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What was your Ah ha! moment in becoming an Audiophile?
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I started my journey with the original Grado SR80 (before the i and e revisions), back in my youthful days when I thought an icepick to the ear was good sound... but you see, that piercing quality actually opened my eyes (metaphorically) to "hearing things that I've never heard before". Despite several decades of classical music experience, I had untrained ears in the art of listening. The sharp pushy characteristic of the Grado gave me that nudge to start understanding what to listen for.
Nowadays, my ears are bit more "civilized" and sensitive to sound, and no longer need the icepick/sledgehammer approach. I lean more towards the Sennheiser and planars camp these days. I understand that old adage of the Sennheiser "veil", which is not so much a characteristic of the brand but rather that most other headphones have accentuations that are unnecessary.