WShed - Winamp Scheduler

Wshed is a free program which you can use to schedule the opening of a song/playlist in Winamp at a specific time. It also supports other commands, predefined jingles, cross-fade mixes, random songs and more. You can ban certain songs and also monitor the ones that play at specific time intervals.
WShed also supports opening other files, like pictures, videos at specific times, and can also shutdown the computer.