The SoundSport Wireless are wireless sport earbuds that are very similar to the SoundSport Free. Instead of being true wireless earbuds, however, the two SoundSport Wireless earbuds are tethered together by cable. Aside from that, the two wireless earbuds have similar audio performance and use the same Bose Connect app. The SoundSport Wireless will last longer on a single charge (as opposed to the SoundSport Free which recharge every time they go back in their case).
The Astro Gaming A50 emerged in 2012 as the wireless follow-up to the excellent A40. Seven years later and four generations on, they remain the gold standard for gaming audio. With an ability to faithfully reproduce 7.1 channel surround sound through just two earcups, gamers will get critical 3D audio for all of their favorite console titles whether it’s from an Xbox One or a PlayStation 4. Wireless audio can lead to an unacceptable amount of lag, which often sends gamers in search of wired models, but here too, the A50 manage to beat expectations.
I think it’s fair to compare the Grados and HD598, but the M50 is very different and seems not to fit in that comparison. The DT770 is a better comparison to the M50, although the 770 is a better more expensive item. A long time ago I had a Grado 325 and a Sennheiser HD565 – very similar, very enjoyable. Today for that type of sound I might choose the Soundmagic HP100.
What I’m saying here is that it’s better to own three $100 headphones than one $300 headphone. Or three $300 headphones than one $900 headphone. Why? Because most people don’t limit their playlist to strictly one genre. And following the logic from Rule #2, the right headphone-music pairing is going to be better than one expensive headphone paired to the wrong music.

Portability can mean many things, such as appearance in public, having a secure fit so the headphone doesn’t shift off of your ears, amount of isolation from ambient noise (including active noise canceling), whether the headphone can be worn around the neck when not listening or it requires a carry case, and when extra amplification is required, whether a suitable amp can be found that’s OK to carry along with the portable music player.
Earbuds have small speakers that rest on the ear canal of the wearer. These are usually much less expensive than on-ear and over-ear headphones and reproduce the sound well. However, outside sounds, such as traffic or power tools, can get past the earbuds and interfere with your enjoyment. Earbuds also don't stay in place very well if the wearer is moving much, such as exercising. These also are lower fidelity than on-ear and over-ear headphones.
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