iTunes lacks alarm clock functionality and I wanted to wake up to a random song so I created a small script file to launch iTunes and play from my last view (mostly shuffle here) and set it up as a Scheduled Task in Windows (via Control Panel). You don’t need to keep iTunes open. A new process will launch if necessary.

You can download it here or create your own with the following code:

var iTunes = WScript.CreateObject("iTunes.Application");
iTunes.Play();

Very simple stuff.

Enjoy!