Quote Originally Posted by Woochifer
If you can bump your budget by another $20, you should also look into the Grado SR60. Easily the best pair of cans in that price range that I've ever tried. They're ugly and not the most comfortable headphones out there, but the sound quality that they deliver for the price is well worth those trade-offs. Grado also recently introduced the iGrado wraparound headphones specifically for the iPod, and those sell for $50. Haven't heard them before, but they do share the same driver as the SR60 (and that diaphragm is also used on their higher end SR80, 125, and 225 models).

Senns are well regarded, but see if you can try before you buy. I once had a pair of the Sennheiser HD500s, and those sounded horrible. I was told to let them break in, but the sound was never satisfying. Didn't surprise me when that line got discontinued.
I think this is excellent advice from Wooch here (and no, he did not pay me to say that). ;-)

The Grado SR-60s are well worth the modest additional investment, IMO. BTW, I actually found them more comfortable than many of the higher-end Grados I moved up to later on, but I guess that is subjective. Just a great overall value for the money that can be driven without the need of a headphone amp and still sound incredible.

---Dave