“Nothing Compares 2 U” is another one of those songs whose cover outshined the original. Everyone knows the version by Sinead O'Connor, with that simple and melancholic video with her face all over the screen. But the song was written and recorded five years before by Prince. In 1985, The Family, a funk band created as an outlet to release more of Prince's music, released their first and only album, the self-titled The Family. "Nothing Compares 2 U" appeared on the album, but it was not released as a single and received little recognition. It had to wait until 1990, when (then unknown) Irish singer Sinead O’Connor arranged it into a worldwide hit, topping charts in her native Ireland, Australia, Austria, Canada, Germany, Mexico, Netherlands, New Zealand, Norway, Sweden, Switzerland, the United Kingdom, and the United States. It also became a top-five single in France and a top-20 in Denmark. The single was certified platinum in Austria and the United Kingdom, and gold in Germany and Sweden. In the United States it spent four weeks at the top of the Billboard Hot 100, keeping Jane Child's "Don't Wanna Fall In Love" from reaching the top spot; in addition, it was a number-one in Billboard Alternative Songs chart and reached number two on Billboard Adult Contemporary chart. It became the third best-selling single of 1990, the 82nd best-selling single of the 1990s, and was certified platinum by the Recording Industry Association of America in April 1990.
The video itself won three "Moonmen" at the 1990 MTV Video Music Awards: Video of the Year (O'Connor became the first female artist to be awarded with it), Best Female Video and Best Post-Modern Video. It was nominated for Breakthrough Video, Viewer's Choice and International Viewer's Choice during the ceremony.
The success of this version led to a clash between Prince and O’Connor. In an interview with Norwegian station NRK in November 2014, O'Connor said, "I did meet him a couple of times. We didn't get on at all. In fact, we had a punch-up." She continued: "He summoned me to his house after 'Nothing Compares 2 U.' I made it without him. I'd never met him. He summoned me to his house—and it's foolish to do this to an Irish woman—he said he didn't like me saying bad words in interviews. So I told him to fuck off." O'Connor said: "He got quite violent. I had to escape out of his house at five in the morning. He packed a bigger punch than mine."