Beyerdynamic DT770 (Some version that would run well with slightly lower power not needing a headphone amp), Onboard SB live 24bit >_<. WMP or Winamp :P
Senn HD280 Pro's. don't listen on the go but if i do i use the same headphones on a 60GB iPod. Audigy 2 ZS probably be an X-Fi Soon enough. and Klipsch 2.1 Speakers. Klipsch > Logitech.
Usually my Sony 300W mp3 stereo at home but I have Allesando MS1s as well for when I need to hear a little more range :)
On the go I use my Ipod shuffle with the stock whites. They have developed a rattle from my Hip-Hop music so Im buying Senn MX-500s :D Now I wont look like an Ipod wierdo.
iPod + Sure E2C Canalphones iTunes + X-mystique 7.1 Dolby Digital with Altec Lansing AC890s or something.. soon to be a set of Logitech 5500s I think :)