I've had a lot of bad and disappointing headphones but I'm fine with cheap stuff being bad. Different thing is when expensive headphones are bad. Biggest disappointments starting from the worst. Sorry for people who enjoy these, we all hear differently. I included original msrp's. With actual street prices value factors would change.
1.
Flare Audio Reference R1 $777
- Sound was mostly about midrange only, horrible reverbant ringing midrange. Very tight clamp, hard thin earpads, non-detachable cables. Better headphones can be had for $20.
2.
Aedle VK-X $649
- Thin and metallic sounding. No better than a decent $50 bluetooth headphones. Some usability issues, not great comfort, technical problems. I opened the headphones and they had made no attempts to deal with acoustic issues with all the electronics inside. For 1/10 of the price these could have been cool because of the nice materials and unique looks.
3.
Bowers&Wilkins P9 $899/€899
- I don't think this was downright horrible but not competitive at all with other much cheaper stuff. Bass was bloated and mids horribly recessed. I'm fine with bassy headphones but I think P9 did poorly on controlling resonances within the cups. I like JVC dx1000 so I have no problems with the housing not being perfectly dampened. B&W just did not do it well IMO. Someone described P9 sounding like loud loose farts underwater and to a degree I agree. For a $899 headphone thats not good at all. Build felt like a downgrade from P7, a lot of plastic and dyed leather parts can't keep their color.
4.
Beyerdynamic T5p (gen 1) $1295
Treble mess. I know beyer house sound is not for everyone but I think T5p is particularly bad. It would have been different if the treble was even remotely clean which it's not. For original price this headphone was just plain bad. I quite enjoyed original T1's though. T5p's just is not nowhere as good closed headphone as T1 is in the open category.
5.
Ultrasone Signature Pro $1299
Not a particularly bad headphone but did not excell at anything. Besides fancy glass on the cups the material and design did not match the price tag. Could have passed for a $300 headphone both sound and looks.
6.
Sennheiser HD700 $999
Has same problems as HD800, introduces some of it's own issues and does not really have
whats good on hd800 or hd650. If it were $500 on it's initial release it would have been passable as a brighter more spacious sounding alternative for hd600/hd650. For $999 it's a joke.
Edit: hah! Just realized how anti-european my list is. 3 headphones from Germany, two from UK and one french.