LCD-4’s, on the noisy floor of CanJam SoCal. Also listened to the Abyss 1266 TC’s and the Warwick stuff at that same show, which also both really wowed me.
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Warwick stuff is truly extraordinary especially if you are comparably new to the hobby!
Hifiman Sundara. It was my first open back, first hifi headphone, planar - it blew my mind, amazing resolution and detail, soundstage and energy, it showed me that headphones could create a really immersive experience.
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So, the first pair that made me say holy crap was when I was much younger. Sennheiser 598. First pair of open backs I’d ever seen, and while I still have them and they occupy a sentimental spot in my heart, it’s not that I think they are in any way “holy crap” worthy in an absolute sense. But in the sense that they were a gateway drug of sorts, that was it. Still remember getting them from Amazon and unwrapping and the experience of putting on Joy Division and then The Cure and then Mahler and then Sunday at the Village Vanguard and smiling and smiling. They were a big purchase for me at the time. Now in a world of HD-800s’s, LCD-3’s and ZMF Verite Opens I’ve found new vistas, which I like a lot, thank you very much. But i’ll never forget those 598’s (and the 598c’s that I brought to work with a Schiit Fulla for a long time which were much worse, but were closed and cheap enough that if they got stolen I wasn’t going to sweat it too hard though they never did).
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Probably said something else before but thinking back the Koss ESP-6 in about 1974 really stood out.
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You never forget your first planar experience! Mine was the RAD 0 (so I kind of got ruined from there on out).
RAD 0 + xBass is one of the craziest experiences ever, feeling bass that sounds like it’s coming from your chest is crazy when you’re new ish to the world of full sized headphones.
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RAD-0 wasn’t my first, it was a Modhouse Argon Mk II. Which is a whole lotta fun!
But the RAD-0 was my first “wow, holy shit that’s fantastic” planar!
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I agree, the RAD-0 was my first holy shit planar experience. I’d previously tried a Meze Empyrean (which I liked) and Hifiman HE-6SE V2 “Adorama special” (which I didn’t like) in my system, and then borrowed a RAD-0. I think “Holy shit” were actually the words I used, because it hit every single preference of mine. I immediately reached out to @taronlissimore, who had just received a new shipment of models from Rosson, and the rest is history.
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Sennheiser hd650 and audeze isine20 with lta mz2. This is what got me scurrying down the headphone path. I had it next to my bed before going to sleep when I couldn’t listen to my speakers late at night.
My holy shit moment would not come until I bought a zmf Aeolus. The added weight and bass over the hd650 was what really made me a serious headfile in this hobby.
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The very first headphone that I thoroughly enjoyed and got me into the hobby was Hifiman HE-5. I wish I’d never sold them.
However, the headphone that made me say “holy crap” and made me drop everything I was doing and thinking was Stax SR-404 Anniversary Edition. I am still hunting those.
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Agreed! Mine was the Audeze Sine DX (!). It still is a great little gem and still love to use it.
Before that, the first “wow” headphone and the one that triggered the hobby was the Ultrasone HFI2200. I know, a much-discussed brand, but back in the days, that was ear-opening for me; the S-Logic design did the trick for me.
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I never said that because, well, I never felt like it really! But my current 1MORE bluetooth, Active Noise Canceling headphones have been the ones I’ve loved the most. Good canceling of general white noise, quick charging, nice sound overall with all sources (laptop, smartphone, digital piano). Which is unfortunate in a way because I recently lost the 3.5 mm to USB C cable that came with them - and I am utterly unable to find a replacement that actually works! Note: the USB C is to receive audio into the earbuds as an alternative to bluetooth - which is great for planes and my digital piano.
Early on for me was the Grado GH2’s and Focal Elex’s. Then I was all in with this hobby. 
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Several years ago, my then new Audio-Technica ATH-MSR7b made me melt for the first time. And now I am here. Good sound can be dangerous.
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I’m entering this a few days late. But, Campfire Solaris with Walkman whatever, plus cayin C9. Good lord!!!
Cans: It was a one-tube amp (Aune something). I had loads of fun with it. Bottom line: ZMF Auteur!!
YMMV
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Raal Requisite SR1a with HSB2 Amplification.
A rather lofty standard.
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Indeed, but @tmarshl has a point. Per my audio show trials last year, RAAL was the only $10K+ setup I’d seriously consider. To my ears it’s that different from others in the TOTL class. Now, coming up from below one might be wowed by the HD-600 on first listen…but if coming in from the same price-class…it’s still amazing…
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I like what @generic said. The “WOW” factor depends in part on where you were coming from.
So, my WOW moment was back in 1979 when I got a pair of Yamaha HP-3 headphones for my birthday ( 21 years old, that’s a Wow now coming up on 65. ) I was coming to them from a pair of headphones that came with a Montgomery Ward turntable + amp combo. Really cheap stuff, so the Yamahas were way away better. I enjoyed them for years then stored them away. A couple of years ago I got them out and found that they needed new pads, which I found some that would work. They still sound pretty darn good, especially for 40+ years old.
Mark Gosdin
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I think Wow is the wrong word.
Coming from 2 Channel, I really just considered headphones to be a compromise.
My first acceptance that headphones could be more than that was probably a Focal Elex, driven by a Monoprice Liquid Platinum from a Schiit Gungnir. It did enough to act as a gateway drug to headphones for me.
Actual real Wow! moments on the headphone front, MySphere 3.1 off the DNA Stratus (Nearfield like presentation), D8000Pro (ability to reproduce nuanced Bass), Susvara of the WA33 (low volume dynamics), Utopia off the DNA Stratus (Dynamics and Stage), RAAL CA-1A (speed), 1266 Phi TC off the Cavalli Liquid Gold (visceral presentation).
At least one of those headphones I consider to be too flawed to really enjoy, but Wow implies to me an initial impression.
There is a lot of personal experience in what impresses you, and I’m often surprised when I have other listeners give impressions, because I usually have expectations on how they will respond to various setups.
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