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The ballad was written by Diane Warren. Reid was able to convince the singer to record it and include on her album. Lyrically, the song alludes to a “blistering heartbreak” in which Braxton begs a former lover to return and undo the pain he has caused. It won a Grammy Award for Best Female Pop Vocal Performance at the 39th Annual Grammy Awards in 1997.
Un-Break My Heart” attained commercial success worldwide. In the United States, the song reached number one on the Billboard Hot 100, where it stayed a total of eleven weeks, while reaching the same position on the Hot Dance Club Songs and Adult Contemporary component charts.
When Billboard celebrated their 40 years charting from 1958 to 1998, the song was declared as the most successful song by a solo artist in the Billboard Hot 100 history. Bille Woodruff directed the accompanying video for the single. It portrays Braxton mourning the death of her lover, while remembering the good times they had together.
Braxton performed the song on the opening ceremony of the 1996 Billboard Music Awards. Un-Break My Heart” has been covered by several artists, including American alternative rock band Weezer on the album Death to False Metal. Diane Warren wrote “Un-Break My Heart” in 1995. When asked about her songwriting process, she said that songs usually come to her from a title, a chorus, or a drum beat.
Un-Break My Heart” was conceived from its title, and, according to Warren, “it popped into my head, and I thought, ‘I don’t think I’ve heard that before, that’s kind of interesting. I started playing around on the piano with these chords and did a key change, and then I knew, ‘OK, this is magic. Warren further explained that she wrote “Un-Break My Heart” as a ballad and dance song, because that was the way she heard it.
When Warren played the finished song to Arista Records’ president L. Reid, he thought it would fit Braxton’s then upcoming album. When “Un-Break My Heart” was sent to Braxton, she expressed dislike for the song. According to Warren, “Toni hated the song.