For me, there are three trilogies in her catalog that stand out. These don't constitute my favorite or her biggest or best songs, but they go together and are sonically connected. I listen to them together often, and would work (or have already worked) together well on stage:
1. Holiday
2. Get Together
3. Celebration
1. Vogue
2. Deeper and Deeper
3. Holy Water
1. Borderline
2. True Blue
3. Dear Jessie