Yes, SharePod (Windows) can do this.
SharePod is easy to use and works!
Heres some of the main features:
- Add & remove music and videos from your iPod
- Add, remove and edit playlists
- Add & remove album art
- View and backup photos
- Copy music, videos and playlists from your iPod to PC
- Import music/videos into your iTunes library, including playlists and
ratings
- Tag editing
- Drag n' drop to and from Explorer
- Simple, clean interface
- Quick to load and use with no unnessary complicated features
- Support for iPhone and iTouch (Thanks to Nikias Bassen, Paul Sladen,
Jonathan Beck, and Christophe Fergeau
for making this possible)
If you're on a Mac I believe you can do this via iTunes.
- Plug your iPod in and launch iTunes
- Select your iPod from the left pane
- along the bottom right edge of iTunes are a bunch of icons. Click on the one that looks like an iPod. It'll bring up this configuration window:
- Click manually manage songs and playlists, then you can go back to the iTunes window and drag them around.
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