20. Borderline (Madonna, 1983)
Something in the way you love me won't let me be ...
The final single off Madonna's debut album, Borderline was the second song of Madonna's record-breaking 16 straight top 10 hits. A pure 80s pop-dance song whose lyrics dealt unfulfilled love, the song is regarded as one of Madonna's greatest classics.
19. Miles Away (Hard Candy, 2008)
I just woke up from a fuzzy dream ...
The final single off of Madonna's eleventh album, Hard Candy, Miles Away is an electronic ballad about long-distance relationships. The song was the clear highlight of Hard Candy, which was otherwise full of mediocre songs.
18. Don't Tell Me (Music, 2000)
Don't tell me to stop ...
The second single off of Madonna's eight album, Don't Tell Me is Madonna's last second single that peaked in the top 10. An electronic song with elements from country songs, Don't Tell Me was a strange song to follow the lead single of the album, but its mix of genres and uniqueness makes it one of her best.
17. Into The Groove (Like a Virgin, 1984)
You can dance for inspiration ...
A song originally made for the movie Desperately Seeking Susan, Into The Groove is pop-dance song that was included on her second album. Lyrically, the song is about Madonna's love of dance and inviting a male to dance with her. Though it was ineligible to chart on the Hot 100, Billboard called it the best dance single of the 1980s.
16. Open Your Heart (True Blue, 1986)
I see you on the street and you walk on by ...
Open Your Heart was the fourth single off of Madonna's widely successful third album. The pop-dance song reached the top of the Hot 100, and was one of the 16 songs in Madonna's top 10 streak.
15. Hollywood (American Life, 2003)
Everybody comes to Hollywood ...
The second single off of Madonna's not-so-well-received ninth album, Hollywood is an electronic dance song with elements from folk-rock (similar to Don't Tell Me). The song and its music video deals with American life and culture. The song was performed at VMAs of 2003, where Madonna kissed Britney Spears and that other girl.
14. Take A Bow (Bedtime Stories, 1994)
Take a bow, the night is over ...
Take A Bow was the second single released off of Madonna's sixth album. The ballad features a more mature sound from Madonna, notably toned down compared to songs off her previous two albums. It opens with oriental strings and deals with saying goodbye to a lover. The song peaked at #1 for seven weeks - Madonna's longest reign at the top spot.
13. Die Another Day (American Life, 2003)
I'm gonna wake up, yes and no ...
The theme song for the worst Bond movie ever, Die Another Day is sometimes criticized for being one of the worst Bond songs. Though the song may not be the best Bond song, it is one hell of a catchy song. Like the other songs on American Life (and her previous two albums) it is an electronic pop song.
12. Live To Tell (True Blue, 1986)
I have a tale to tell ...
The lead single off of Madonna's third album, the song was used in Madonna's then-husband, Sean Penn's, movie At Close Range. The ballad peaked at #1 on the Hot 100 and displayed a much more mature sound and music video from Madonna. The song is still considered by many Madonna fans to be her best ballad.
11. Drowned World/Substitute For Love (Ray of Light, 1998)
I traded fame for love without a second thought ...
The opening song to Madonna's seventh album and her Drowned World Tour, Drowned World/Substitute For Love is a simple ballad with very minimal electronic music. The lyrics deal with Madonna's desire and experience with fame.