Chad,
The only thing I can think of would be this post:
http://www.clearcanvas.ca/dnn/Commu...fault.aspx
This was related to Windows Server 2008 R2 installs, where static content was not being served. I think the characteristics of the issue is slightly different, however, than what you're seeing. Ie, some content was displayed, but images were not displayed.
Otherwise, I'm not quite sure what the issue could be.
Steve