What's an album or song that illustrates the human experience?

I think the intersection of classical music and the popular music of the time is endlessly interesting. What is your favorite piece of music that is inspired by classical music/blends classical music with the popular music of the time?

What's your favorite 3-5 album run from the same musician? Any musician can make a great album, but making 3-5 8+/10 albums in a row is a feat few have accomplished.