I'm not an audiophile but I'm very sensitive to comfort level of something. If it even slightly bothers me, I notice it immediately. So here's my opinion on the top most comfortable and popular headphones. Personally I've tried on Audio-Technica AD700, Sennheiser HD598, Beyerdynamics DT990 Premium 250 ohm. I've also ordered Sony MDR MA900 and it's on the way so I will comment on the comfort level when it arrives. AD700 - Pretty heavy. No horizontal swivel. Uncomfortable headband. No earcup height adjustment. Digs into area under the ears. Velvet texture itchy, not the most soft cushion. Once you adjust the metal bands they are loose fit. If I shake my head or bend down, headphone falls off. Really really wide soundstage I think. I feel the wide space around me when I play Red Orchestra 2. Not a lot of bass. HD598 - Very light. Horizontal Swivel, solid earcup height adjustment with clicking notches, Good headband comfort, No digging anywhere around ears, Ridiculous soft cushion, feels like cotton balls, Velour good texture. Headband clamp really tight at first but really not uncomfortable at all. A bit tighter above the ear but I like that more than under the ears like DT990 does. Decent amount of bass, much more than AD700. DT990 - Really heavy. Really really comfortable headband cushion. Tight clamp at first. After putting books between the cups and stretching them out, it's somewhat comfortable but it's loose just like AD700. It moves and falls if I shake my head or bend over. Earcup texture is extremely soft and amazing velour. It's just dreamy. But the sponge inside is stiff like cold memory foam. No matter how stretched the headband is, the cups still dig under my ears and I don't like that. Lazy earcup height adjustment, not smooth and no 'clicks'. But I can see how some people might like the metal construction over plastic like HD598. I just found HD598 much more satisfying. Very nice bass much more than HD598 and AD700. MDR MA900 - I don't have it yet but I will get it this week. What I expect: Very lightweight, lighter than HD598. Same sound quality as HD598. Somewhat comfortable headband. Not the best earcup height adjustment. (no notches/clicks, flimsy design) What I'm wondering about the headphones: Will earcups dig under my ears or make my jaw joint uncomfortable? How comfortable will earcup cushions be? Will the cloth texture be acceptable? I will edit my post once I get my hands on the MA900.