How revealing are Grado sr-60s'?

Yes, most of the music I listen to is some sort of rock, with about 25 percent classic rock- stuff like Zeppelin, Black Sabbath, Iron Maiden and Metallica. I know these arent the best recordings, but shouldnt they at least sound somewhat smoother with better equipment?

One more thing I noticed with these headphones ( and every speaker ive owned as a matter of fact) is that I have to turn them up way too loud to make them open up, by this point the sound becomes too unbalanced for me to handle. It may be my hearing as I have big ears and have REALLY sensative hearing.

I don't know those headphones, but Grados are supposed to be excellent at their price points. They might be just revealing the flaws in your amp & CDP--sometimes happens when you upgrade one component.....

*do i really have to buy a $500 cdp and headphone amp to get good sound out of $70 headphones?*

I have listened through more than one pair of Grado SR-60's, and there should not be any sense of suffering when listening to a good recording through these fine entry level headphones. But, as Bignerd100 stated, you can hear too well the marginal quality of some recordings, and some headphone jacks. There can be some variations in perceived frequency response due to unit variation, shape of ears, or shape of foam earpiece covering. Just a little plastic surgery on the phones or the ears should correct all that :>)
Also, could any of your personal perception of sound have been modified by exposure to very high sound levels at live rock concerts, or high volume headphone listening, earlier in life?
Finally, there is a new product from dakiom.com to optimize headphone output from the simple jack output on any player. Although at $100 (home trial money back offer) it is more costly than your particular headphones, it is intended to demonstrate how much more unexpected sound quality there is waiting to be passed through any headphone output jack.

I'm only 21 and have never been to a concert before. Maybe because im so young and my hearing is still good that these headphones sound bright to me. I bet to an older person with hearing damage bright speakers/electronics would sound normal since the brightness would make up for the hearing loss.

Either way it sucks having good ears and being broke =(

I don't think the Toshiba is a good match for the Grado's.
You shouldn't have to spend $500 on a front end to get decent sound out of them.
I get good results with a portable Aiwa (XP-EV501R) cd player that I bought off ebay for $30. I have read that a $60 Sony portable sounds similar to it but I don't recall the model #.
Instead of the Toshiba, I would also suggest auditioning the Pioneer DV-578a universal player, which sells for $100.