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XP and WMP might pre-date the iPod but they were useless in terms of media management and music syncing. For one, WMP default to the .wma format for audio which

XP and WMP might pre-date the iPod but they were useless in terms of media management and music syncing. For one, WMP default to the .wma format for audio which didn't work on any portable player at the time. You could switch it to use MP3's but you had to install an MP3 codec in order to get that to work and most users had no inclination to do anything of the sort. I think the OP's point was that, while you could do this stuff on Windows, it wasn't nearly as functional, seamless, or simple as it was with an iPod and iTunes or even MusicMatch (which really, really sucked, at the time).

Terretta 9y ago
My recollection was Creative Nomad played .wma, which at the time blew away .mp3 quality. And the Creative Nomad ZEN Xtra with 60GB was phenomenal for a reasonably sized library. For software, I recall two options: MediaMonkey Gold, a media player that synced with ZEN players and could automatically convert media formats. Notmad Explorer, a software suite from Red Chair Software that allowed for file and playlist management for the ZEN players.