The second option I tried, and the one which worked for me, was using the Last.fm client. Before I did this, I bought my latest shiny new toy – the 15.4″ Santa Rosa MacBook Pro – and so this section is using the Mac OS X version of the Last.fm client. Having installed the program I noticed that there was an iPod section in the Settings menu. Once I set up my (Dad’s) 5.5G 30GB iPod to sync with the MacBook Pro’s iTunes, to a playlist called ‘iPod Music’, I tried to get it to scrobble. According to the Last.fm website, the iPod must not be manually managed for this to work, and this was how I found it to be as well.
In my experience, iTunes on the Mac must be closed before the iPod is connected. Whenever I have had iTunes open the ‘scrobble your iPod’ window hasn’t appeared. Remember that this is still an experimental feature at the time of writing, and so this may change in the future. If you do have iTunes closed when you connect the iPod, then it will automatically open when the iPod is connected, and the Last.fm window will also open (although sometimes it opens behind the iTunes window, so make sure to look for it). Also note that the scrobbling process is not totally automatic. The scrobble window presents you with a list of your plays, with checkboxes next to each so that you can choose to not scrobble some tracks, because for example, you have scrobbled another play later than that one, and so scrobbling it would trigger Last.fm’s spam protection. When you are happy, simply click ‘Scrobble Selected’, and these plays automagically appear on your Last.fm account. Simple as that.
I have not yet been able to try this with Windows, because the only Windows-managed iPod we now have here is my brother’s 2G Nano, and this is manually managed. I will at some point sync one of the iPods to Vista and see if those plays will scrobble too, although Adam Zethraeus has told me that he can’t get this working on Windows with his 5G.
Good Luck and Good Scrobbling…