Marco Arment:

iTunes is designed by the Junk Drawer Method: when enough cruft has built up that somebody tells the team to redesign it, while also adding and heavily promoting these great new features in the UI that are really important to the company’s other interests and are absolutely non-negotiable, the only thing they can really do is hide all of the old complexity in new places.

iTunes is in desperate need of a complete rewrite. Apple’s done it with nearly every other application they ship and I don’t understand why they haven’t done so with iTunes — likely the most important application Apple develops.