I've been a long time in the audio hobby, and recently I've turned full-on towards headphones. It looks like I'm working my way through this part of the related Sennheiser headphone family. I bought a pair of original HD-580 Precisions years ago. Never really liked them, even when fed by the best headphone feeding gear I had on hand - a collection of very nice DACs and a Pete Millett tube headphone amp. Too thick, syrupy, slow, dull, untransparent. Later, I spent just a little while with Grado 325s and HD-600s connected to an Audioquest Dragonfly.
I've gotten into headphones in earnest recently. All of a sudden I find myself with a modest collection of headphones - Hifiman 400is, Thinksound ON2s, 1MORE triple driver on-ears, Sennheiser HD-6XXs, and now HD-58X Jubilees - along with some headphone-intended use electronics - NAD D 3020 integrated amplifier, Meridian Explorer2, and Schiit Modi Multibit. I've been tremendously impressed with the quality and the price-performance value of so much of what's available today, and all this kits falls under that.
I'm enjoying the journey today quite a bit, but I still haven't found exactly what I'm looking for, and haven't gotten to the level of palpability of a very good speakered system. I feel like I'm close to what I'd be satisfied with, so I suspect it's out there. These 58X Jubilees get me closer. IF, as is often reported, the driver in the Massdrop Sennheiser HD-58X Jubilee is the same as used in the HD-660S and HD-700, but with different tunings, well, the 580X Jubilee might just be a bit of a reasonable sampler of all three of these headphones.
Mixing and matching my electronics across different types and quality of recordings, my general impressions are thus... The "veil" I've known from the original 580 Precision and the 6XX/650 isn't there with the 58X Jubilee. The high frequencies are more forward and articulated without being bright or over-emphasized, and the bass is also more articulated and extended. That frequency area around the upper bass/lower midrange is less congested, too, compared with the 6XX/650, which can at best give the 6XX/650 a lovely, organic texture, or bloat and muddiness with some recordings.
Soundstage? Imaging? I'll just conveniently pass on these elements here. Headphones are a peculiar kind of animal here, quite different from a two-channel speakered system... Detail and ambiance retrieval and presentation. Very good. It's there. Tonal character and texture. Yep. Plenty good. It's all convincing with nothing that calls out as a gross coloration. Dynamics scale? Nice job here, too.
What I feel I'm looking for is this headphone with more transparency and a more convincingly spaced soundstage. Or a Hifiman HE-400i with smoother high frequency response and deeper bass reach? That would be closing in further to what I think I want. Even though I'm still looking for something a little more, I gave the Massdrop Sennheiser Jubilee 5 stars because it's all by itself and on its own an excellent audio product - sounds great, looks good, well-made, comfortable - at any price, and a remarkable value at the Massdrop price.