Ok, I'll stick my neck out and see if I get it chopped. I also smoke my pipe and listend to my ipod classic. When you mention "Bose" it's like poking me with a sharp stick. I'm not only a 40+ year pipe smoker, I've also been an audiophile for that long. I think Bose is the biggest con ever pulled on music lovers. It's not that their stuff is actually "bad", it's that it's highly overrated. You can buy something just as good or better for half the price. If you want to block out external sounds you don't need "noise cancelling", with it's extra, distorting circutry, you just need good closed earphones. I would suggest Shure SRH840 phones. Very good sound, super at sealing out other sounds and a bargain price.
I have 4 headphones and I listed to my Ipod with a Ray Samuels Audio portable amp and cable and all my music in the ipod is recorded lossless.
If you want to learn about "good" portable audio so you can really hear your music while puffing away, you might want to vist this site. http://www.head-fi.org/
I know this is all getting a little off the subject of pipes... but hey, I didn't start the thread.
Happy smokeing and listening to all...