The HE-4XX reminds me of my departed HE-500 and HE-6; it's slightly more comfortable due to the improved headband, but not by much. It still feels heavy and the earcup height adjustments are fiddly and can be annoying. When I switch between the HE-4XX and HE-400i I prefer the HE-4XX for its more balanced sound, but the comfort factor detracts from the overall experience for me. Then I put on my HE-400S - this headphone features the same improved headband design as the HE-400i but IMO the sound is more balanced and natural than the HE-400i (though lacking in the details the HE-400i provides). If one finds the HE-4XX to be comfortable then it is one of the best values in headphones. I find it to nestle in a spot between the sound signatures of the HE-400S and HE-400i, which many may find agreeable and preferable over the newer HE-400i/S cans. I slightly prefer the sound of the HE-400S to the HE-4XX but I also prefer the sound of the HE-4XX to the HE-400i. I'm glad I tried this headphone and applaud Massdrop for their efforts in improving the old HE-4/5xx design and achieving such a low price for a great sound.