Sometimes I'm doing "critical listening" and I'll repeat the same song many times carefully examining the interplay between instruments, vocals, effects, rhythms, whatever - and intentionally re listening to it over and over so I can concentrate on one specific interplay each time through.
Sometimes I'm just drowning out next doors power tools of vacuum cleaner, and one song on repeat is just as good as a playlist.
But I grew up in the golden era of albums, and I love to listen to a whole album in the order the artist carefully curated them into. I _can't_ listen to a single song off Dark Side Of The Moon, I need to hear the entire album end to end. (And I will stab anyone who plays the songs out of order - let that be a warning to any Spotify engineers or product managers I ever meet...)
The thought alone of playing Dark Side Of The Moon on shuffle makes me shudder. Why anyone would butcher albums that way is beyond me.
Even my own playlists (of electronic music, which doesn’t tend to be released as albums) very quickly attain a ‘canonical’ order to my own ear. It’s jarring when the anticipation of the next track is disrupted.
While I agree and feel the same jarring effect when listening to songs outside their album context, I've accepted that as the past of commercial music. The present and future lies on listening to singles.
I think you're missing out. There's plenty of music that almost requires repeated listening to even begin to appreciate. Leonard Cohen definitely requires this treatment. His texts are so laden with multilayered metaphor you simply can't even begin to unpack most of them by merely listening to them once. A lot of hip-hop also falls in this category, because just like with Cohen, the emphasis is on the lyrics and their delivery rather than the beat.
I have what feels like an infinite backlog of bands and albums I want to listen to.
My quirk is deep dives. I'll discover a new band or style to me, then listen to as much of it as I can. Very often someone's whole catalogue at a time.
I'll occasionally repeat an album many times - recent examples are both Pixvae's albums or Ott's new album Heads (after 8 years waiting)!
No need to make it a goal to try to get through it. Most stuff sounds sufficiently the same anyway that it doesn't really matter. If you enjoy it, press repeat!
We have more material now than we could ever get through in several lifetimes.
No more than once a day per tune, please.