Interestingly, when it first came on the scene as SoundJam, and in its earlier incarnations at Apple after it was bought, iTunes was by far the best music playe

Interestingly, when it first came on the scene as SoundJam, and in its earlier incarnations at Apple after it was bought, iTunes was by far the best music player out there[1]. The overwhelming favorite MP3 player on Windows at the time was WinAmp, whose UI was a ghastly collection of inscrutable, tiny fonted palettes. Compared to that, having your entire collection of music in a smart, scriptable database with a slick interface was a dream. Performance problems on Windows and tacking on one new non-music playing feature after another seems to have doomed the experience and reputation. [1] Well, Audion was pretty dope too: http://www.panic.com/extras/audionstory/ http://www.panic.com/extras/audionstory/