21. "American Pie" (2000)
Don McLean's classic tune got the Madonna treatment for inclusion in the movie The Next Best Thing. The movie flopped, but the song did well -- reaching number one in the U.K., Canada, and Australia, among others. Oddly enough, although the song wasn't released in the States, it reached number 29 off airplay alone.
22. "Music" (2000)
"Music," Madonna's twelfth single to top U.S. charts, was in the running for a Grammy for Record of the Year, but lost to "Beautiful Day" by U2. The video featured Madonna (five months pregnant at the time) and comedy star Sacha Baron Cohen. "Music" has been featured in all of Madonna's shows since its release.
23. "Don't Tell Me" (2000)
When "Don't Tell Me" went gold, Madonna tied The Beatles for second place for the most gold, platinum, or multiplatinum singles -- a total of 24 -- trailing Elvis, who's way ahead of the pack with a whopping 52. "Don't Tell Me" made it to number four on U.S. charts, and the video shows Madge hanging out with cowboys and riding a mechanical bull. Yee-haw!