That’d sum up about 50% of my initial Grado experience … (though one could never really complain about air, or detail).
The other 50% would be me whining about comfort.
Oddly, I LOVE their aesthetic. Even on the bakelite-look-alike SR60 (or whatever alphabetic annotations that model has now).
These 1920s “Grado” headphones made me say HOLY CRAP when they nearly electrocuted me:
My father had an old set laying around and often warned of electrocution risk.
I laughed when someone said on Youtube that Grado has a “1980s retro feel.” AKG’s springy headbands look like the 1980s, Grado has a much more ancient look.
I have four pairs that do this, but none are them are perfect, Some are comfort related complaints, if you could call them that. None are bad fits, but of the four listed below the HiFiMan seem to fit me the best. All make great music. The Senn HD 800 would be the first pair, since its the first of the four I bought, but all four qualify for the Holy Crap Club.
Senn HD 800 - large ear pads get hot. A little too bright with some music
Audeze LCD-X - great cans, but mighty heavy
Hi-FiMan HE-6SE - Love these, but very power hungry headphones
Mr. Speakers Ether 2 - these are my newest set, and they are nice and light. Getting used to the narrow wire headband. They do sound fantastic.
HD800S. I can and have worn them all day very light. When the neighbours get rowdy I switch to my Perfect Seal Deca CIEMs for sound isolation.
The first pair of headphones that made me tear up and shiver were Stax Lambda Pros, they’re what really made me fall in love with headphones and whatnot and really justified all of my purchases in search of them.
They’re old, beat up, and the right driver keeps sliding off of the headband but even after everything else they’re still my favorites.
Yes, I know exactly what you mean. After you are spoiled by electrostatics, you may like what you hear with other headphones, but you keep coming back.
Oh yeah! It hasn’t stopped me from upgrading my other gear and searching for the next best thing but I always end up ecstatically listening back and comparing them to everything, though it has all fallen short thus far. Some day.
Well whatever makes you hear music in a new and unique way, eh?
Campfire Audio Atlas
Oddly the first pair of headphones that made me say “holy crap” out loud were the Pioneer SE-EX9.
Yes yes it’s an interesting name.
I was mostly into audio for the fashion of it because all the “nice” headphones I’d tried up to that point were either remarkably disappointing or horribly underpowered by whatever phones/iPods/DAPs/budget AV receivers I had lying around at the time and I thought that was as close to good as it got without spending condo-levels of cash. I was really into the Persona video game series and the protagonist of P3 used a pair of clip-on supraaurals, so for that reason alone I bought the first pair I could find that had decent impressions over on Head-Fi. Do note this was close to a decade ago.
I vehemently distrust whatever impressions I’d written at the time mostly because I’m now aware of how full of myself I was back then, but I very clearly recall how fond I was of them at the time. I actually unearthed them a little while back but they’ve long since died. Almost tempted to hunt a pair down for nostalgia’s sake, but I would probably do better with a pair of SR60s and modding them.
The next proper “what the fudge” moment was a friend’s Sennheiser HD650 in meet conditions. That’s the one that sparked my current obsession with audio. No mean feat considering this was back in 2015, when I was still actively collecting fountain pens and the like. Now I’m being a bit more careful with purchases, holding off on most hobbies until things are more stable. I’m more or less happy with where my rig is except for a pending amp change, but I might be more interested in a fancy urushi pen first, haha.
I bought a pair of Oppo PM-2 and lost my mind. I still have them and have no plans to ever sell them. As far as IEM’s I bought a pair of Flare Pro’s and am sold on that brand and price point.
Stax 009S driven by KGSSHV Carbon amplifier.
After playing Stax009S and Carbon amp for 6 hours with various music genre, I am convinced that I can live with it until it stop working.
It sounds musical with clarity, nuanced details and decent dynamics.
When I was first getting into audio, I had purchased a pair of HyperX Cloud II’s. It was the first time I’ve ever listened to something with any sort of clarity, not to mention comfort. They don’t call them Clouds for nothing. Though, after I started getting into IEMs, I figured that Cloud II’s don’t work for my tastes any more. I actually find them quite piercing now! Strange how times have changed.
HD800…opened my eyes to how different headphones can be and that they can have unique qualities. The stage and imaging, detail retrieval was “ear” opening 
Among I auditioned
Among I owned (or own atm)
I had several crappy headphones at the beginning - the one I remember best was the Senn HD424 - an improvement over the HD414, but still quite colored. In the 80s I sold Walkmans in L.A. and heard all of those, even upgraded to some better Sony headsets, but none of them lasted long. In the 90s got a Senn HD580, but it sounded too distant, so I replaced it with two: The Senn HD565 and a Grado SR325, both of which sounded good with my wide variety of music. I later tried the HD600 and original HD650 - both good, but not as satisfactory as the 565 and Grado. About this time I got the Bose QC-2, which had a liquid midrange to die for, but too much bass. It fell apart in 3 places, so no loss…
My first big upgrade was the HD800 in 2009, and I heard it on someone’s Lehmann Black Cube amp - astounding resolution! I had a few mid-price headphones after that, like the Grado PS500, AQ NightHawk, Pryma, Focal Elear - all good, but only the PS500 seemed very musical, albeit the bass hump was a no-go. The PS1000e had great clarity and soundstage etc., but was way too colored for the price and heavy weight.
The F.A. Pandora VI was great, very neutral and detailed, but felt like a large bowl of water on my head sloshing around. I got a Beyer DT1350 and added the T51p earpads - extremely great comfort, but meh sound.
So I guess I’d sum it up the wows this way: Senn HD424 for portability, comfort, and OK sound. The Bose QC-2 for a fabulous liquid midrange. The HD565 and SR325 for liveness and all-around pleasure. The HD800 coulda been a winner had I gotten a worthy amp to pair it with, and the PS500 woulda been great had I had the right EQ for that bass hump. My first big wow in years was the recent Grado White headphone, but the PS2000e fixes its flaws pretty well, at a staggering price though!
Somewhat of a combo platter… the first time I plugged my HD600 into my freshly built BH Crack. This was the first dedicated headamp and the first time I truly experienced the importance of system synergy.
My LCD-X’s through the Rupert Neve RNHP. I smiled for days…
I had a couple in my life, but the first one that made me realize how good it could really get is the Stax L700 about 3 years ago. The resolution, detail and speed was just amazing. At that point, I was still deeply into mid-fi, so it was eye-opening for me. At the moment, I need isolation, so IEMs are the way to go (I have the QDC Anole VX), but I can’t wait to buy my first pair of Stax in a couple of months or years !
My first that said “Holy Crap” was Sennheiser 600s. Playing them through Singlepower amp. Now defunct company after several of them started to catch fire.
Those were my early days venturing into headphones.
Next week I will be venturing into electrostatics for the first in earphones. I will be getting my Mrspeakers Voce. I should mention I did ow Martin Logan floor standing speakers. I forgot how much I loved them.
I will report back on my Voce after I listen for awhile.
Like many on this forum I’ve been dabbling in headphones for decades. My first decent pair were the Sennheiser 414 (I still have them somewhere). Along the way there’ve been Grados (225 if i recall correctly, Hifiman 400i, Shure 1540, Focal Clear, but the first “holy crap” pair were the Focal Utopias. Admittedly they’re priced in the stratosphere, but they were the first that had the detail, micro and macro dynamics and “you are there” feeling for me. I made the mistake of putting a pair of Abyss 1266 Phi TC on my head last week and now have a pair on order. That moment was by far the biggest “holy crap” moment for me to date.