We had a CD player for our music-on-hold which kept dying and having to be replaced. So one day I got fed up, and replaced it with an old PC running win98 with Winamp in its startup group, pointing to a playlist file. (So if the power went out, it would start playing music again when the power came back on.) Music on hold has been continuous without fail ever since that day. Comes right back up after a power outage.

The only problem became the selection of songs. The CD player had nothing but classical, and when I tried to put some more modern stuff in there, our boss complained and made me change it back to the same stuff that the CD player had been playing. Sigh.