Top 3 Headphones

Just know what I like and I rarely use headphones. 
Focal Elear open back. 
 

@mastering92 If you are adventurous, you should consider having Mitch Barnett of AccurateSound.ca create a convolution filter for your headphones. You would have to send it to him if he does not already have it. He is a DSP star and is now well known for the convolution filters for the RAAL SR1a. I have them but do not use them since I have the SR1a dialed in perfectly using gear.

Convolution filters are easy to use if you use ROON or JRiver for streaming.

@yyzsantabarbara 

I don't use those filters, but I know what you mean. 

I use Jriver 27 for listening to music with my DAC.

adaptive volume, effects, headphones -> crossfeed, and room correction can be used to create a pseudo-live impression for headphones that lack imaging abilities. Otherwise, I don't use any filters...unless it's EQ for headphones that I beleive require it.

Output is 32 bit 44.1 KHz redbook, jriver bit-exact dithering, play as HDCD if possible checkmarked, input plugin - CDA --> CD read speed 4x, with jitter correction checked.

Lastly, I use Kernel Streaming [direct connection] mode (i2s) interface as the protocol since it's the lowest layer in Windows for audio -->basically like attaching a short coaxial cable between the computer and DAC, since USB audio can handle the redbook audio I listen to with ease.

I would like to add that simply changing the protocol, or any setting on jriver (dithering) for example, will change the sonic presentation to an extent. I have found my above settings to be audibly transparent and suitable for detailed listening sessions.

My three top headphones are:  RAAL SR-1b with transformer interface, the Kennerton Rognir Planar, and JM Audio Editions XTC-Closed.  I have heard (actually not heard) the RAAL CA-1a which are ribbon drivers with earcups and have their proponents of music with foundation, i.e. bass.  I am sure there are others out there but these three are the best I have heard.

Like many here I have owned a bunch of headphones, too many to list ($600-$3000 range). 

Truth be told, I sold them all and kept only the Grado PS500e with F-Cush pads (they increase the bass a bit). They are kind of dynamic like horns. Think of them as the Klispch of headphones. Not super refined but good for the money very dynamic. I chose them over 5 other pairs of headphones that were well over $1k. 
 

My recommendations would be the Grado 80x ($125) to see if you like the Grado sounds or the Grado hemp which is around $350 as these are also the warmer of the grados. The PS500e sounds a lot like the hemp with more refinement in the mids if you use the same pads on each (I owned both at the same time). I am not sure if they make the 500e any more though.

The other headphone I really like right now is the Audeze MM500. This is audeze’s best tuned headphone imo. It sounds much flatter and natural than the older models that have very recessed upper mids (lcd-x) and sound odd. The audeze bass is pretty amazing. Flat extended and very textured.