As the title says, what pair of headphones got you hooked on this hobby and is the cause of your wallet crying to this day?
I got to try out a pair of Andrew’s Sennheiser HD 650s when I was 19 (about 8 years ago) and they were jaw dropping. At that point I had one of the first pair of in-ear Beats and the HD 650s blew these out of the water and starting me down this path.
Not only did it lead to me to spend a bunch of money I didn’t have on headphones and related accessories, but it also set me on the path that would lead to Andrew and I opening a headphone store!
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Focal Clear Professional. And I don’t own them—despite being an audio professional and studio engineer, paying 1700 bones for a pair of headphones strikes me as more than a little absurd. But the clarity, frequency-range, robust bass, transparent highs, lack of any “granularity” (that’s the best word for it) in the mids… Frickin’ amazing. And I should add that I’ve owned or used sooooo many headphones over the years.
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Hifiman HE-500’s, if only they were more comfortable I’d probably still own them and saved myself $1000’s on the endless hunt…
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PSB M4Us - too bad they murdered my giant head. Had to return them.
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Have you had the chance to try the Clears?
I haven’t heard the Professionals myself and was hoping to hear the difference. I quite liked the Clears, especially over the Elears so I was wondering if the Professionals were tuned differently.
20 years ago I purchased a pair of Grado SR-60s and plugged them in to my CD Walkman. It was, no exaggeration, a revelation. My wallet hasn’t been the same since.
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I had a pair of Beyerdynamic DT1350s. Was just floored at the details and separation. Clamp was something to get through, limited my time to maybe a half hour before I had to take them off…
The SR-60s are still legendary to this day! Grado doesn’t seem as popular today but it certainly would be nice to see a Grado resurgence in the next couple years.
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If I could only have one pair of headphones, then it would have to be a pair of Grados. Probably the SR-60 as they are so easy to drive. They are not the most comfortable headphones nor the coolest but for me they are hard to beat for enjoyment/$.
I’ve own several inexpensive headphones throughout my life, from sony, jvc, Phillips, etc in both over the ear and in ear types. It was not until I purchased a pair of audio Technica m50s that I realized what I was missing. That purchase lead me to hires audio, and will probably end with me getting into vinyl records.
I don’t know if spending thousands or hundreds of thousands of dollars on audiophile level equipment is ever necessary, but a few hundred is definitely worthwhile.
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Audeze LCD 2 did that for me.
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Shure SE535s were the first decent pair of headphones I ever owned and I’ve not had better since.
I get the feeling, however, that I will now be hard pressed not to pursue a successor. 
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Sennheiser 800 S. First impression blew me away. Never had heard that kind of “holographic” sound in a pair of headphones before. Sadly, I returned them the next day because they were horrible uncomfortable for my head.
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Focal Elear. Went through quite the odyssey. Started with the Shure 1540’s, then upgraded to the Fostex 610’s and then ended with the Elear’s. No regrets; a fabulous pair of headphones.
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Many years back it was the Sennheiser HD600s. The very first headphone to make me close my eyes, bob my head and tap my foot! I was all-in after that.
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For me…It’d have to be the Audioquest Nighthawks…Have had so many different headphones but for the $ in my opinion the Audioquest headphones can’t be beat 
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My first “holy crap!!!” was for an Audio-Technica AD2000 driven by an Earmax Pro amplifier.
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Focal clears I have grado 60s