This plugin lets you have your own "sig" image that says what your currently listening to in Winamp. No server required. Its as simple as one, two, three. One, sign up on SIGamp.com. Two, Install and configure plugin. Three, post your image anywhere you want. This plugin works with Winamp 2.9 and Winamp 5. It will not work with Winamp 3. Need help? Get it at SIGamp.com/support/.
Well it does what it says and it is free (it appears that if you want to alter the image/style used then you need to become a subscribed member of the service, wasn't too clear i found).
Was installed quickly and the installer provides good information on what's needed to setup the plugin so you can start using it asap.