jPod is a free, lightweight Windows application, replacing iTunes
for managing most iPods. It offers standard library functionality (adding, removing, editing) in addition to playlist editing, easy backups, good cover art management, and duplicate checking. The user interface is simple and fast, the executable clocks in at a fraction of a megabyte, and there is no installation necessary. In fact, I encourage you to just put a copy of the ~200KB binary on your iPod for maximal portability.
* Support for iPhone and iPod Touch through 3G/3GS without iTunes (using jPhone)
* Support for iPod Nano 5G
* Support for iPod Shuffle 2G (tested) and iPod Shuffle 3G (untested, no voiceovers)
* Load multiple iPods simultaneously through one instance of jPod
media directly between iPods, retaining all metadata and album art (pic)
* Drag and drop files
& folders from Windows Explorer, etc.
* Manage lost files (pic ... oops, I used to manage this iPod with other software)
* More descriptive feedback during long operations (e.g. when writing database)
* You can now move the application window while it's performing a long task.
* More keyboard
* Fixed some weird behavior with shift key and right-clicking on the list
* jPod is less picky when adding new files, and more descriptive if it fails to add a file.
* Fixed some glitches in parsing metadata from MP3 and AAC files
* Slight redesign of "edit song" interface, album art shows up bigger
* Countless little bug
fixes and code refactoring
* jPod now backs up the database each time it writes it, in case other software wipes out the database. There is a new option to restore from this backup.
* Please read this discussion about compatibility with iTunes.