All of these criteria, through extensive searching on web, led me to the Sennheiser HD 559. There's not a lot out there, but I was able to find enough matches to my query that prompted me to pull the trigger on these. Anyway, where do these headphones fall on the spectrum? The bulleted list I provided above, or the muddy junk some reviewers would have us believe?

Sennheiser HD 559 vs Sennheiser HD 560S - Versus Sennheiser HD 559 vs Sennheiser HD 560S - Versus

My initial impression was rather bad, in fact it was considering returning it at some point. It seemed to be hard to drive compared to what I was used to and would also distort bass pretty bad relatively early. Compared to my expectations anyway, in practice it's not really that bad but neither is it as good as other more expensive Senheiser 5xx. At 50Ω, the HD559 are at the boundary between low and high impedance. While they are not that hard to drive at 95dB/mW (don't be fooled by the 108dB/V given in specs, as the voltage sensitivity is always much higher), most low power devices won't be able to drive them hard, meaning you will only get a medium to reasonably loud volume. Carroll is a headphone junkie residing in Brooklyn. He's a huge fan of Grado, UK hip hop, and the English Language in general. When not testing audio equipment or writing, you'll find him taking photographs or fiddling with circuit boards. I personally don't like leather pads and headbands as they tend to be a magnet for the slightest trace of sebum on your skin or hair (requiring cleaning almost every time you use them) and leather also tends to make your ears get hot after longer periods of use. Of course not all leather pads are bad, but I clearly prefer velour. I used to be active on these forums for years, and I thought I did a decent job of building a mostly endgame system for myself within my budget: Teac HA-501 amp, Schiit Gumby mulitbit, HD 600, HD 650, Shure 1540, DT990/600, and LCD-2F. I even had a Trafomatic amp in rotation before it developed a static. Still never got that repaired, mainly because the Teac sounded so good to me.

Why is Sennheiser HD 599 better than Sennheiser HD 559?

A 9.8 feet (3 meters) straight detachable cable is the only thing included with the Sennheiser HD 559 headphones. Like the other review said, this kind of tuning with recessed lower treble will be much more forgiving to flaws in mastering compared to a neutral or bright headphone which can give the sensation of piercing your ears with some music. Paired with the right source material, the 38mm dynamic drivers make the HD 599 sound good. However, the frequency response we measure deviates from our headphone preference curve, which we consider to work best for the majority of source material and listeners. There’s a sizeable volume bump where the low mids meet with the bass frequencies. While Sennheiser imbues the HD 599 with a favorable curve in the highs (i.e., it’s sort of close to our ideal before 10kHz), the exaggerated low-mids and bass can make that added treble clarity and detail get lost, especially above 10kHz.

Sennheiser HD 559 - Specs and Review | HiFi Specs Sennheiser HD 559 - Specs and Review | HiFi Specs

The earpieces have a foam surround with a velvet feel to the material and the same stuff is used under the head band. As expected, these are a reasonably comfortable set of headphones with the plush velour earpads perfectly sized to fit around my largish ears, providing good comfort. I searched and couldn't find a dedicated post reviewing the Sennheiser HD 559, so I started my own. I apologize if I missed one. So in regard to comfort, for the money you're paying (as of 2023 these are available for ~70euros) you really get very good comfort. The 559 comes in a standard Sennheiser box. Inside, you’ll find the headphones, a detachable headphone cable, and a warranty booklet.Its bass response was better than I remembered, but the muffled lower-treble was obvious. Something was missing in the music and although listenable as-is, once you know the correct tonality of music you wish for more.

Sennheiser HD 558 vs Sennheiser HD 559 - Versus Sennheiser HD 558 vs Sennheiser HD 559 - Versus

The first device I tried was a walkman with modest output power (2 x 5mW) and it was able to drive them nicely without feeling the need for more power. Volume wasn't super loud, but more than enough for casual listening. This sounded promising. If you want neutral sound and have a bit more money to spend, the HD560S is the one to go for, but do keep in mind that one is much harder to drive at 120Ω impedance. It's way better at all aspects, but also about twice the price. The cups are very large and deep, so your ear will stay suspended inside the cups, not really touching anything. Holding the headphones up side-by-side, it is clear that they have vastly different designs. The Sennheiser HD 559’s headband is made mostly of plastic. It also has a super soft cushion on its underside that is coated with a light velvet material. Oh the other hand, the Grado SR80e’s headband is made of metal and is coated with leather. It doesn’t have any significant padding. However I found it to be more comfortable than the HD 559’s headband. Why, you ask? The HD 559 is heavier than the SR80e and hugs the head tighter. The SR80e is incredibly light and doesn’t squeeze my delicate head. It's defintely wider than the HD 650, and most definitely wider than the HD 569. I'd say the sound stage is about on par with the LCD-2F. There's no 3-headed blob here. Sounds pan left and right very nicely. There's no congestion, either. The torture test I put them through is Brian Eno and David Byrne's "Home." The HD 559 passed with mostly flying colors. I also play Rush's Tom Sawyer to hear how the drums pan right to left. No issues here. In lesser headphones, they pan from your right ear, over your head, to your left ear. With the HD 559, they pan through your head. Impressive.I decided I needed to get some new headphones to use in my newly revived system. I'll eventually replace the pads in my HD 600, Shure 1540, DT990, and LCD-2F, but they're not a priority right now, especially if I don't end up using my headphone system as much as I did in the past. Suffering from the slight compression in the upper mids (a recurring theme we’re seeing with a lot of the new Sennheiser models), the HD 559 may not do some vocals justice, but the rest of the midrange remains largely intact, with adequate detail and good clarity. As successor to our popular HD 500 series, the Sennheiser HD 5 model range offers high quality and value in any aspect. Powered by Sennheiser’s proprietary transducer technology including the “Ergonomic acoustic refinement” (E.A.R.) design, which channels the audio signal directly into your ears. Featuring a contemporary design that is both attractive and ergonomic. A real treat for all, who listen to their music with a sense of discovery. Depth and placement are okay here, delivering a sense of soundstage that is present, but far from arresting. This is about what I expected from the entry-level model, though the overall dynamic sound probably lends some improvement to this modest impression. Again the Sennheiser HD 559 headphones can be considered an entry-level audiophile set of headphones with Hi-Fi sound quality.