This script reads information about my most recently played song from iTunes, draws it on an image, and uploads it so it can be used online. The script is written in AppleScript and uses iMagine Photo, a lightweight and scriptable image editor, to draw the avatar. The script runs invisibly, redrawing and reuploading the avatar whenever a new song is played.
Update: I have moved away from iTunes and OS X so this image no longer updates. The script ran trouble free for seven years. RIP
If you’re interested in using the script yourself configuration instructions are included in the download.