Winamp may be an unfair comparison. I'm not overly familiar with that period's iTunes, but I remember when I bought my first iPod, a 4th gen click wheel (don't

Winamp may be an unfair comparison. I'm not overly familiar with that period's iTunes, but I remember when I bought my first iPod, a 4th gen click wheel (don't remember the year, but it was already an "older model" at the time) I was using Amarok on Linux on an AMD Thunderbird with 256 MB of RAM. That thing would fly. And it did more than Winamp: it had an actual DB-backed music library, iPod interface, etc. Yet, a few years later, when I got a MacBook Pro with a dual-core CPU and 16 times the RAM, iTunes would still be painfully slow. And I don't remember it doing much more than Amarok. As a matter of fact, it was inferior on pretty much every metric I could think of.