Most of the discomfort of using Grados can be cured by gripping either end of the headband and easing them apart, which slightly bends the metal into a slightly wider arc. It actually recommends you do that in the instruction that come with them. The earpads aren't great though also, but I've used my SR80s for 3-4 hours in a single session without serious discomfort.
For me they sound enough better than anything else I've heard to more than make up for the comfort issues. After hearing Grados, even top end Senheiser, which I used to think were great, sound muddy. Senheisers are warmer and have a bigger sound and more bass, but they don't pick out as much detail (particularly on voices) and while they are warm, that warmth isn't part of the recording, and again the bass is more than is actually there on the recording. Grados to me sound purer and I love the tight bass.
Connected to the wrong (low quality) device, Grados can sound too bright though.
