Best Headphone system under $1000???


Hi all,
I've been a 2 channel audiophile for 30+ years, and I'm ready to liquidate the big system and simplify.
I'm interested in finding a really nice set of headphones and a headphone amp, to pair with my DAC and MacBook based Tidal streaming source.

Interested in staying within the $1000 range (or under) for headphones and a dedicated headphone amp/preamp.
As far as tastes go, I prefer a "musical sound" to the more hyper detailed hifi/neutral sound. I enjoy jazz, funk and R&B, classic rock, and some classical, so I'm hoping for a headphone system that is slightly warm and has good soundstaging.

For reference, my big system has Vandersteen 2CE Sig 2s, Odyssey Kismet amp, and a nice 6SN7 tube preamp from JE Labs. I like the full, colorful, dynamic sound of this rig and hope I can replicate it in a headphone set up. 

Any recommendations would be very much appreciated!
Thanks!
Lincoln
lincnabby
Tried the Focal Elear and Focal Clear today in a shop and fell to sleep. Moved to the Sennheiser HD820 and woke up. Sounded like
my near-fields but a little thin and less dynamic. Very good separation though. Not too much impressed for that kind of money. They all need a special amp. The one used was the Sennheiser HDV 820. Beyer DT990 Pro seems like a good value... 
For those trying out grados for the first time the Grado PS500e is easily their best IMO. It has all the details of the others or more but softens the 2k midrange spike and has a lesser more balanced treble. Makes for a relatively warmer Grado (still bright). Sadly I had to get two pairs to get one with good driver matching. Order from some somewhere you can return them...

I have owned/used the following grados and choose the PS500e.

PS1000e (scooped out mids, they call it soundstage, I call it messed up tonal balance)

PS500e (good, light/fast sounding and punchy like good monitors, a little bright still, I love the close vocals).

GH1 (a lot like the PS500e but more colored mids, you can hear the wood in the bass for better or worse)

GS2000e (uhm no, really bad, just no, ear tweeters, funky soundstage)

RS2e (brighter and less bass than the PS500e, small spike at 2k)

RS1e (I don’t really rember these...)

RS325(pretty bright, probably the brightest Grado I owned, ok other wise)

RS225e (light on bass, more open mids from the models down, a poor mans RS1/2)

RS80e (Best buy, most of the Grado sound for under $100)

RS60e (warmer of the grados. Tuned like the PS500e but less open and detailed acrossed the whole frequency range.

This is fun- haven't created a thread with this many responses in quite awhile. I'm still waiting on my little Atom amp and in the meantime, beginning to surf the web looking at IEMs too. 

Anyone have recommendations for an IEM that leans more toward the warm side of neutral and has exceptional sound staging/imaging?

I might explore this realm of headphonia too, but probably wouldn't want to spend more than $300
Update- with the Focal Elex, the JDS Atom amp, and my MHDT Stockholm 2 DAC, things are sounding pretty damn good. I do have a VD Nite II power cord running into the DAC and a pretty high $ IC from amp to DAC (stupid considering cost of headphones and amp?) but I’d say the PRAT, detail, and immersive soundstage rivals and in some ways exceeds my full size rig. 
Hopefully, I can manage to just relax and enjoy the tunes for awhile!
Update-
I’m officially on the head-fi crazy train now. 
I purchased a Woo Audio WA-6 amp to replace the Atom, and have enjoyed a fairly significant improvement with the Focal Elex cans. In my former 2 channel system I really loved my 6SN7 & 5ar4 based tube preamp, and the Woo uses these same tubes.
 If any of you out there have specific tube recommendations for the WA-6, please share. 

Also, curious if anyone with the Focal Elex has dabbled with cable upgrades?
it may be a waste of money, but I definitely fall into the “believer” category for audible improvements with speaker and power cord upgrades. 
Thank you for any advice. 
I had the Woo Audio headphone amp with two Sylvania Bad Boys and one 40s Tung Sol rectifier Tube, I also suggest you get Herbies dampers for all tubes. 
Would recommend braided (kind of following Kimber cable's philosophy) and look for OCC copper (ohno cast single crystal copper) possibly sliver clad, as well. Enjoy the crazy train! We now grant you an official audiophile carrying card... 
In regards to your question about cables, I have Focal Elex and Sony MDR-Z1R headphones, which both have the same connectors.  I've used a few different cables, mostly mid-grade to inexpensive cables. 

To me, there is not a noticeable difference between cables, which is also my experience with interconnects, speaker cables, etc. 

I buy cables for fit and finish, length, different connectors (balanced, single-ended), not for sound quality.  Which isn't to say that there aren't differences in sound quality, but that unless I A/B them back and forth repeatedly, there aren't differences noticeable enough (to me - your hearing may be more sensitive) to make me prefer one cable over another.  
Geoffkait- I’m actually leaning toward vintage Sylvanias. I had Shuguang Black Treasure CV181z tubes, and they surpassed NOS with my old pre, but they’re very pricey and I’m wondering if it’s as critical in this Woo amp. I bought it used and it came with a Sophia Princess 274b rectifier, which is pretty well regarded, but considering a Mullard GZ34in that spot. Might call Andy at VTS. 

Bstatmeiser and big_greg:
Appreciate thoughts on cable...
I was actually looking at litz braided upocc cable from a company called Dyson Audio. 
About $135 for a 2 meter. 
I can definitely hear clear differences between ICs, PCs, and speaker cable, but it does require lots of A/B tests and tweaking. For me, that’s part of the fun, but I respect those who don’t hear it. They’re saving lots of money!
Once I empty more of my wallet, I will post again with impressions!😀

How would you compare the Audeze LCD 2 against the Focal Elex headphones? They both seem to get good reviews within the price range
How would you compare the Audeze LCD 2 against the Focal Elex headphones?
They are both excellent headphones.  The LCD 2 is going to have more bass and be a little more "rolled off" at the high end (the Audeze "house sound").  They still provide good detail and excel in the mid-range.  The Elex is going to be a little more neutral throughout the frequency range and I find them more comfortable to wear.  Which isn't to say that the Elex lack bass or that the LCD 2 is uncomfortable.  The Elex has good bass response and maybe a little more "realistic".  One of the things I like about Audeze is they come with really nice earpads and are comfortable from that standpoint, but they are a little on the heavy side.

I suggest checking out Headfi and Innerfidelity for in-depth reviews of both.
Don’t know why but I went all in with a headphone setup just recently. I’m a redbook CD guy using Sonos and that’s not going to change - too darned convenient for me.

Sonos > Benchmark DAC3 B (DAC, only - no volume / amp / headphone jack / ..) > Woo Audio WA2 > Sennheiser HD800S.

Kimber Silver analogs and digital cable.

It’s been awhile since I’ve been ’taken someplace new’ with music.

(Also considered the Chord Qutest.  Got turned off by the 'filters'.  I wanted as pure a signal to the tubes, as possible.  I contacted Benchmark and they said to not worry about jitter - the Benchmark will take care of that.  I had told them I have an Empirical Audio PaceCar 2 I could put into the mix).
I would never give up my Stax as they have the best tone of any phone .And IMO that is job#1 in buying any piece of audio gear which is what I use them for .
That said , most of the time I listen to my Audioquest Nighthawks as the are natural sounding and very easy to listen to for hours on end .