Headphones vs speakers….

fsonicsmith1 - I like all your analogies but I’m glad you stopped before you went too far. Red Burgundy is made from Pinto Noir grapes, not red Zinfandel ( original indigenous North American grape) & the two  are her different. Both can be excellent but it’s like comparing a tube amp w/ a class D solid state. Maybe a delicious Oregonian Pinot would have been more appropriate?

my ears hurt and I tend to cause a lot of accidents after 30 minutes when I wear headphones. Am I doing it wrong?

Stereo is engineered so that the right ear hears some of the left speaker and and vice versa. 

Not necessarily true. In fact, most times not true. I would even go so far as to say that "stereo is engineered" is an oxymoron. I won't elaborate. Talk to someone who does studio engineering or simply read about studio engineering. 

Red Burgundy is made from Pinto Noir grapes, not red Zinfandel ( original indigenous North American grape) & the two  are her different. Both can be excellent but it’s like comparing a tube amp w/ a class D solid state. Maybe a delicious Oregonian Pinot would have been more appropriate?

I am quite aware. My analogy to two completely different wines that are not only from different grape varieties but from different countries with completely different character was on purpose. But now we are getting both silly and pompous, aren't we? :-)

I'm a speaker listener as I don't like being held captive by headphone wires and the weight of something hanging off my head and making my ears sweaty. I do use wireless RF headphones open back headphones for late night cinema but that's the extent my experience.

If I were to make the choice of going down the rabbit hole of luxury headphones and premium headphone amps, maybe I'd have a different opinion.

Thanks guys, wow, a lot to read here!

I thought I was done with my quest for great headphone and headphone amp combo but….

I should have mentioned my Benchmark amp and preamp will be used in a small room as I’m now in an apartment. I used to own big Magnapan speakers with great amps and I’ll probably never enjoy music like that again - I like my music loud but I can’t do that in this apartment. I’m out on the town a lot so I use portable headphone amps, right now the Ifi Gryphon. I’m happy but always wondering if there is better in a truly portable headphone amp.

my room is maybe 14 feet long by maybe 12 feet wide so I guess I’ll be giving up good soundstaging which I love. Using Totem 1 bookshelf speakers and will hook up a Velodyne sub with these. However today I swapped the Totems out for a Pair of Paradigm S2 v2 - horrible! My room isn’t yet treated (will be in two more weeks) but the Paradigms were just muddy as hell compared to the Totems and I’m wondering if this was due to the bigger cones on the paradigms coupled with an untreated room.

right now I’m just dabbling with what I have laying around (Naim Nait 5i ) until my Benchmark system is complete with the DAC 3. However, I doubt that will have any effect on the Paradigms sounding better, but who knows how much of this is due to a very untreated room.