Some people backed the wrong horse. Much music exists mastered for old shitty car stereos and earbuds and the like. Sometimes, the original recordings are lost or nobody bothers to remaster them.
And if your equipment is really really good, you can even hear Jason on Justice :).
I do indeed remember how good it sounded. Also had a Sony Walkman, pretty good but nothing like a good furniture-size stereo.
I like to listen to playlists on shuffle and the inconsistency between different albums has me fiddling with the bass on a song to song basis. Luckily my car has steering wheel controls for this. But most modern vehicles would have you fucking with a touch screen which is a non-starter while driving.
This is kind of repeating with playlists now. Not all services normalize perceived loudness across tracks (e.g. Spotify web player).
And related cause: A&R people listening to xyz's new album and judging it sounds "huge" / "phat" / "modern"... when actually it's just a bit louder than the other guys, but nobody's adjusting volumes between demos...