"From the Bottom of My Broken Heart" is a song by American recording artist Britney Spears. The song was written and produced by Eric Foster White for Spears' debut studio album, ...Baby One More Time (1999). The song was released on December 15, 1999 by Jive Records, as the fifth and final single from the album. The sentimental teen pop ballad, speaks of a woman recalling her first love and wishing it had not ended, as her true emotions are revealed "from the bottom of [her] broken heart."
"From the Bottom of My Broken Heart" received mixed reviews from music critics, with some calling it a hit and competent as a single, but unremarkable as a song that only refers to kissing and nothing else. The song achieved moderate success, peaking at number fourteen in the United States' Hot 100, and inside the top-forty in Australia and New Zealand. The song was certified Platinum by the Recording Industry Association of America (RIAA) on March 28, 2000, for selling over 1,000,000 physical units of the single.
An accompanying music video, directed by Gregory Dark, was released on December 17, 1999. It portrayed Spears packing her belongings as she readies herself to move away from home. She is upset because she knows that she is going to miss her first love. At the time it was released, it was noted the music video sets Spears on the fast track to adulthood. Spears performed the song at the 42nd Grammy Awards as a medley, along with "...Baby One More Time", and on three tours, ...Baby One More Time Tour, Crazy 2k Tour and Oops!... I Did It Again World Tour.