Which headphones are comfortable?

Sennheiser and tubes are a good substitute for sleeping pills.

I'm kidding (sort of) I have Senn 600 - and Grado RS-1. I have tube amp with Senns (ASL MGhead) and RA-1 for Grado. I read all the hype about the Senns and they sound great for classical. I like the Grado for rock and jazz (actually Senns are good for jazz also). The Grado's are just more musical and toe tapping. They both have a place in my system depending on the music. I would miss either one if they were gone.

Oh, comfort... ummm the Senns are much more comfortable.

Don't even try the in ear canal phones - I have the Shure E3 and I'd rather stick an icepick in my ear.

Thanks for all the info. The Sennheiser 580s and Grado SR-125s were topping my list and this info reinforces my thoughts.

Grado sr-125s...when of the best hifi purchases I have ever made....great sound,build, and comfort...I listened to these for hours on end with no listening fatigue, discomfort,etc...

Everyone's ears and heads are little different so it difficult to say which headphones are most comfortable. If you like the sound of the Grado's but don't like their earpads (I don't) they make a more comfortable pad that is is usually only offered on the SR-60, but is sold separately. You can cut a small hole in the center of the pad if you think it muddies up the sound.