The old Sennheiser Orpheus (HE-90) is, to me, a terrific sounding phone. I bet the price of the new phones and that set are not too far apart after adjusting for inflation. It was crazy expensive then (something like $18,000), but, people will pay about $35,000 for a good pair and the amp today, so it has more than held its value.
That does not necessarily mean that the new phones will do the same or be held in as high regards. These days, there are plenty of new phones utilizing a greater variety of approaches that were not around in the past (e.g., planar magnetics).
As for the Stax 009 and Woo amp mentioned above, I have not heard that specific combination, but, I have heard Woo amps (to me, they have been consistently crappy) and I have heard the OO9 on the headphone amp I own (Blue Hawaii SE). The 009s sound pretty good, but, in some ways I prefer the 007s (Omega II, Mk. 1) and the Sennheiser HE-60. It is a matter of taste, with no ultimate "best." I could not argue with someone much preferring the sound of phones like the Audeze (I like them too, and they sound completely different from electrostatic phones).