There have been some nice new "advertiser sponsored" free music sites to pop up over the last few years.  One of the most promising is Spiral Frog (http://www.spiralfrog.com).  The downside to pretty much all of them has been that songs downloaded from these sites are digital rights managed (DRM) which is used to ensure that only licensed users can listed to the files.  Basically once you download one of these songs, you can't email it to your friend and let them listen -- they will get a license error.

This technology for digital rights management is essential so that the already struggling music industry doesn't lose what little money it is making.  It used to make a killing on CD sales, but not anymore thanks to illegal music distribution online.

So, the upside to DRM is that you can't give illegal copies to your friends.  The downside is that if you use a service like Spiral Frog (which uses Microsoft Windows Media Player for DRM and playback), then you cannot put those files on your iPod or iPhone.  Hey, the technology isn't perfect... YET.

There is a solution! (you knew i was going there, right ?)  This requires you to be a morally responsible person however, and any "gray" areas on this are up to you to decide on.  I am not, in any way, endorsing this information, I am only providing it as a public service.

There is a nifty open source product called AnalogWhole (http://analogwhole.com) which removes DRM from your windows media audio files (it doesn't support video at this time).  Once you configure AmalogWhole, it will watch your incoming folder for new music files, and automatically convert them to plain MP3 files _AND_ add them to your iTunes music library (f you want).

AmalogWhole isn't a perfect program yet -- it actually plays back the original, and does a digital recording to a new audio file, so the speed is 1-to-1, your computer has to play back each file.  It is a little quirky in that your volume level of your speakers (from within windows) affects the recording level, so it takes a little experimentationi.  After all the effort however, what you end up with is a clean MP3, automatically added to your iTunes library, ready to sync to your iPod and it sounds pretty good.

Once you have a process down like this, it allows you to take advantage of advertiser-sponsored free music sites like SpiralFrog, and then also add that music to your portable audio player, just as we _should_ be able to.  All it requires is discipline to not distribute those unprotected audio files, and thus making the music industry we all love collapse on itself.  You can do that right ?

Ciao, and stay LEGAL !