I've tried this with my iPod and it works. You just gotta be careful with the text you choose, as it might not have all the characters you want.
Tut by Lethal_B.
ONCE AGAIN, YOU WILL NEED
For this part of the tutorial, you'll need;
<1> A Fifth Gen iPod (iPod Video)
<2> iPodWizard. The latest version is v1.2, and the download can be found through this link -
http://sourceforge.net/project/showfiles.php?group_id=153441
<3> iPod Firmware/Updater. I recommend you guys use version 1.0, as it is the most stable. The download of iPod Updater 2005-11-17 v1.0 can be found here -
http://www.megaupload.com/?d=Y44N4BER
<4> iHack -
http://www.ipodwizard.net/attachment.php?attachmentid=3392&d=1127... NOW TO BEGIN..
<1> Extract and load your iPodWizard Software.
<2> Click
"Open Updater" 
<3> Load the iPod Updater that your just downloaded. I recommend v1.0 (2005-11-17), but it should work with any other Updater.
<4> Under the "Firmware" menu, select your 5g iPod.
Once you have done that, click "Load".
CHANGING THE FONTS
Click on the
Fonts tab
After you have done that, click 'OTF FONTS'
Now, change your index to
4 
Now, click
Make Font. You can choose from any of the fonts in the 'font' menu.
You can experiment here, but from what I have gathered through trial & error, you are best off keeping the writing
Regular, and @ size
18. Once you have finally decided, click
OK.
You will now notice that your chosen font has been incorporated into the index of fonts, like so..
As you may notice, I have chosen
Comic SANS MS, but you can choose any style of font you desire.
Once you are done, you are ready to write them to ye iPod.
Click "Write" which is located at the very top in the center.
Once the confirmation that the changes you implemented were sucessfully written onto the updater, You can exit iPodWizard.
TRANSFER FONTS TO IPOD
All you have left to do, is simply connect your iPod to your PC and use the "Restore" feature on the Updater to rewrite the firmware with the modified version.
However, if you don’t want to "Restore" your iPod (Which deletes all content), You will have to patch the Updater with
iHack
iHack will set the iPod’s firmware version a small amount below its current level before you run the iPod Software Updater, re-enabling the "Update" button. Open iHack (you will find it at C:/Program Files/iHack/ by default), and click the "Patch..." button while your iPod is connected to your PC and the
disk mode feature is enabled. Select your iPod’s drive letter, and iHack will do the rest. Now click the "Update" button, and you will have successfully changed the fonts on your iPod.
Changing the text of your iPod
