
Sennheiser
HD 560S
Budget gaming king with clear sound, but tight fit.

Running these analyses costs money. Buy through my links to help keep lights on! I may get a small commission.
HD599 lover here. I have a lot of headphones and IEMs: Meze 105 AER, 105 Silva, Empyrean, Elites; Focal Bathys, Azurys, Clear OG; Grado SR80X, sr325x; Sennheiser HD380 Pro, PC38X, Hd599, Momentum 4, Momentum 3, Accentum; Bose, Sony, Master & Dynamic, Bowers & Wilkins… and more. And the HD599’s are my daily drivers. They’re what I base my opinion about everything else on. The other ones that compete? Meze105 Aer, Grado sr325x. So yeah. I get it. Enjoy :-)
1. Comfort. Simply put, great comfort all around. 2. Smooth vocals, big focus on them. 3. Scales well with amps. I use them with my Blue Yeti mic most of the time. But when I’m listening to music, I switch to the iFi Go Link or the Chord Mojo 2. These both sound great, especially with a bit of bass boost. The comfort and vocal focus are why they’re my daily drivers at work: I spend all day listening to voices so the smooth vocals are of utmost importance. The PC38X are great at this, too, but not as comfortable. The music performance is a great bonus, and it’s why I often swap the HD599 for the Meze 105 AER: it has better musical performance with similar smoothness and comfort. But the ear cups are smaller and I have big ears, so that’s why I like Sennheisers. I’ve been considering the HD550’s which I hear are a solid upgrade to the HD599’s, but I don’t see a real need.
I've used several Sennheisers and I second/third/fourth the HD 490 suggestions in this thread. They're slightly bassier and more exciting than the HD600-series, and *very* comfortable. If you like the open-back sound I also suggest you try something Grado, for example the SR325x is in your price range and very good. I know they're not for everybody, plenty of people don't like their sound. But also plenty of people *do*, so I recommend you try them as they may just be your jam.
I've tried for years to like the HD600s including forcing myself to listen only to them and nothing else for a month. Still no go. I liked the HD800s just fine. But I love Grados. I have the RS1i, RS1x, 325x and original GS1000s. I like them all better than either of the Sennheisers.
Grado 325x will be good
You going to get dozens of subjective and different answers. For me planars are just ok for rock/metal and Ive tried a few. My favourite for the past few years have been the Grado SR325x .
Grado SR325x puts Sennheiser to shame. You will be amazed at the soundstage (3D sound). Unbeatable sonic value for games, movies, and music.

Sennheiser
HD 560S
Budget gaming king with clear sound, but tight fit.

Sony
WH-1000XM4
ANC king, durable, but unreliable mic and touch controls.

Sennheiser
HD 6XX
Legendary mids, durable, but narrow soundstage and weak bass.

Sennheiser
HD 490 PRO
Super comfortable, wide soundstage for gaming, versatile pads.

Sennheiser
HD 599
Super comfortable, easy to drive, wide soundstage, open-back.

Ranked #1
Sennheiser - HD 6XX

Ranked #1
FiiO - FT1 Closed-back Headphones

Ranked #1
Sennheiser - HD 560S

Ranked #1
Sony - MDR-7506

Ranked #1
Sony - WH-1000XM4

Ranked #1
Sennheiser - HD 560S