I'm not sure if this helps, but in my experience with the MX660, MX760, and CX300, I have come to the conclusion that the CX's just don't sound all that natural. Even though the MX660 is slightly recessed in the midrange (the MX760s are better), the CX300 is far worse, and the bass is far too boomy, while the bass of the MX's has an airy quality to them and is much tighter. The CXs also have very strange sounding upper mids; they sound a tad too bright to be natural.
I'm not sure how the CX300 compares with the 500, however. I should also point out that I'm a huge fan of the MX*60 series. Highly underrated, IMHO. The CXs, not so much. Not bad, but just off, and definitely not worth MSRP.
I have both CX300 and CX500, and the CX500 sounds significantly better than the CX300 in every way. I don't have MX660, but I had MX550 and MX500 before and the CX500 (or even CX300) beats them easily.
Is your friend's CX500 new? The CX500 is a bass-heavy earphone. If they are new, the bass can be a bit overwhelming and muddy. After running in for like 50~100+ hours the bass will be tamed and details will come out. Also, while the in-line volume control is convenient, they do change the sound signature when adjusted. I always use the CX500 with volume set to max, and adjust the volume on my iPod instead. The in-line volume is useful to adjust volume quickly when you want to know what's going on around you without taking off the earphones.
There are many faked CX300 and CX500 on the market though. There used to be a guide on how to tell the fakes apart from checking the flaws on the packaging. I recently read that these flaws were fixed on some newer fakes... I would definitely avoid getting the CX series on places like eBay.
+1 on what kjk1281 said about the MX660. I have the 560 & 660 -- the 560 is stronger in the mids, but doesn't have quite the bass extension of the 660. Also the 660 has much better soundstage/separation of instruments. The 560 tends to get confusing as the volume goes up, but the 660 stays clearer, better separation.
I've listened to my son's CX300 a couple of times before he lost them -- they were too bass-bloated, and not much high-end clarity -- just muddy.
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