THIS. One of the clear weaknesses of contemporary music education in the U.S. at all levels, up through graduate school, is that it does not typically proceed from existing musical interests or contemporary cultural contexts into more detailed and less familiar territory. (There are notable exceptions.) This principle seems essential to me in music education, or any areas of study and work that are strongly connected to cultural practice.
Geoffrey Himes illustrates one way this principle can be applied in his delightful article "Why We Should Teach Music History Backwards." Seriously, this article makes me want to start writing a reverse music history curriculum that would start with contemporary music surveys (popular, concert, movie and game scores, all of it) and work backwards in time, which I think could be fascinating. Call it the "Where Did This Come From?" approach.
(I do realize that this would require a fundamental shift of values in the musical world on all sides, from ones that originate from judgments about means and modes of musical creation to values that emerge from engagement with contemporary cultural practices as they are found. I'm also aware that such a paradigm shift would take over a generation. But, you know, the second best time to plant a tree is now.)