What percent of your listening would you describe as “analytical” verses “musical”…do you care, do you chase one over the other…If so why?
Me I’m more music and fun but I can understand detail, technical chasers maybe there’s 
between the two but I reckon it’s a fine line 
Musical and fun all day err day.
90% of the time I’m just listening to music and enjoying it. But that other 10% I’m doing something like pad swapping or testing a new headphone which requires much more analytical listening.
If I change EQ or Lowpass/highpass filter, I’d listen carefully. When I’m done with it, I just enjoy music.
I’d consider details musical, because I admire the musician for paying attention to details.
I really only listen analytical if i get new stuff and compare it to other stuff. All the other time i just listen to have fun, but sometimes i catch myself analyzing a track even tho i thought i listen only for fun. Does this make sense? 
I’m 50/50? When I saw your question I thought that it was an easy answer that I listen for the music. But thinking about it, every time I listen to music, I critically establish the quality of it, how does it sound, where the stag e is, the strengths and weaknesses, things that could improve. What sounds pretty great. So the real answer for me is that I ALWAYS listen with some level of criticality but that I don’t let it impede the enjoyment of the music…
But who knows, that last line may be somewhat of a lie, because the better my 2 channel system got, I have found myself hitting the next button more on shitty recordings, so maybe it’s a hard thing to quantify.
This answer applies only to my desktop and my two channel system. My car, I just listen to the music.
Musical. Last thing I want is an analytical headphone. I listen to music for fun. I’m not an engineer or producer and find overly analytical headphones extremely distracting.
The best analogy I could give is imagine being at a party with 2 friends. One friend you have good, fun conversation with and the other friend won’t STFU no matter what you say or do, lol. I’ll take the 1st friend. If I wanted to be annoyed I’d call my mother in law. 
I would say i mostly would listen for fun, hence musical for me. Also, not sure if any of my headphones are really that analytical in their delieverence (Koss kph30i, porta pro and ksc75, Philips Fidelio x2, Sennheiser HD58X and Hifiman He-4xx).
It’s mostly musical for me. If I get new gear I would be analytical with it for a while until I get a grasp of how it sounds and what it’s good at and then try and listen to music that works well with it in a fun way.
If you’re telling me X headphones or X DAC/amp makes everything sound “better than real life”, I’ll hate it as much as I hate dollar store stuff, because it would mean the same thing to me: It destroys the original music.
I’m a musicophile who wants to hear the truth so the most fun I can have is via analytical headphones and lossless audio. 
I still have, and love, a pair of headphones (Monoprice M650) that, I think, blur everything a bit (compared to planars), but I mostly just use them to relax.
For me it depends. If I’m listening to my more pricy gear I always have some level of focus on technicalities. If they’re not there, some level of enjoyment is gone - after all, they’re the reason I spent the money. The enjoyment comes from the ability of the equipment to let me hear things I normally wouldn’t. The tiny nuances in the music that the artist added that you normally don’t hear. It’s like knowing something that most people don’t know…a secret almost.
If I’m doing chores around the house or yard, the KSC-75 off the iPhone is plenty musical and enjoyable. I can listen to that combo for hours.
I guess it comes down to expectations to some degree - what should the equipment return for the amount paid.
I listen as analytical as I can most of the time, but unless I’m comparing or reviewing the gear its the music that I’m analyzing, not the gear.
This is the way my brain is wired and I do the same when doing “fun” activities like watching movies, I’m constantly analyzing the framing, camera angles, lighting, emotions of the actors, etc…
Only when I’m very relaxed I really get into the music and its more of a “blank mind” and just enjoy the sound state, I believe this relates to my preference for dynamic drivers over planars as they sound more organic and help me get into the music.
Well, I just opened this thread and realized I was listening to Tenacious D…
…on Spotify without premium
…through KSC75 (with higher end gear in reach of my left arm)
…straight out of my phone (no external dac/amp)
And I had a fkin time of my life.
For me it is 90% of the time just about the music and if the gear doesnt make the music noticeably worse (unsuitable tonality for the genre e.g.) I just enjoy what I hear no matter the price tag.
Of course I appreciate the “gear” when listening, but the music is and always will be the focus for me.
@A_Jedi makes a good point. I am always listen for the technicalities of my headphones even when just relaxing. It’s kind of the point of high end audio to hear the nuances of the gear and music.
I think the real distinction is whether or not you are judging/appraising the gear/music for it’s technical performance or if you are enjoying it for it’s technical performance.
Like when you play a video game, you are engaging with and analyzing the systems of that game to get better or progress. The question is are you just playing for the experience of playing or are you playing to review the game?
It is possible to do both at the same time. One could argue that you have to actually. I think some people get confused on analytical vs. something that sounds analytical…2 different things.
Well it depends on how you define these two terms. Personally I don’t think it’s binary or mutually exclusive. Musicality doesn’t necessarily sacrifice the analytical aspect of music provided that the gear is good enough. And I actually find analytical listening produce a lot of musicality just by listening to the amount of microdetails, how music interacts and is represented by the gear, how aspects technical performance such as accuracy, imaging or stage can provide an immersive experience.
For me, if a setup can’t provide both at the same time, then it’s not good enough for me.
On “analytical”, I was primarily using it in the sense of a analytical listening style. But I still don’t think an analytical sound is inherently bad (provided that you don’t think THX or A90 actually represents an analytical sound - they are simply bad; for me studio gear tends to be analytical but also very musical, and good tube amps tend to be musical but also analytical enough)
I disagree. Analytical sounding headphones completely distracts from me enjoying the music. Maybe it is because I’ve been a Musician since I was a youngster, but I just can’t enjoy it at all.
I do agree on the THX and most of Topping’s stuff…sounds awful IMO.
Another caveat…the amount of people that use audiophile terminology, yet have no idea what it actually means is another problem all together.
As I said, it is all personal and subjective. I’m no musician but I did play over ten years of piano from which I have developed the tendency to pay utmost attention to details in the music. A pair of headphones like the Clear enables me to listen to and analyse those details, it does not distract me from enjoying music. It is the way I enjoy music.
If I want to just relax and “hear” the music, I don’t need any audiophile gear. A Bluetooth speaker in the background is enough for that purpose.
Musical.
But I’m kinda weird. I want my sources and amps to be as linear and analytical as possible. Then the actual output gear can be super musical. I think this shows the differences in headphones and speakers more than whatever bullshittery comes out from the amp. One reason why I don’t go higher in quality for headphones and speakers is because I enjoy the differences the lower end provides.