It depends.
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...)