I have never listened to a quality pair of headphones, only the ones with the various walkmans I have bought. I was listening to my CD walkman for the first time in ages and I thought the sound was alot better then when I am listening at work. The headphones where the ones supplied with my Sony D-EJ725 player which I think are MDR-E805's which are apparently really bad, but sound so much better than the ones I am using at work from my 14 year old tape-walkman. I think the main sound difference is caused by the heads of the in-ear headphones being bigger and plugging my ears better causing better bass response. I still want to replace the work headphones with some more in-ear ones, but not ear-canal ones as I have had problems with my right ear lately with some kind of blockage causing about 80% reduction that I had to take anti-biotics to clear, which started when I tried to remove some wax. I both love and hate bass in music, I never ever turn the bass boost on. If a song has good bass in the original recording then I want that bass to come through. Most people I know seem to turn the bass boost on resulting in to my ears a muddy performance.