windows it is pretty frustrating for me to go back to, although I technically dual-boot a couple of my machines with XP.