FWIW, I just bought the 160GB Ipod classic a month or so ago. This is my first Ipod and I couldn't be happier with this product. I'm using the $100 Bose in-ear headphones and I think the combination sounds great. I'd heard that they've improved the sound quality on the later generation ipods, so I can't comment on the sould quality of the older ipod generations, but I really don't have anything negative to say about the sound quality that I'm getting out of this unit. At 160gb, I'm in the process of loading so much music that I can take with me, it's like have my entire music collection go with me whereever I go, and that's frankly so cool that even if there was a marginal bitch about sound quality (which I have none) I'd still be loving this thing to death. Then to top it off, I haven't found one thing that I can say bad about the itunes software which is really amazingly bug free. I'm especially senstive to this after using various Sony software that have been packaged with their hardware products. USually what Sony puts out is so buggy that it's more risk using it than not. This is just not the case with the itunes. So, I honestly would rate my whole ipod experience pretty darn close to 10 stars outta 10.