Sony - MDR-R10

Sony MDR-R10 was unbelievably good. I haven't heard recent TOTL stuff, but I have a hard time believing they sound as natural as the R10. Not that I'd ever own one; $15000 ticking time-bomb

MDR-R10 and Qualia 010 are in a completely different league.

Sony is my favorite, and in my opinion the greatest audio company ever. You're asking about wireless headphones and while yes, they've made decent ones, that's just barely scratching the surface. Firstly, they've pioneered portable audio with their N.U.D.E. series of earbuds. In fact, the 1988 sapphire diaphragm [MDR-E282](https://forum.munkonggadget.com/upload/2013/03/20130305211756.jpg) is still to this day the best open earbud I've heard, even when compared to modern flagships from Yincrow or TGXear. They also made excellent headphones not only for pro applications (gold diaphragm [MDR-CD7](https://www.reddit.com/media?url=https%3A%2F%2Fpreview.redd.it%2Fu5mo5uykwkbb1.jpg%3Fwidth%3D640%26crop%3Dsmart%26auto%3Dwebp%26s%3Da9f6a48220e3d1f4b22d06876318cf551b384ea0) on-ear, amorphous diamond diaphragm [MDR-CD900 non-ST](https://lh6.googleusercontent.com/proxy/IBIW8n-XHzclljiF96xS1RCwhguo850br6K7jrXBS5BUYhg7TvoedjyIUR3RneRS8Z1M7zxlzEXLG0wGI1fGev8m1gTnFDc_6pM)) but also some of the greatest-sounding ever for audiophiles, like the [MDR-R10](https://justfriends.jp/imegs/141108/mdr-r10/b1.jpg) (first ever use of biocellulose and the best midrange I've heard in any headphone) and the very unique [Qualia 010](https://www.hear.audio/wp-content/uploads/2018/01/Sony_Qualia_010-22175-1.jpg) (which the Sennheiser HD 800 copied in many ways, from the open baffle design to the LEMO connectors used). Then there's their modern IEMs. The [MH755](https://headphones.com/cdn/shop/articles/42408370_FullSizeRender_1_dcefda2b-2951-417a-add6-71b652ebb6c4.jpg?v=1707862175) (now forgotten) is probably the best IEM you could get under $10. The [MDR-EX1000](https://m.media-amazon.com/images/I/511KHYkLfYL._AC_UF894,1000_QL80_.jpg) was also a huge leap forward when it released in 2010 and still is one of the most technical single DD IEMs ever. Nowadays, [IER-M7 and M9](https://www.sony.ca/image/35fb708577f1e0d67714276b3613b365?fmt=png-alpha&wid=1200) are some excellent mid-fi options. Then there's the [IER-Z1R](https://www.sony.ca/image/73156ef56be3ec543335baa517c39384?fmt=pjpeg&bgcolor=FFFFFF&bgc=FFFFFF&wid=2515&hei=1320), which is probably my favorite IEM ever. And they don't use off-the-shelf drivers like most high-end manufacturers - [everything is developed and built in-house](https://assets.hardwarezone.com/img/2018/08/ier-z1r-1.jpg). Even down to their magnesium diaphragm, silver voice coil BAs which absolutely no other manufacturer uses (they just instead buy generic ones from Knowles). Regarding source gear, they not only made the [first ever portable cassette players in 1979](https://syncoriginals.com/wp-content/uploads/2014/08/walkman1_1436143i.jpg), but are also well known for their now 9 year-old [WM1A and WM1Z](https://i0.wp.com/musicphotolife.com/wp-content/uploads/2017/03/Sony-WM1_3.jpg?resize=1170%2C878&ssl=1) which to this day are still some of the best-sounding DAPs. And that's not even delving into their stereo gear which is where they really went crazy... look at their ultra flagship monsters like the [DAS-R10 current pulse DAC](http://www.thevintageknob.org/sony-DAS-R10.html), [TA-NR10 class A monoblocks](http://www.thevintageknob.org/sony-TA-NR10.html), [TA-ER1 preamp](http://www.thevintageknob.org/sony-TA-ER1.html), and [SS-GR1 biocellulose floorstanding speakers](http://www.thevintageknob.org/sony-SS-GR1.html)... I could go on and on about some of their other great releases but I think you get my point. While modern Sony stuff isn't quite up to the level it was before, they have by far the richest history of benchmark-setting products in all areas of audio over the last half-century.

Sony MDR-R10 and it's not even close

This is the correct answer. Z1R is meh compared to those, and I've heard the R10s.