I've seen a couple of post of people referring to the 5th gen as 5th gen classic. There's no such thing as a 5th generation classic. 4/5/5.5 gen ipods are called ipod video. The classic line starts with the 6th generation. Now I've own an ipod video, iphone 3g, iphone 4, and 6th gen classic. I haven't listened to the current ipod classic and I hope it's a big improvement from the 6th gen because the 6th gen is the worst sounding ipod I've ever listened to. Even the iphone 3g sounds significantly better. The sound was dull and lifeless(to my ears). Of the ones I've owned, the iphone 4 has the best headphone out, and the ipod video has the best line out. Well, the best sounding line out. There is a little hiss, and the line out from the iphone 4 is dead quiet. But sound is so subjective, and like UncleErik said, non of them will compete with a good cd player or dac. Not even and imod. A modded ipod(and yes I have one) is better than a stock ipod video, but it doesn't transform it into an audiophile source. It comes close some budget cd/dacs, but that's about it. But take them for what they are. A very convenient, portable source where you can take your music with you and enjoy anywhere. And for that purpose, they are all great.
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