Simple is Easy.

Nightingale is a free, open-source music management program that is based on the  Songbird media player source code. It has a slick and user-friendly interface that can be customized with 'feathers', Nightingale's answer to skins.

iTunes is a free application for Mac and PC. It plays all your digital music and video. It syncs content to your iPod, iPhone, and Apple TV. And it's an entertainment superstore that stays open 24/7.