I'm right there with you on most of your top 5 albums:
1. American Life (crazy underrated because of the stupid choice of first released single that involved her rapping, lol, and they threw on the ok but not great Die Another Day which didn't fit in with that album)
2. Like a Prayer
5. Ray of Light (possibly her best artistically)
It is near impossible to pick 5 songs. Top 20 maybe? Okay, I'll try:
1. Material Girl
2. Nobody Knows Me
3. True Blue
4. Love Profusion
5. Hung UpI'm trying..but I... just.. can't stop...
6. Human Nature
7. 4 minutes
8. Power of Goodbye
9. I Love New York (yes dumb lyrics but an amazing beat & I do indeed love NYC
10. Jumpstill unable..to..stop..typing songs..
11. Burning Up
12. I'm Addicted/I'm a Sinner (MDNA tie)
13. Till Death do us Part
14. Don't Tell Me
15. Candy Shop/She's Not me (Hard Candy Tie)I give in to the Madonna love..
16. Impressive Instant
17. Xstatic Process
18. I Deserve it
20. Where's the Party/Open Your Heart (True Blue tie)dragging myself away from computer..yes I am obsessed & not good at following rules ;)