Quote from Quickman

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I currently own and use 599 and 560S every day. 560S at home and 599 at work. 560S are a little clearer and more detailed with a slightly wider soundstage.

599 are warmer and a little more fun to listen to, mainly because they have a bit more bass. Female vocals are a tiny bit more "veiled" than the 560S.
560S are some of the most ridiculously precise and accurate headphones in this price range. Great for games, content production, etc. But for music enjoyment 599 are a little more relaxed, fun, and warm.

Ultimately the differences are minor, so if you have one, I wouldn't be jumping urgently to get the other. If you have neither, you'll get amazing mileage out of the 560S and they'd be my recommendation. In my opinion, the next meaningful upgrade in Sennheiser's line if you want a similar sound is 660S2, so these are an incredible value. I think if I ever upgrade, it would be to at least a 650 or possibly a different brand. But then I'd likely need an expensive amp because most of those have much higher impedance.

Disclaimer: All of this is my opinion as a big headphone enjoyer and someone who has listened to many while working at an audio store.

Thanks for the detailed opinion. As someone who used to have a fairly high end stereo system (Bryston 4BST amp, Adcom 550 preamp, Infinity Kappa 8, Denon 2560 CD, etc) I know what good sound is, but am also price conscious. I've owned the 598s for many years (paid $100 for the brown/ ivory) and picked up the 599s because they were too cheap to resist-- $80. Most reviewers rated the 599s as better than the 598s. I feel the 598s are more open and more pleasant to listen to overall, with better mids and a bigger soundstage, but lacking the bass that the 599s have. I had already added a tiny portable headphone amp made by Brainwavz, who no longer makes them. I got it for $16 on a slickdeal about 12 years ago. It adds a little volume and a little bass and is incredibly clean. With the amp, the 598s have at least as much bass as the 599s, only tighter. It's a shame they stopped making the Brainwavz amp.

So to me, the 598s with the Brainwavz is the superior sound, but at $80 for the 599 I get to keep a pair near the TV. I bought a small bluetooth receiver that has a headphone jack so I can use them with the TV (which has no headphone jack).
I don't intend to get the 560s but I was curious.

Sennheiser HD 560S Wired Over-The-Ear Audiophile Headphones (black)

$150

$275

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