Both artists were supporting their debut albums when they performed on the Grammys stage in 1989
Annie Lennox remembered O'Connor with a moving cover of her hit cover "Nothing Compares 2 U" during the in memoriam segment of the awards ceremony, which honored those in the music industry who died in 2023.
Performing towards the beginning of the show, Chapman joined country singer Luke Combs on stage for a rendition of her hit "Fast Car." Combs, 33, helped bring the song and Chapman back into the spotlight when he released a cover of the song in 2023, over 35 years after its initial release.
Combs' cover of the song was nominated for a Grammy in 2024 in the best country solo performance category. The single also reached the No. 1 spot on the country charts, as well as No. 2 on the Billboard Hot 100. "Fast Car" was named song of the year for Chapman and single of the year for Combs at the CMA Awards in November 2023.
On Feb. 22, 1989, Chapman first graced the Grammys stage to perform the song, which was released in April 1988 on her self-titled debut album.
That night, the singer was nominated for six Grammy awards and took home three: best contemporary folk recording, best pop vocal performance (female) and the coveted best new artist gramophone. The album also features her hit song "Talkin' 'bout a Revolution."
She has been nominated for 13 Grammys throughout her career and won four.
A young Chapman performed solo on the Grammys stage in 1989 with her guitar and a simple spotlight for accompaniment. She wore a black shirt in both performances, though her hair was cropped short during the song's Grammys debut. Chapman received a standing ovation after both performances.
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O'Connor and her debut album The Lion and The Cobra were nominated for one Grammy in 1989 in the category for best rock vocal performance, female. She didn't win the award that night, but she did perform the album's second single that night, "Mandinka," which had originally been released in December of 1987.
The then 21-year-old Irish singer performed her dance hit in a simple black crop top and ripped jeans, wearing the shaven hairstyle she'd become known for. It was about a year before her cover of Prince's "Nothing Compares 2 U" would top music charts around the world.
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