The most comfortable phones that I have are: Sony R-10, Sony CD3000, Stax Omega II, Beyerdynamics DT-880, DT-770 Pro, DT-990 Pro, Sennheiser HD-600, Audio Technica W-100. I totally agree that the AKG K-1000s put a lot of pressure on your temple, as do most Grado headphones. Other than the Sony R-10's and Stax Omega II's, all of the other cans mentioned above are reasonably priced (from under $200 to $400 range) and widely available.
Headphone I can stand for more than 1 hour
Every headphone I have ever had starts to drive me crazy after 1 hour. I started with the Sennheiser HD 414. Warm foam cushions and push too much on my ears. Tried the AKG K-1000. Too heavy and push on the side of my head. Grado SR 325 - too warm. Why can't anyone make a headphone that sounds good and one I can use for a couple of hours? Have you found a comfortable one yet?