Please help my find a pair of headphones that won't hurt my head or ears.

I won't use anything but my Sennheiser HD600's, by far the most comfortable circumaural cans I've ever used. The cans themselves are very very large, the pads, cord/etc are replaceable. They are, however, expensive. I've had mine for about 6 years now, replaced everything on them, dropped them, kicked them, sat on them. They are awesome.

Seconding meowzilla's Koss recommendation. I have a slightly older version than the model meowzilla linked to, and I find them really comfortable and the sound is really good (surprisingly good, given the cost). I have some other 'phones (Sennheiser and AKG) that were a lot more expensive, but I rarely use them unless I'm actively listening to music as opposed to listening while working or walking around.

nthing the SHure in-ear headphones. I count my e3cs as one of my most worthwhile gadget purchases, right up there with 24" monitors. Unfortunately, the cords wore out on mine after 3 years, and I would guess that will be typical after daily use, so be aware of that. I'm trying to decide whether to replace them with se420s or se530s.

Thanks for the help, all. You've given me a good place to start. Once I've settled on a pair, I'll let you know which ones I chose.

If circumaural ones give you headaches, is it because of physical stress or pain (like with the supraural ones)? If not, it might be a psychosomatic effect, like a lack of environmental acoustic information distorting your balance. In that case, it's worth checking out open-design circumaural phones, as opposed to closed ones.

I really like my http://www.skullcandy.com/shop/gi-p-6.html?zenid=60ebff2db61e55a16e86378ad341d024 I find them comfortable and the sound quality is good. I also don't like earbud type headphones, but I do not wear mine for 8 hours a day so I can't attest to how they will hold up comfortwise for that amount of time.

The Koss headphones mentioned above, while sounding awesome, are very leaky. I can't use them in the office since everyone in the office would be distracted by my tunes. I have a pair of the Shure E2cs, and I can't wear them for very long without a lot of irritation, even with the smallest and softest tips. I think my ear canals are just too small. I have a pair of MDR-E888LPs, which are earbuds that I wear for 8 hours a day. They don't hurt my outer ears like every other earbud I've used, and the sound isn't fatiguing. They're very highly regarded in the audiophile community.

If you want large, over-the-ear headphones, Sony's MDR-V6 (and its twin, the MDR-7506, but not its near-namesake, the MDR-600) has a good reputation for comfort and sound quality. It's pretty widespread in studios, too (so are Sennhisers), which is probably a good sign. If you haven't tried the audiophile and near-audiophile (Shure, Etymotic, Ultimate Ears) in-ear monitors, and sound quality is what's holding you back, you oughta give 'em another try. If it's comfort, though, well, I can't blame you. I don't think in-ear monitors are very comfortable either.

Seconding the Shure E2c's. Durable, forget-they're-there comfortable, and very good sounding. Excellent customer service too.