Can headphones ever be as good as high end stereo?

I've had good experience with stax! The biggest difference is imaging inside of your head as opposed to in front of you...the clarity is really out of this world with stax!

I could probably live with the TOTL Stax and call it a day. Even my older lowly smaller STAX Electret design phones are hard to beat, save perhaps in bass extension.

Probably TOTL Sennheiser as well. Maybe others....but not quite as sure. SO many good ones for even just a few hundred $$$s. Can't beat the sound/$$$ value of phones.

Can be, just depends on whether you enjoy sitting listening to headphones or not.

Another good thing about phones is they are likely to sound much like they did in the store when you get them home, with no room acoustics in the equation. That's assuming similar quality headphone amplification in both cases, to the extent needed.

The sound quality of "Audiophile" type phones like those in TAS review Al cited above will tend to be more dependent on amp than say portable phones designed to require less robust mobile amplification.

Plus the cost threshold of top notch headphone amplification for most any phones also tends to be much lower than similar quality speaker amplification due to teh much smaller scale involved.

Its not hard to imagine it a much easier task to drive very small transducers (ie headphones) located up against or even in your ears optimally than it is much larger ones (speakers) at a distance.

ALso full range type drivers are common in phones and no electronic crossover which gives phones a clear advantage in general in terms of phase coherency.

For me, it's not either/or but both/and.

I enjoy listening to my Spendor speakers, and I also enjoy music through my Sennheiser HD800 headphones.

The HD800s were game-changers for me. Like you, I had mainly owned modest headphones before, some basic Grados, and a more expensive pair of AKG 702 (the 65th Anniversary edition). The AKGs made me realize that headphones can be better than I had thought. And now that I have the HD800s, I thoroughly enjoy listening through headphones.

The HD800s have an actual sense of soundstage, unlike headphones that put everything between your ears. They are comfortable, at least on my head. And they sound superb driven by OTL tubes amps, including a modest little Bottlehead Crack and a Woo WA2.

I mainly listen to classical and jazz, and I do like to turn it up when the music demands. The HD800s remain clean at high volumes. (Not ear-damaging levels, of course.) And I don't find them to be bright, at least not when driven by the tube amps I use.

One caveat -- I don't do vinyl. So, I can't say whether record surface noise or turntable mechanical noise would be exacerbated through headphones.

I haven't tried Stax electrostatics--and am in no rush to do so, given how much I like the HD800s.

I might sound like a salesman for Sennheiser but I have no affiliation -- just an audiophile and music lover happy with a purchase.