May 10, 2026

The Greatest Cover Songs of All-time 5. Sinéad O'Connor - 'Nothing Compares 2 U'

The Greatest Cover Songs of All-time  5. Sinéad O'Connor - 'Nothing Compares 2 U'

Prince wrote "Nothing Compares 2 U" in 1984, gave it to side project band The Family. 1985: released as album track eight, Paul Peterson sang it beautifully, nobody noticed. The Family disbanded after one album. Five years later, Irish singer Sinéad O'Connor recorded it for her second album with stark production and raw vulnerability. January 1990: released with John Maybury's iconic video—Sinéad's face in extreme close-up against black background, the single tear at 2:40. #1 in seventeen countries, four weeks US #1, biggest-selling single of 1990 worldwide. MTV phenomenon. The tear was real—thinking about her abusive mother. Prince eventually tried to reclaim it, but too late. Garrett Fisher explores generosity, vulnerability, and how Sinéad made Prince's song eternal.

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Kalaroga Shark Media. We're at number five on our countdown

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of the top ten best cover songs of all time,

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as voted by the staff at Kalaroga Shark Media. We've

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crossed the halfway point, and as we climb higher on

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the countdown, the stories get bigger, the cultural impact gets deeper,

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and the transformations get more profound. This week, we're looking

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at a cover that's inseparable from one of the most

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powerful music videos ever made. A cover that took a

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song by one of the greatest artists of all time

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and somehow made it more famous than he ever did.

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Nothing Compares to You by Shane O'Connor, That voice, that face,

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that single tear running down her cheek, the video that

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made you stop whatever you were doing and just watch

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the song that became the sound of heartbreak in nineteen ninety,

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but before Shane O'Connor made Nothing Compares to You one

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of the biggest hits of the decade. It was a

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deep album cut by a side project band that almost

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nobody had heard of, and the person who wrote it,

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the person who gave it away, was Prince. This is

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the story of how one of Prince's most Beautiful Songs

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sat unknown for five years until an Irish singer with

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a shaved head and an uncompromising vision turned it into

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a phenomenon. Let's Start. In nineteen eighty four, Prince was

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at the absolute peak of his powers. Purple Rain had

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just been released. The album would go on to sell

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over twenty five million copies worldwide. The film was a

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cultural event. Prince was everywhere MTV radio, stadium's magazines. He

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was arguably the biggest star in the world, and he

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was writing constantly, not just for himself but for other artists.

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Prince had this incredible generosity or maybe it was restlessness

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or abundance or all three three, where he'd write songs

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and then give them away to other artists. Sometimes these

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were songs he thought would work better for someone else's

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voice or style. Sometimes they were just songs he'd written

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and moved on from because he was already onto the

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next thing. In nineteen eighty four, Prince wrote a song

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called Nothing Compares to You. The story goes that he

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wrote it after a relationship ended with one of his

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longtime collaborators, Susan Moonsey, who was part of a girl

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group called Apollonia six that Prince had created. The song

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was deeply personal, achingly vulnerable. It was about the kind

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of heartbreak where nothing, not flowers, not being alone, not

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spending time with friends, can fill the void left by

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losing someone you love. Prince recorded a version himself, but

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he didn't release it. Instead, he gave it to a

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band called The Family. The Family was one of Prince's

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side projects. He was constantly creating these satellite acts bands

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that he would write for, produce, sometimes play on anonymously.

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The Family consisted of Paul Peterson on vocals, along with

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Susanna Melvoyn, Jellybean Johnson, and Eric Leads. They were talented musicians,

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part of the extended Minneapolis scene that revolved around Prince

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and Paisley Park. In nineteen eighty five, the Family released

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their self titled album on Paisley Park Records. Nothing Compares

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to You was track eight. Paul Peterson sang it beautifully,

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a smooth, soulful vocal over a sparse arrangement with synthesizers,

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program drums, and that distinctive mid eighties production that Prince perfected.

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The album came out. The single from it was the

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Screams of Passion, which got some attention, but Nothing Compares

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to You was just an album track. It wasn't promoted,

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it wasn't released as a single, Very few people heard it.

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The family disbanded after one album. Paul Peterson went on

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to work with other artists. The album became a footnote

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in Prince's vast catalog of productions, and Nothing Compares to

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You remained unknown to most of the world. That could

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have been the end of the story. Prince wrote a

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beautiful song, gave it to a side project band. The

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band released it, nobody noticed. Everyone moved on. But five

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years later, an Irish singer named Shanai O'Connor was working

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on her second album. SHANEI had released her debut album,

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The Lion and the Cobra in nineteen eighty seven. It

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had gotten critical acclaim and modest commercial success. She was

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known for her shaved head, her uncompromising artistic vision, and

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a voice that could shift from whispersoft vulnerability to primal

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scream intensity. She wasn't a typical pop star. She was confrontational, political,

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deeply spiritual, and utterly unwilling to compromise her vision for

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commercial success. For her second album, I Do Not Want

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What I haven't got. Shaney was looking for material she

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on its songs that matched the emotional honesty she was

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bringing to her own writing. Her manager suggested Nothing Compares

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to You. She listened to the Family's version, and she

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knew immediately that she had to record it. Shine's version

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of Nothing Compares to You was recorded with producer Nellie

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Hooper and Chris Barquette. The arrangement was completely different from

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the Family's version. It started with a simple program drum beat,

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that distinctive opening pattern that's now instantly recognizable, then keyboards.

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There was no attempt to smooth out her vocal, no

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attempt to make it pretty in a conventional sense. Shine

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sang with total vulnerability. Her voice cracked in places. She

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let the emotion overwhelm the technique. When she sang about

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how nothing compares to the person she lost, you believed

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every word, You felt it in your chest. The production

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was sparse. There were no big instrumental flourishes, no attempt

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to build to some massive climax. The song song just

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existed in this space of raw heartbreak, and Shanai's voice

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carried all of it. Nothing Compares to You was released

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as a single in January nineteen ninety, and then the

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music video came out. The video was directed by John Maybury.

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It's one of the simplest, most powerful music videos ever made.

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Shane's face in extreme close up against a black background.

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That's it. No narrative, no special effects, no cuts to

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other scenes, just her face, singing directly to the camera

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for the entire song. You watch her eyes, you watch

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the emotions cross her face, and about two minutes and

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forty seconds into the video, a single tear rolls down

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her left cheek. That tear became one of the most

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iconic moments in music video history because you couldn't tell

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if it was performance or if Shane was actually crying.

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It felt real. It felt like you were witnessing genuine heartbreak,

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not someone acting heartbroken. Years later, Shane revealed that the

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tear was real, but it wasn't about romantic heartbreak. She

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was thinking about her mother, who had died when Shine

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was young, who had abused her, and about the complicated

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grief of losing someone you loved but who also hurt you.

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But viewers didn't know that. They just saw someone breaking

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down on camera, being completely vulnerable, showing you what it

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actually looks like when you're trying to hold it together

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and you can't quite manage it. MTV played the video constantly.

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Vh one played it constantly. It was unavoidable, and every

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time it played, people stopped what they were doing and watched.

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The song went to number one in seventeen countries. In

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the United States, it topped the Billboard Hot one hundred

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for four consecutive weeks. In the UK, it stayed at

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number one for four weeks. In Canada, New Zealand, Australia,

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across Europe, everywhere it was number one. It became the

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biggest selling single of nineteen ninety worldwide. It won a

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Grammy nomination for Record of the Year. It was certified

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platinum multiple times over. It made Shanee O'Connor a global superstar,

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and almost nobody knew it was a cover. Almost nobody

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knew Prince had written it five years earlier for a

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band that had broken up after one album. We'll be

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right back. So what makes Shane's version so much more

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successful than the families? Why did this song sit unknown

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for five years and then suddenly become one of the

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biggest hits of the decade. Part of it is the

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vocal performance. Paul Peterson sang it beautifully, but he sang

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it as a soul ballad, smooth, controlled, polished. Shane sang

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it like someone who was barely holding herself together. The

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vulnerability in her voice was almost uncomfortable to listen to.

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It felt too raw, too exposed, and that rawn has

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made it impossible to ignore. Part of it is the production.

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The Family's version had that mid eighties synthesizer production that

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was already starting to sound dated by nineteen ninety. Shane's

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version had a starker, more timeless production that let the

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vocal take center stage. But the biggest part of it

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is the video. That close up of Shaneai's face, that tear.

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That's what made the song a phenomenon. MTV was at

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its peak in nineteen ninety. Videos could make or break careers,

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and this video was unlike anything else on the channel.

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Most music videos in nineteen ninety were narratives, performances, heavily

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choreographed productions. Shanei's video was just her face, and somehow

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that simplicity made it more powerful than anything with elaborate

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sets or special effects. You couldn't look away, and because

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you couldn't look away. You heard every word she was singing,

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You felt every emotion. The song in the video became inseparable.

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Prince's response to Shane's success with his song was complicated. Initially,

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he was pleased she'd taken something he'd written and made

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it huge. She'd honored the song. The royalties from it

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were substantial. As the songwriter, he was making money every

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time it was played, purchased, performed. But Prince also had

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mixed feelings about someone else having the definitive version of

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his song. He was competitive, he was a perfectionist. He

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eventually recorded his own version, performed it in concert, tried

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to reclaim it, but it was too late. Nothing compares

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to You belonged to Shane Now. When people thought of

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the song, they thought of her face, her voice, that tear.

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Prince's version, the one he eventually released, was received as

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Prince covering Shanee O'Connor, even though he'd written it. That's

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the power of a truly transformative cover. It doesn't matter

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who wrote it. It does doesn't matter who recorded it first.

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What matters is who made it unforgettable. Shinai O'Connor's career

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was never the same After Nothing Compares to You, she

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became one of the most famous musicians in the world.

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Her second album went multi platinum. She was on magazine covers,

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winning awards, selling out arenas, but fame made her deeply uncomfortable.

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She was outspoken about the Catholic Church, about child abuse,

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about Ireland's treatment of women. In nineteen ninety two, she

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tore up a picture of Pope John Paul the Second

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on Saturday Night Live, ending her mainstream career in America

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essentially overnight. She continued making music, speaking out on issues

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she cared about, refusing to compromise even when it cost

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her commercially. She had a complicated relationship with Nothing Compares

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to You. It was the song that made her famous,

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but it was also a reminder of a moment when

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the world paid attention to her voice before deciding it

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didn't like what she had to say. Shine O'Connor passed

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away in July twenty twenty three, at age fifty six.

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The tributes that poured in all mentioned Nothing Compares to You.

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The video was played millions of times. People who'd seen

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it when it first came out in nineteen ninety watched

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it again and cried. The song became her eulogy, her legacy,

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the thing people would remember forever, and Prince, who'd written

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it in nineteen eighty four and given it away, who'd

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watched it, become huge for someone else who tried to

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reclaim it. Prince passed away in twenty sixteen. His catalog

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of work is astonishing, hundreds of songs, dozens of albums,

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innovations in music and performance that changed popular culture. But

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Nothing Compares to You remains one of his most famous compositions,

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not because of his version, because of Shinai's That's why

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Nothing Compares to You is number five on our countdown

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because it's a perfect example of a great songwriter being

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generous enough to give away a master piece, Because it

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shows that sometimes the person who writes a song isn't

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the person who can best communicate its emotional truth. Because

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that music video is one of the most powerful four

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minutes ever put on television, and because Shanai O'Connor took

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a song about romantic heartbreak and made it about every

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kind of loss, every kind of grief, every moment when

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you realize that nothing, absolutely nothing can fill the space

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left by someone who's gone Prince wrote a beautiful song.

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Shanee O'Connor made it eternal. This is Garrett Fisher and

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this is the hit Maker Chronicles. Join us next Sunday

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for number four on our countdown of the top ten

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best cover songs of all time.