The Grado GS1000s (as delivered with the oversize bowls) are light and wonderfully comfortable.
The Grado RS1s (only with flats) also feel great (the stock regular-size bowls annoy me).
Sony R10s feel so nice, especially considering their weight. Other manufacturers should copy their earpads (and
physical structure)! Those black pillows are so soothing, you could almost sleep while wearing them.
Dishonorable mention: I had Stax Omegas for years and, although I liked the sound, found them really,
hideously uncomfortable and annoying, with the thin under-stuffed leather pads pressing on my ears.
And the space for your ears was shallow and the rough driver cover would sometimes rub against my ears.
And the headband was hard and pressed on my head.
A real bummer since they were
expensive when i got them new with high hopes back in 1999.
Mysteriously comfortable: Senn HD800s. They LOOK like they would hurt, but somehow they feel fine.
Amazing engineering-design job with that silly looking thin black rubberish surround.
All above IMHO, of course.
Thanks for reading.