Here's an Applescript to make skipping to random tracks in iTunes a bit more like scanning through FM radio stations: it will select a random track and start playing at a random point. Save it in
~/Libray/iTunes/Scripts and assign it a key in Keyboard Shortcuts.
on run tell application "iTunes" set t to some track of playlist "Library" play t set player position to random number from 0 to duration of t as integer end tell end run
load in Script Editor