My first experience of a headphone was the stock item that came along with a $99 Sony Walkman in 1985. That sense of wonder has never left me.

My first serious headphone was an Etymotic ER4-S driven off a Headroom amp. loved it.

HQPe on i9-12900k/3080 → Fitlet2/HYPSOS → Holo May KTE → Pass XP-22 
Enleum AMP-23R → Susvara / Salk Song3 BeAT
Pass XA25 → RAAL SR1a
Ferrum OOR/HYPSOS  → ZMF Atrium / Abyss AB1266 Phi