iTunes is the best music player/ripper

Version to use:4.7 EDITI'm not sure which version to recommend - new versions offer podcasts but take away from your ability to use the media to the full extent of the fair use provisions. That's lame. Songbird is probably going to be my new favorite, as soon as it's released. Sign up for their mailing list and you can be in on releases, too.

If you use MP3 or AAC or WMA as your main type of music,iTunes is pretty unbeatable. If you want to rip MP3s from CDs, it also does a very good job. You will need a fast machine because iTunes is a resource hog, but the "smart playlist" and "party shuffle" features are pretty unbeatable. It sets the standard that every player is shooting for except for foobar2000(since foobar2000 just wants to be "lightweight").

iTunes includes some privacy and DRM features that I disagree with. But these only apply to AAC/WMA formatted files and I use MP3. Just be sure you understand what you are signing up for before you start using it. I wish I could use OGG Vorbis, but that won't play on my iPod...what's a gadget nerd to do?