I liked the ubiquitous Skull candies, crappy ewrbuds etc. My first pair of decent phones was the Sennheiser HD215. I still have them, and the only other headphones I've bought since then have been the MDR 1R and the MDR V55 (Sony fanboy much?).
I plan to get some IE8s and some HD650s in the future.
What I like about your above posts is how we're reminded that not everyone here has $5000 phones or even necessarily a desire to have them. And this is no slight against those who do, certainly your wealth and hearing capability probably exceeds mine, but it's nice to remember that this is a community, and therefore, one that spans listeners of a variety of headphones across a variety of price ranges.
For me, it was the Sennheiser HD555s. I loved those babies, though I'm sure my recollection of them, based on feelings, is false since they were my first "good" pair, and therefore, really opened my eyes (ears?). It's like that TV show you loved as a kid, and then watched again, and it turned out to actually be really hokey and lame. Not saying the HD555s are lame by any means (though I did not like the HD598s at all when I bought a pair a year or so ago), but I haven't heard them in years and I would rather like my fond memories to stay intact if possible.
Next, I got a pair of AKG K701s, which were nice, if uninspiring out of my LD I+. After that, I moved to IEMs and got X10s and TripleFi 10s, which I use now and have had reshelled by Fisher along with the other 768273286234 people who also had them done.
My current headphones are a pair of Magnum v4s I built, though I'm looking to buy an HE-400 once I figure out what amp I would want to drive them.
That's true about the first pair seeming lame. My V55s sound good, but nothing compared to the 1Rs. Once you go higher up into the realms of Hi-Fi headphones, everything below seems pale in comparison.