Why I'm OK with any winner:
Always Be My Baby - One of the most important songs of my childhood. My AVI

Still played all the time.
Can't Let Go - Many ballads were done wrong, so this can represent them all. The bridge
Emotions - The whistle notes. My ATRL username. Guaranteed she wouldn't suffer from the sophomore slump.
Fantasy - The sample? Music video is cute? It's importance to the decade of music that followed it.
The Roof - Her best song lyrically. Represents Butterfly as its last remaining song.
Vision of Love - Perhaps the most iconic song since it started her career. The vocals.
We Belong Together - The climax. Turned her back into a superstar.