Sometimes, I plug my laptop into the little amplifier we use for the TV. It's nothing special, although I've got a nice pair of Bose bookshelf speakers connected to it. The sound quality is really great compared to my laptop's built in speakers, or even to the little panel speakers I have in my office. This should not be surprising to anyone. What is a little disappointing, if not quite surprising, is that I get nowhere near that quality out of my iPod headphones. The problem isn't the headphones' drivers, as far as I can tell, but their fit. When I accidentally (or intentionally) press the little earbuds into my ears, tighter and at a weirder angle, I get a really superior sound. It's like several accompanists just joined in.
Since I listen to my music most often on my headphones (and after that on my flat panel speakers), I'd really like to find some headphones that would always sound that good. I'm pretty open to in-the-ear or over-the-head or behind-the-head headphones. I'd even try clenched-between-the-teeth headphones, if they existed and worked well. Some friends have suggested noise cancelling headphones, which seems like a good investment, since I'm on the bus all the time. Mostly I wonder whether the noise cancelling headphones will also have superior audio quality. If they sound just the same, but remove background noise, that's nice, but it's not all that I want.