I don't think it matters which ones I choose, as a sixth item would be added to the playlist: My gibberish ramblings and musings at the sheer torment of being limited to five songs :P

But nevertheless:

Final Fantasy VII - Still More Fighting
Iron Maiden - 2 Minutes To Midnight
Avenged Sevenfold - And All Things Will End
Guilty Gear - (I'd be dead sneaky and try and throw a crude medley together using Sound Recorder or something... no? "Suck A Sage" then.)
Congress Woman Malinda Jackson Parker - Cousin Mosquito #1 (Maybe)
Me - Unintelligible moaning and gibberish