Not a single Cherokee server :(: http://cherokee-project.org
I would argue that the GUI model of configuring complex server-type services is generally wrong. At most, GUIs are good for tweaking configurations, not for setting up a baseline config to begin with.
In the end just firing up Nginx was quicker to configure, easier to understand and most of all easier to debug.
Still it a webserver I like to pull out and play with every now and then, even if I end up just using Nginx.