I have to disagree with you a bit. I had a pair of Denons (d2000's) that were nice.
Awesome. Definitely more comfortable than the Grado's but I think you're exagerating the discomfort of the Grado's a bit. At least I dont have the issues you seem to have experienced so quickly, but I've had some discomfort issues. Usually I just switch to Jumbos, turns my Grado's into Denon's
That last part was 1/2 in jest, 1/2 serious. The reason I didnt keep the Denons was the trade off in the sound exceeded the increased comfort. My perception of the d2000 sound sig is, too polite with recessed mids. When I listen to my guitar heroes I'm not looking for polite and I didnt like the mids, but that's probably why I like the Grado's because of the forward mids. Lot's of ways around the comfort issue with Grado's, using jumbo's are one but they dampen the energy a bit and recess the mids. That is they get polite and have recessed mids, just like a Denon. At that point though the Denon probably is a better all around headphone. The Grado though can give me three different sounds, depending on which ear pads I'm using, comfies, bowls, or jumbo's. You can also tape the bowl pads as an additional tweak.
Sound wise I prefer every Grado I've ever heard to the d2000 I had, comfort wise is a different story, but again the Grado sound to my ears is so much better than the Denon sound that the comfort thing is really a non issue with me.
I'm really not. They were literally pushing into the top of my ear; it was just awful. I can honestly say I'd never experienced any sort of headphone fatigue prior to these Grados, neither physical nor aural. But these cans had a signature (it's the highs) that after 5 minutes made me wince. And I kept trying and trying and trying to like them. But when a $200+ headphone literally causes you pain, how do you justify whatever positives remain? I know what you mean about the midrange; the Grados definitely throw it at you and the D2000 is pretty recessed, but it managed to keep me totally happy for metal for quite some time. I'm past the Denons now in any case, using T1s and awaiting LCD-2s. I'm sure the jumbo and comfies are a different story, but I am just bewildered by how people wear the bowls in comfort. My ears aren't big, and I've worn some cans for 14 hours straight. But the SR225i's were like light stabs to the ear, physically and aurally.