The enneagram in pop. The delivery, music and lyric of these tracks illustrate the fixations of the nine numbers:

1. If I Had A Rocket Launcher ( Bruce Cockburn) 
Using music for a moral purpose...

2. How Much is that Doggie in the Window? (Patti Page)
She's  thinking about someone else and how she can help them (and the dog).

3. Poker Face (Lady Gaga)
Three-ishly slick, successful pop. It is also about the difference between inner feelings and outer facade.

4. Wuthering Heights (Kate Bush)
A strange and unique song all about jealousy and death.

5. Frontier Psychiatrist (The Avalanches)
Totally eccentric and showing amazing expertise in the layering and mixing of sounds.

6. We are the World (various)
A team effort, reaching out to bring the world together.

7. Don't Stop Me Now (Queen)
Nobody's going to stop a Seven when they're in the mood for partying.

8. No Scrubs (TLC)
Direct, no-nonsense and totally in control.

9. Orinoco Flow (Enya)
Drifting away in Nine-ish fantasies.

Let me know in the Playground if you have better examples.