[ZaWorld]

I originally bought the DT 770 PRO 80s to listen to EDM music. While the phones contained plenty of bass, I felt it was missing something important. I assumed I did not like the closed sound signature of the DT 770s.The phones sounded unnatural and most importantly gave me a lot of fatigue listening to it.
 
I assume an open air headphone would alleviate the pressure bubble I experienced. I understand that open air headphones will most likely contain less bass. The goal for this upgrade is to bring out the listening experience of genres such as NU Jazz and Trip Hop. Refer to this youtube channel for examples
 
http://www.youtube.com/user/Bob42jh
 
Current setup is the O2/ODAC. Any input would be welcome. 

 

[NA Blur]

This is going to sound silly, but honestly is a good option.  Go get a pair of Philips Cityscape Downtown headphones.  They are on-ear, but remain quite comfortable, and remove any fatigue.  They have great bass and actually measure really well.
 
Take a look compared to a Denon AH-D2000:
 
Denon AH-D2000
Considered one of the best if not the best closed headphone
http://www.innerfidelity.com/images/DenonAHD2000.pdf
 
Philips Cityscape Downtown
For the price they sound and measure amazingly well
http://www.innerfidelity.com/images/PhilipsCityscapeDowntown.pdf
 
I think the only thing keeping these headphones from being noticed more is the price and the color choices.

 

[Mad Max]

Consider Ultrasones as well.

 

[ZaWorld]

So you both believe the fatigue is not caused by the closed nature? What is it that I hate about the DT 770s then, because these headphones are well known for its comfort.

 

[NA Blur]

Fatigue can certainly be caused by a sealed enclosure.  I can hardly listen to my Denon AH-D2000 anymore after listening to the Downtown.  The sealed enclosure causes all sorts of pressure build up not to mention if the headphone is a tad bright you add in even more fatigue.
 
Ideally you will want a darker headphone ( less treble more bass ) and something that is not sealed to fully alleviate fatigue and still manage to listen to music at a decent loudness.

 

[GaryPham]

Maybe I was just unlucky in my pair but I did not enjoy the Philips Downtowns at all when I owned them.  I found them to sound congested and distorted quite easily at high volumes.  Maybe mine was just an exception since most people seem to like their sound quality.  The D2000s, however, are by far the best closed headphones I've owned so far (and you can look at my profile to see all the headphones I've owned).  Another good option if  you want a comfortable pair of closed headphones that aren't fatiguing at all are the MDR-1Rs (I have mine for sale right now if you're interested).

 

[ZaWorld]

I think I will explore dark open headphones based on all your suggestions. I may have to buy a different amp if I want to bring out the musicality of the cans.