“Nothing Compares 2 U,” for all its lush restraint and lilting pathos, was written in the mid-1980s by an artist named Prince. The musician had assembled a band called The Family as a side project and an outlet for his prolific songwriting abilities, and the song appeared on its first and only album as a futuristic soul ballad, with Close Encounters-inspired synth jams and an inspired saxophone solo. It’s an intriguing recording to listen to, but by no means does it sound like a future VH1 staple. Singer Paul Peterson channels the exaggerated regret of the lyrics—Tell me baby, where did I go wrong?—but his delivery is too polished, and too deliberate. As far as feeling bummed out goes, he gives the impression that his weekend has possibly been ruined, but not so much his entire life.

O’Connor, by contrast, offers something more guttural. She’s angry; she practically snarls at the camera and seethes as she recalls a doctor’s foolhardy advice to go out and try to have fun, but a few seconds later she’s desolate again, almond-eyed and hollow. She casts her eyes down at the ground then looks up again, half confrontational, half lost. Wearing a black turtleneck, and against a black backdrop, her head appears to be floating. When she sings, “Nothing can stop these lonely tears from falling,” the passivity of the statement aches. Then, the “nothing” of the chorus is emphasized and bisected as she jumps an octave, underscoring its emptiness.

Then, around the 3:20 mark, after a few shots of O’Connor stalking around Paris in an overcoat, something extraordinary happens. As she sings, “All the flowers that you planted, mama, in the back yard, they all died and withered away,” two tears well in her eyelids and fall slowly down her face. “I know that living with you baby was sometimes hard,” she yelps, “but I’m willing to give it another try.” In her own words:

The close-up of me singing “Nothing Compares 2 U” was supposed to be only one part of the video. But the song reminded me of my mother, who had died three years previously … I made an emotional connection, which I was not expecting—it didn’t hit me when I was recording the song. It only kicked in when I was being filmed. So I was sitting there, thinking about me mother, and trying hard not to bawl my eyes out.

The moment is unrivaled in music video history when it comes to raw emotion, but the song itself is serves as an example of the power of interpretation. Produced by Nellee Hooper, who later worked with The Smashing Pumpkins, Bjork, Madonna, and Gwen Stefani among others, it made an understated ballad out of a funk-pop song, and a star out of its singer, who enhanced her notoriety two years later when she tore up a photo of Pope John Paul II on Saturday Night Live. O’Connor might not sing it anymore, but the work is ultimately timeless—a confession of pain that defies its saccharine lyrics to offer instead one of pop’s most honest performances.

We want to hear what you think about this article. Submit a letter to the editor or write to letters@theatlantic.com.