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Zune vs. iPod. The iPod wins, hands down.
Not only did the Zune come late to the game, the iPod, made by Apple, had already hit the many millions-sold mark by the time Microsoft had even thought of the Zune. Microsoft, so desperate to compete with arch-nemesis Apple, released the Zune knowing full well that it would barely scrape the marketshare dominance of the world-loving iPod -- a device which revolutionised portable music storage and playback.
The Zune was clunky and lacked the simplicity of the iPod's user interface. It was disproportionately priced for what it offered, and lacked compatibility with existing music software -- namely iTunes.