Search around for references to alternatedoctroot. It's in GFv2, and it works really well.
In essence, you put an entry in your sun-web.xml (among other places).
<property name="alternatedocroot_1" value="from=/images/* dir=/usr/gifs"/>
So, this would map:
http://yourhost.com/images/pic.gif
to
/usr/gifs/images/pic.gif
The key is that you while you specify a path to mount the doc root on (in this case /images), the value you give it is actually the root of the request, so you need to create a /images directory underneath it.
So, as I said, pic.gif maps to:
/usr/gifs/images/pic.gif
vs
/usr/gifs/pic.gif
The point is subtle and it's easy to get confused when your content doesn't work.
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