#1) Koss Portapro -easily the best headphones outta the three working pairs I own that I even count as headphones, and they'regoing to be my go-to phones from now on because they sound so good, plus they look cool and are actually really comfortable once adjusted right. Foam earpads do tend to get a little itchy, but that's not the phones' fault, foamies in general tend to get a little itchy.
#2) V-moda Bass Freq -decent IEMs for $20, but a little heavy on the lows, and the highs tend to be a little on the harsh side, plus IEMs tend to feel weird in my ears after a while.
#3) Sony MDR-V150 -they're OK closed-back supra-aurals for their price point, their sound is more than acceptable to me, as they were only $20, however the Portapros definitely blow them outta the water as far as sound quality goes. On comfort, they're good and comfortable for a few hours, but then they start to hurt after a while, and as far as durability goes, left headband snapped at the left adjuster on the bus back in August right when I was putting them on, however that was nothing that a crapton of tape on both the side that broke and the side that didn't couldn't fix. All in all, they're pretty much a good $20 set of closed-back on-ears, nothing special about them.
I do however wanna get my hands on either some SR60s (the original flush-housing SR60s, not the SR60i's), some MDR-V6s/7506s, or some ATH-M50s at some point in my life though.
I also have some earbuds that came with my Sansa Clip+, but I don't even count those as headphones, because stock MP3 player earbuds pretty much universally suck balls.