"1. Like A Prayer (1989) - Like the past two songs, it's perfect pop. What elevates this slightly is its wild ambition, both in the music video and the song itself. Choirs, guitars, religious overtones and a new found vocal maturity all add up to her most riveting single."
"3. Papa Don't Preach (1986) - Her first major foray into exploring social issues in her singles. But -- and this is key -- that seriousness didn't stop the song from being incredibly melodic, 100% pop and timeless in production. One of her absolute best."
"4. Hung Up (2005) - Madonna and Abba. It could have gone horribly wrong. But that sample, coupled with the song itself, easily became the highlight of her 00's output. If only she would have continued in this vein for the rest of the decade!"
"5. Ray of Light (1998) - After a muddled output in the 90's (in my opinion), this was the track that brought her career roaring back. Combining elements of her early work (the massive hooks and bright production) with the artistic experimentalism that would define this period of her evolution, it was the perfect musical statement."
"7. Live To Tell (1986) - The first track on the countdown from her greatest pop album, this was the most mature ballad listeners had heard from her at the time. Even today, it's still incredibly beautiful and affecting."
"9. Vogue (1990) - One of her most iconic songs, and ultimately I think it suffers from that a bit. Still, taken on its own merits, there's simply no denying the melody and sound. To me, this is the last release of her greatest, late 80's era."
"10. Music (2000) - The toughest spot on the countdown, because this was battling with several other singles, some much more iconic. But ultimately I chose this because I think it's the best representation of her early 2000's output. And, as silly as it all is, it's actually aged quite well."