This thread has so much win...
It's not paintwerk, but my current path is shaping up like:
Nintendo Gameboy Earbuds (I was 12...) -> 1990s Sony Walkman Earbuds (got my first cassette Walkman at a pawn shop in high school) -> late-90s Nokia Craptacular Earbuds (my first cellphone) -> Denon AH-D950 (out of college, making some scratch, wanted decent sound, saw them in Best Buy and thought 'what the heck' ... also wooed by the 'oxygen-free copper' cable, my first) -> Senn HD650 (dropped $385 on a pair of headphones and thought I was insane) -> [spent many years and many thousands of dollars on loudspeaker listening solutions from Rotel/Paradigm/etc.] -> [pursuing the dream, founded my own Hi-Fi business] -> [heard the Abyss at CES2013 and decided they were the best headphones ever... but oh, what sticker shock!] -> Sony MDR Z7 (heard at RMAF 2014, fell in love, ordered as soon as I got home) -> Audioquest Nighthawk (heard at CES, very different tonality than the Z7s, but I want to give them a longer listen... waiting for my first pair to arrive later this week) -> [still hoping to get my ears in between a pair of HiFiMAN HE1000s in the not too distant future... the Abyss are truly an amazing feat, but if the HE1000s even half as good as what everyone is saying, I could probably die just as happily having owned a pair of them instead.] ;-)