For IEMs I'd look into: Soundmagic PL30 Sennheiser CX300 Head-Direct RE2 Nu-Force NE-6 (These would be my choice, I ran and went to the gym with these for around 2 years before I upgraded). For full-sized headphones I'd look into: Grado SR60i or SR80i - These are pretty much made for rock, I'm just mentioning them because at the price point they are pretty good. They have a little more bass and mids than the MS1s and present the music in a front-row kind of way. Hard to explain, I like them but not for rap music. They sound phenomenal with rock/metal and things of that nature. I personally love the Grado Sound signature. They are open headphones so other people can hear what you are listening to. Alessandro MS1 - It's pretty close to the Grado sound signature, but a little brighter. It does better with other types of music like Jazz and classical and not just rock like most Grados. They are open headphones so people will hear what you are listening to. Sennheiser HD555 - These are fairly neutral, the bass is there but it's pretty far behind the mids. These are also open headphones. Denon 1001k - Closed headphones will generally give you more bass and keep your music to yourself. These are probably my favorite closed headphone in the sub-$100 price range. Audio Technica A700 - Closed and in the price range ballpark. Pretty decent soundstage, a lot of people like them. Sony MDR-V6 - These are pretty popular studio headphones, they are closed. These do well with most things, they don't have a very large soundstage though so classical music sounds off. That should get you started. I'd read reviews and impressions from other people on Head-fi, Amazon and the like.