"From the Bottom of My Broken Heart" is a song by American singer Britney Spears from her debut studio album, ...Baby One More Time (1999). It was released on December 14, 1999, by Jive Records as the fifth and final single from the album. After Spears recorded an unused song from Toni Braxton and sent it through Larry Rudolph to several labels, executives from Jive Records commented that it was very rare to hear someone so young who could deliver emotional content and commercial appeal, appointing the singer to work with producer Eric Foster White. The teen pop ballad was written and produced by White, and features Spears singing about the loss of a first love and how breaking up can be hard.
"From the Bottom of My Broken Heart" received mixed to positive reviews from music critics, who noted the song as a classic hit and competent single, despite considering it unremarkable like other ballads on the album and calling it "another rejection ballad that refers to kissing but nothing else". "From the Bottom of My Broken Heart" achieved moderate success, peaking at number 37 in Australia, and 23 in New Zealand. In the United States, "From the Bottom of My Broken Heart" reached number 14 on the Billboard Hot 100, and 17 on Pop Songs, being later certified Platinum by the Recording Industry Association of America (RIAA) on March 28, 2000, for shipping 1,000,000 physical units of the single. It was the 8th best-selling physical single of the 2000s in the country.
An accompanying music video, directed by Gregory Dark from November 22–23, 1999, was released on December 17, 1999. It portrayed Spears packing her belongings as she readies herself to move away from home, and feeling upset because she knows that she is going to miss her first love. The video was the subject of controversy among the press, who panned the singer for hiring an adult filmmaker to direct her video. A Spears representative commented that they were only aware of Dark doing music videos. The singer performed "From the Bottom of My Broken Heart" in a few live appearances, including at the 42nd Annual Grammy Awards, in a medley with "...Baby One More Time", and in three of her concert tours.
Background
In June 1997, Spears was in talks with manager Lou Pearlman to join female pop group Innosense. Her mother Lynne asked family friend and entertainment lawyer Larry Rudolph for his opinion and submitted a tape of Spears singing over a Whitney Houston karaoke song along with some pictures. Rudolph decided he wanted to pitch her to record labels, therefore she needed a professional demo. He sent Spears an unused song from Toni Braxton; she rehearsed for a week and recorded her vocals in a studio with a sound engineer. Spears traveled to New York with the demo and met with executives from four labels, returning to Kentwood the same day. Three of the labels rejected her, arguing audiences wanted pop bands such as the Backstreet Boys and the Spice Girls, and "there wasn't going to be another Madonna, another Debbie Gibson, or another Tiffany." Two weeks later, executives from JIVE Records returned calls to Rudolph. Senior vice president of A&R Jeff Fenster stated about Spears's audition that "It's very rare to hear someone that age who can deliver emotional content and commercial appeal. [...] For any artist, the motivation—the 'eye of the tiger'— is extremely important. And Britney had that." They appointed her to work with producer Eric Foster White for a month, who reportedly shaped her voice from "lower and less poppy" delivery to "distinctively, unmistakably Britney." After hearing the recorded material, president Clive Calder ordered a full album. "From the Bottom of My Broken Heart" was written by Eric Foster White, for Spears' debut studio album, ...Baby One More Time (1999). Spears recorded the vocals for the song in 1997 at 4MW East Studios in New Jersey and at Battery Studios in New York City, New York. Dan Petty played the guitar, while the bass guitar was done by Andy Hess. The song was later mixed by White and Chris Trevett, while background vocals were provided by Spears, Angie Simmons, Don Philip and Andrew Fromm. It was released on December 15, 1999, as the final single from ...Baby One More Time.