I've just written a contextual menu plugin for iTunes that adds a Play Similar Artist Radio in Last.fm item to the menu when you right-click on any song -- it even works when you right-click on albums in Cover Flow. First it pauses iTunes (if you happen to already be listening to something), and then it launches the Last.fm client and automatically tunes into the similar artist station for the artist of the song you right clicked on. This is an excellent way of discovering new artists similar to ones already in your iTunes library.
The plugin should work with most versions of iTunes, and can be downloaded here.
[robg adds: I tried this one, and it worked as described. You'll need the Last.fm client, obviously. The plug-in even includes Growl support for notification of station changes.]
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