$7.50 Koss PortaPros
$200 (6 years ago) Sennheiser HD595 - good clarity but crap bass (yes they are amped) and have recently fallen apart.
$300 Ultrasonn Pro750, great sound in a full size for that kinda of money, this also takes into account the beating they have taken and still look new. (they also do play down to 20hz - starts rolloff around 50-60)
$1099 My pride and joy - JH Audio 13 Pro's. You will not get this kind of bass anywhere else, it is fast and tight and full, perfect, so is the mid range, so is the treble. The ONLY downside is the soundstage isn't that wide since they are IEM, but since they block out so much noise you can lower the volume signifigantly. MOst current studies also agree that sealed iem are better for your ears for this reason.