Videora iPod classic Converter is a free iPod classic video converter that converts video files, YouTube videos, movies and DVD’s so you can play them on your iPod classic.
The software, developed by the creators of Videora, can convert all types of video files (avi, divx, xvid, flv, x264, vob, mpeg, DVD’s, YouTube, etc.) into the proper video formats (MPEG-4, H.264) that play on the iPod classic. It is available for Windows and Mac.
Download Videora iPod classic Converter
Book2Pod is a utility to format large text documents so they can be read on an iPod using the built in Note Reader software. It supports documents larger than the 4KB per note limit of Note Reader, and makes the 1000 note limit easier to work with.

It also lets you organise your collection of electronic books and supports Services.
Book2Pod 1.2.2 requires Mac OS X 10.3 and an iPod with firmware version 2.0 or higher (Dock connector or iPod Mini). It is freeware.
Download Book2Pod for Mac
iPodBackup is a shell script-turned-application (via Platypus) that backs up your home folder to your iPod using the open source backup utility rsync. Combine it with Do Something When to have fully automated incremental backups to your iPod, for free!

You can customize a list of items to be excluded by simply dragging-and-dropping them onto the app. By default, the Music folder, as well as certain cache folders are skipped, in order to prevent duplicating your music and because caches are a kind of stupid thing to backup.
A note for first-time users: The first backup can take quite a while, especially if you use an encrypted disk image! Subsequent backups will be much faster, as only files that have changed will be copied over.
* iPodBackup will backup your home folder, wherever it may be, either to Users/username, as a folder, or to Users/username.sparseimage, as a disk image, on your iPod. The disk image may be encrypted or unencrypted.
* iPodBackup is untested on OS X 10.2 and earlier. Version 1.0.x should work, but 1.1+ requires OS X 10.3 or higher if you want to back up to a disk image. This is due to system-level changes in handling sparse disk images.
* Your iPod should be set to be used as a hard drive. Enable this from within iTunes. This is not technically necessary, but otherwise your iPod may be automatically ejected before you can begin the backup.
* According to user reports, PC-formatted (FAT32) iPods will work given that you backup to a disk image, and your data is less than 4 GB (Apparently FAT32 has a maximum file size of 4 GB). I have not tested this directly, so proceed at your own risk.
* To automate the backup, i.e. have iPodBackup launch automatically upon mounting your iPod, use Peripheral Vision (US$6.95), iPod Launcher (US$4.95), or Do Something When (free).
* iPodBackup is distributed under the GNU General Public License.
Download for Mac