I think classical fans would revere Schubert's Winterreise in the same sort of terms that poetry fans might talk about Shakespeare's sonnets or Keats' Odes. (I'm really trying to avoid subjectivity here.) The former's total complexity does, of course, partly depend on Wilhelm Müller's verse.
The position with modern pop song is a bit different. Here's a very unsophisticated form in terms of, say, harmony or the technical demands on the singer. On the other hand the role performed by the pop icon has complexities entirely unknown to the art that preceded the technology of recording; production, drama, projection, the use of rawness and technical limitations as a kind of communication, the exposure of the artist's life, the crossover between artefact and biography. No doubt when I listen to Joni's "California" I'm listening to an extremely complex artefact, as complex in its way as Schubert.
The weakness of recorded masterpieces is the way they are stuck in time. However high we esteem it, Blue is and always will feel like the essence of 1971. It's a period piece. But classical music is inherently a performance art, liberated from being identified with a specific recording by a specific individual at a specific time.
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