There’s also the matter of familiarity — if you’ve already heard a song on good gear many times, your brain will fill in the gaps even on bad playback equipment

There’s also the matter of familiarity — if you’ve already heard a song on good gear many times, your brain will fill in the gaps even on bad playback equipment, but finding new stuff might not be as enjoyable because much will be left out, like bass textures, interesting things happening with sound staging, and even entire bits of melody or background that aren’t easy to pick out with smartphone / laptop / normal car speakers. Edit: the car case is particularly funny as many luxury brands offer $$$$-$$$$$ options for better sound systems when they can’t solve the fundamental flaws of compromised placement and background noise inherent to cars. That McIntosh system in your new $120k Jeep Grand Wagoneer might impress the neighbor but it still won’t do much to quiet the roar of real all-terrain tires on the highway.