Windows only: Pod to PC can grab the music and movies off nearly any Windows-formatted iPod for transferring to your PC, and avoids duplicates while doing so. Install and fire up the software, and if your iPod is connected by a USB transfer cable, Pod to PC should find it and offer up basic stats:
Most notable is that, along with an iTunes-like read on space use, iPod name, and the like, Pod to PC shows how many of the tracks on a device are already loaded into iTunes on your computer. So that "Automatic Transfer" button smooshed into the lower-right corner (Pod to PC has a pretty rough graphical interface, in case you couldn't tell) does exactly that, grabbing uncopied tracks and placing them. Or you can tackle a transfer manually:
Advanced visual cues show you what's in your library already, what's protected or free, and what type of media each file is. Select the files you want, or use the upper-right search bar to narrow-as-you-type search. When you're done selecting, head to the File menu, hit "Initiate transfer," and you'll get a pop-up window giving you the report. Pod to PC can't place the files in iTunes itself, but it does create an "Import File," a simple text document, that iTunes can read to bring in multiple files at once.
The caveats: Pod to PC is not the most stable software we've tested—the inteface is a smooshy thing, and crashes and freeze-ups, especially when attempting to preview a file, aren't exactly rare. But it does work with an iPod touch or iPhone just as well as a first-generation white iPod, and does a nice job of sorting what you do and don't have already. For a full guide to reliable transfer software, check out our guide to copying music from your iPhone or iPod to your computer for free.
Pod to PC is a free download for Windows systems only.