Honestly it's really all subjective. I've heard from a lot of different people that after you accumulate a large music collection iTunes starts to lag really badly, however the iPod is the most popular mp3 player on the market and it works best with iTunes so it does have that advantage. I've been using winamp for the past three years now and it's so far been my favourite. You can close certain parts of it and it's not as flashy as some of the other media players. I tried Media Monkey for a while and it seemed pretty neat, but I couldn't install the Last.fm scrobbler with it even after looking up ways to get around it. Windows Media Player is fairly simple to use, but does tend to lag a bit after you get a large music collection. All in all it really comes down to personal preference, I think winamp is the best, however I've heard a large number of people disagree with me.
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