Well I was extra bored So I made a python script to help you do this, Make sure you run it in the directory with all your songs.
You can download python here http://www.python.org/download/releases/2.5.4/
Once it has generated the random names, copy the folder of songs to your Ipod. Then you can hit enter and the script will change the songs back to their original state.
[Tested on Ubuntu GNU/Linux, should work with windows tho.]
#Run this in the directory with your songs, and DO NOT CLOSE this until you have recovered the names.
raw_input("Are you sure you want to continue? Make sure not to exit prematurely.")
import os,random
chars = ["a","b","c","d","e","f","g","h","i","j","k","l","m","n","o","p","q","r","s","t","u","v","w","x","y","z"]
old_new = {}
for song in os.listdir('.'):
if song.endswith((".mp3",".wav",".aac")) == True:
new = str(random.randint(0,2000))+random.choice(chars)+song[-4:]
old_new[new] = song
os.rename(song,new)
print "Generated random name"
else:
print "Unrecognized extension"
def recover():
for old_song in os.listdir('.'):
try:
os.rename(old_song,old_new[old_song])
"Song name recovered...."
except KeyError:
pass
raw_input("\nHave you copied the songs to your Ipod?")
raw_input("Hit enter to recover the names")
recover()
It's a bit overkill :P but I love overkill D: