Just in case you’re like me and occasionally get on a CLI bender…

Install mpg123 (via Fink or Darwinports).

Let’s say you have an existing iTunes-organized music folder at its usual location. Start by getting a list of all of the .mp3 files in that directory and its subdirectories, and saving the list to a file on your Desktop:

find ~/Music/iTunes -name "*.mp3" > ~/Desktop/allmp3s.txt

Next, we feed mpg123 the full list of mp3s as a playlist to randomize:

cat ~/Desktop/allmp3s.txt | mpg123 --shuffle --list -

And that’s that. If you’d like a playback time indicator, add a --verbose flag to the mpg123 command. Rock on!