You don't need to be an Audiophole to enjoy either can, both are Audiophile quality easily once broken in.
I have the 555 right now (used through my NAD amp for PC gaming and music etc) and it's astonishing after a few hundred hours of burn in, it continues to mature too as I now notice the bass is more refined and higher frequencies well balanced.
I have had various cans in the past from Koss to Grado and Technics and sony as well as other Sennheiser models but will continue to drive the 555 cans into the ground and then buy the next model up
The Big difference between Grado and Sennheiser is their target audience.
Sennheiser often cater for the more entertainment enthusiast, someone who likes a wide soundstage so their cans often suit gaming and movies better than anything else whilst Grado are more of a music lovers type of can putting the listener in the front row with a more central soundstage.
My only gripe with Grado cans is the comfort, to get them comfy you will /need/ to do some DIY, pad your own headband and fashion some custom earpads or buy SR80 pads if you have the SR60.
The earpad swap alone from SR60 to SR80 ones slightly changes the sound you hear and the SR60 sounds more like the SR80.
Grado sound quality is sublime though out of the box, you can hear everything and bass is just so powerful but present.
I really liked the Grado but ultimately had to sell them on due to them being terribly fatiguing and uncomfy after a few hours of usage. Nothing beats Sennheiser for comfort, they're extremely light and well padded, you don't even notice they're on your head after a while.
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