25. Sinead O'Connor – Nothing Compares 2 U (1990)
Total Points – 421
Charts – 3
Top 40 – 0
Top 20 – 1
Top 10 – 1
Highest Ranking – 4
This Prince song was originally written for the band The Family, which was a restructuring of the band The Time after Morris Day left. The Family was put together by Prince as a way to record more of this large library of songs. This song was part of the only album they recorded but it was never released as a single. Sinead, reworked the song to explore the feelings of longing from the point of view of the abandoned lover, and it lead to commercial and critical success. The song reached #1 in Australia, Austria, Canada, Germany, Mexico, Netherlands, New Zealand, Norway, Sweden, Switzerland, the United Kingdom, and the United States. It topped the Hot 100 and the Alternative Chart, and it reached #2 on the Adult Contemporary Chart – held out of #1 by Rod Stewart’s “This Old Heart of Mine”. The video was also a huge smash winning 3 MTV video awards, including Video of the Year, which made O’Connor the first female to ever win that award. At the end of the video, two tears run down O’Connor’s face, according the singer, those tears were real, stating that she learned to channel her emotions into her singing through the “bel canto” style, which is comparable to extreme method acting. Sinead, known for her confrontational nature, recorded Prince’s song by herself, and to that point hadn’t even met him. He summoned her to his house and told her that he didn’t like her using bad words in interviews, her response was, unsurprisingly – Fuck off. At which point things turned violent and she had to flee his house stating that Prince packed a bigger punch than she did. This song was the third biggest hit of 1990 behind only, Roxette’s “It Must Have Been Love”, and Wilson Phillips’ “Hold On”.