One small annoyance I’ve had for some time with iTunes is the fact you can’t keep the video window “always on top” of other windows. This is really annoying if you are trying to work and watch your favorite podcasts or movies.
Currently there is no way to accomplish this with iTunes. However I found a nice small program, for Windows and Apple, that allows you to designate any window you want to always stay on top!
For Windows: PowerMenu
Description: PowerMenu is a small application that adds some extra menu items to the windows control menu: Always On Top, Transparency and Minimize To Tray.
For Apple: Afloat
Description: Afloat is a small Cocoa plug-in that adds “Keep Floating”, “Always on Top” and “Make Transparent” commands to the Window menu of many Mac applications.
Once installed simply right-click your iTunes video window and select “Always on Top” from the menu. Now you can easily enjoy your favorite videos while working away!