After hunting around for the last few weeks for a free, zippy and reliable iPod music ripper for Mac, my search culminated here. Even though I ended up paying for iRip, I believe it was worth it after my initial experiences with the software. It lets you interface with iPod, iPhone or any other music device and transfer music with ease.
The LittleAppFactory also has other awesome software like the Evom that lets convert movies and youtube videos to ipod compatible formats, RipIt that lets you rip movies from DVDs etc. I have tried both of these and they are super-efficient and easy to use just like iRip.
Great job, LittleAppFactory!
P.S these are software for Mac.