How would you introduce contemporary western popular music?

I have a guitar student who evidently has no experience listening to western music and wants an introduction. Simple enough, but the more I think about it and try to put together a playlist, the more difficult it seems. So here's what I have so far. I wanted to represent a lot of different eras, but also present guitar material that I am comfortable teaching to (jazz, blues, folk).

Prelude No.1 in C from the Well Tempered Clavier (easy enough)
Traumerei, Scenes from Childhood, Schumann
Blues (Jam) - Charlie Parker (14mins of some bootleg blues jam, great stuff though)
Bridge Over Troubled Waters - Eva Cassidy
I Dreamed a Dream - Les Mis
Lady Stardust - David Bowie
Good Hearted Woman - Waylon Jennings
Levon - Elton John
It Could Happen to You - Miles Davis Quintet (Relaxin)
Walk of Life - Dire Straits
Chega de Saudade - Elizete Cardoso
Stella by Fleshlight - Ella Fitzgerald
Le Prochain Amour - Jacques Brel
Linus and Lucy - Vince Guaraldi Trio
Hazey Jane 2 - Nick Drake
Looking into You - Jackson Browne
I Got You (I Feel Good) - James Brown

I deliberately excluded hard rock, punk, hip hop, etc. because I don't listen to it. I listen to pussy music. Also this is all from my own collection.

Anyway, what I'm looking for are ideas of "fundamental" popular music genres the I've missed say pre 1980. British blues comes to mind. Also bebop, hard bop, post bop (which is my real wheelhouse) etc. could see more representation. Maybe too much singer/songwriter?

Bonus points if it lends itself to solo guitar arrangements.