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Mirrors a lot of my impressions. I used to not think that the HE-500's scaled very well, and then I heard them pushed to the max on the Manley Stingray, rivaling the HE-6.
When I had the rare opporunity to do a comparitive article of the flagships (I had the LCD-2, LCD-3, T1, HE-6, HE-500, and the HD800), it was a lot different than I expeted. Like, a lot different. I still need to transfer the ink review over to my website, Audio Excursions, but for starters, it's realy surprising to me just how much more sonics you are able to push out of the HE-500 on a speaker amp. I was listening to everything through the Rein Audio X-DAC and the Cavalli Audio Liquid Fire, and while I hate to admit this, I thought the HD800 destroyed the HE-500 in terms of resolution, soundstage, imaging, and a few other elements, and there were even sometimes when the HE-6 lagged behind the HE-500. Then I put the HE-6 on the Manley Stingray (still being sourced by the X-DAC), and was blown away. Easily on par with HD800 in terms of resolution and detail extraction, and easily besting the HD800 when it came to PRaT. And that bass, oh, the bass was so tight, articulated, and some of the fastest attack and decay times. The HE-500 reached about 70% of the HE-6's performance when on the Burson HA-160DS and about 80% on the Cavalli Audio Liquid Fire. And then came an even bigger surprise when I put the HE-500 on speaker taps. So much more fluid sound, extremely detailed, not quite on par with the HD800 and the HE-6 when it came to resolution and imaging, but very, very close. Slightly less bass, but just as fast as the HE-6, the HE-500 was pushing 90-95% of what the HE-6 is at it's maximum. You really need a high-end speaker amp to drive BOTH the HE-500 and the HE-6 to their maximum. Sure, the HE-500 is more effecient, and is loud with regular headphone amplifiers, but it's like the HE-6's twin when it comes to driving neccessities. HE-500 on the Stingray was about 9.5/10 of the HD800's performance sans detail extraction and the HE-6 matched the HD800. The HD800 should be the exact same price as the HE-6, and the HE-500 maybe $100-$200 less, ideally."
Unless you have a potent speaker amp for the HE-500, get the HD800, it will be better by a noticable difference.