Quality, yet affordable headphones for under a $100?

That defeats the purpose of having decent speakers. If I purchase some good speakers for my pc and plug the phones in to em, will that be enough to get a "satisfactory" sound from this personal crapbox?

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Not worth it, even if you could find one for a laptop.

Cool, didn't want to hassle with that mess anyhow. Basically what I would like to know is if some decent headphones would increase the quality of sound when I play cds through my pc? This is primarily needed for 3am usage, as I listen to music via stereo the remainder of the time.
 
Sennheiser for life, though I am looking to try out some Grado's, particularly the sr60 which is also proclaimed to be a true classic, sub $100. The Grado is open air though, versus the closed design of the HD280pro. The HD280 is spectacular, but after going open air with the Senn HD595, i've had trouble accustoming myself back to the closed nature of the HD280pro. But it has its uses, airplanes, noisy public areas.. I'd never bother with the 595s in a place like that.

There's no denying though that the HD280pro is an excellent gateway choice into the world of top notch headphones.
 
From what I hear, the 595s are about the best you can get from the Senn line without worrying about a dedicated headphone amp, which is why I went with them. What they do to the way I hear music now makes them worth every dollar.
 
Oh SHIT! My dad just gave me his barely used pair of HD 555s. He got a "better pair". These are amazing headphones.