What was the first pair of headphones that made you say HOLY CRAP?

Welcome to the forum. The Sundaras should be a good upgrade that shares the same sound signature. If you found the SHP9500s too bright, I’d suggest considering the Sennheiser HD6XX. I personally opted for the HD6XX over the Sundara.

Another possible option that I haven’t heard yet is the ibasso SR2. See some impressions here, mostly positive: iBasso SR2 - Official Thread.

Note that these upgrades will likely call for a slight upgrade in amplification to reveal themselves to something like the Schiit Magni 3+ or Asgard 3 (and a DAC such as the Modi 3+ or Modius).

Good luck.

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