Etymotic ER4s without a doubt. I still use them pretty frequently, but I’ve grown to prefer the Westone sound and the way the westone’s fit my ear canals. (OK - I need to experiment some more to see if I can resolve this problem of comfort with the Etys)…
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First pair that really hooked me was a Shure E3c-n.
They let me hear so many details I’d been missing before, and gave me reason to ensure my digital collection was high bitrate, or lossless. I think I bought a few similar pairs over a 3 or 4 year period , but they never held up…something about the type of rubber coating the cords used being deteriorated by skin oils if I recall from the forums I was in at the time. Now I dont buy headphones of any sort if they don’t have removable/replaceable wiring.
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Campfire Vega’s and later EE Legend X
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A pair of Sony MDR-V6…I bought them in the late 80’s, not long after they were originally released (dating myself a bit). I had no idea that headphones could sound like that! Jaw was on the floor, and I’m pretty sure that I actually said, “Holy Crap!”. 
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Sennheiser HD600s Holy Crap!! But oh so uncomfortable… Been chasing that sound ever since. Oh, the incredible detail. The pure sound…
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Years ago I purchased Sennheiser HD 800 headphones and was blown away. Since then I’ve listened to headphones that have topped them. However, I still own these and they are still serious contenders. The HD 800 is a great headphone that has stood the test of time in my humble opinion.
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When i switched to the Senn HD600s back 1998 from the HD 580s… Wow was all i could say…
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The first headphone that that I bought was a huge upgrade from $5 over ears it was a Pioneer Monitor 10 listening to it through my Pioneer SX-750. Once I got my first Amp I was blown away, and its still one of my favorite headphones Aesthetically. Recently I had a chance to audition thoroughly the LCD-4 and HE1000V2 and i was impressed by both and cannot make a sound choice on which of the two I’m gonna get once I save up the money.
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Koss pro4AA showed what was possible, Stax electrostatic bought out the words…Never owned the Stax always too expensive(even as a Stax dealer employee) and fragile.
I’m also a fan of the sound of the LCD over-ear family of Audeze products. Very comfortable padding, yet the weight is too much for me to enjoy them for more than 15-20 minutes. The MX4’s are a step in the right direction (I spent ~25 minutes with a pair at my local dealer/pusher), but I prefer the weight of my headphones to be expressed in oz. not lbs! 
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Sennheiser HD600’s uncomfortable? Interesting…I rarely see them described that way. They are one of the most comfortable sets I own…but I guess everyone’s heads are different. :O)
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Thinksound MS01’s for me. Bought them when I had saved enough money in college and absolutely loved them. Still my go to IEM at work.
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Well said!
One benefit of a heavy pair of headphones is that it forces good posture. I can only hold a slouch for a few seconds with LCD-4s on my head.
Hey dstill77. I appreciate your post because I’ve often wonder whether or not I can justify buying a pair of headphones that cost over $1500. No doubt they would sound amazing, but there’s a diminished return on investment for headphones that cost more than $800-$1000 in terms of how much better they sound (or at least this is what I’ve been led to believe).
What headphones have you owned that you found to be exceptional for the price? I’ve never heard anything better than my B&W P7s–which I find to be quite good considering they’re wireless and don’t require an amp to run.
For what it’s worth, I’m currently looking at Oppo PM-3 and Mr. Speakers AEON.
Fisher Audio FA-004. These are what made me get into headphones
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Bang and Olufsen Form 2, purchased in 1992, didn’t even know what a Headphone Amp was at the time but still got outstanding sound from them. I distinctly remember listening to Joy Division’s Closer and being amazed by how much echo those drums had.
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Seconded. The LCD-2 was an amazing experience.
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I fondly remember my Sennheiser HD-580. As an entry level all around set of cans I would heartily recommend it or the HD-600, HD-650.
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Back in 1971 my bother brought home a pair of Sennheisers with the orange foam ear pads and a copy of The Beatles White Album. That was my first experience with headphones. For their time they were one of the best out there.
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First Holy Crap… Well a long time ago with a Jecklin Float… About twenty years ago with the Senn HD600 — and more recently with the Kennerton’s Odin…
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