"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).

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.

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.

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."

[2] 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.

"[3] 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.

The song was later mixed by White and Chris Trevett, while background vocals were provided by Spears, Angie Simmons, Don Philip and Andrew Fromm.

[11][12] Chuck Taylor of Billboard noted that the singer "turn toward the sad side" on the track, with its lyrics talking about the loss of a first love and how breaking up can be hard.

[18] Caryn Ganz of Rolling Stone called "From the Bottom of My Broken Heart" a "further hit" from ...Baby One More Time, along with "Sometimes" and "(You Drive Me) Crazy".

[21] Billboard critic Chuck Taylor praised the song, and did a further review on his column: "'From the Bottom of My Broken Heart' possesses a breezy air that is certain to continue her breakneck success on the singles charts.

Eric Foster White is at the helm this time, writing and producing a song that will easily appeal to Miss Spears' young core, with the potential to chart the more mature AC audience, too.

[8]Also from Billboard, Chuck Arnold wrote that "there’s just not enough depth or texture to her voice, but the little quiver in her chirp does serve her well on the final single from the album, a weepie one about losing your first love".

[24] Nicholas Hautman, from Us Weekly, was more positive and opined that "this teenybopper torch song is no 'Sometimes', but it’s a classic in Spears’ catalog that some fans unfairly push to the side".

[28] On March 28, 2000, "From the Bottom of My Broken Heart" was certified platinum by the Recording Industry Association of America (RIAA), for shipping 1,000,000 physical units of the single in the country.

According to Dark, the label hired him with the intention of re-image Spears from the naughty schoolgirl persona of "...Baby One More Time", and stated that they "wanted a much more story-oriented video without dance, one that was serious and emotional.

[36][37] The music video portrays Spears packing up 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.

[38] According to writer Linda Ruth Williams, the music video attracted attention from the press because of "the clash between Spears' wholesome image and Dark's unwholesome back catalogue.

"[35] Lucy O'Brien, author of She Bop II: The Definitive History of Women in Rock, Pop and Soul, noted that hiring Dark as the video director implied that Spears was not that innocent.

[38] Bemis commented, however, that Spears already had "a history of questionable decisions", and cited her Rolling Stone photoshoot done in early 1999, which was condemned by the American Family Association, as an example.

While a TV tabloid recently reported that an old bayou beau in Louisiana has mother Spears’ approval, fantasizing fans want to believe Britney's dallying with that braided moppet from N’Sync or a member of the Backstreet Boys.

After singing a shortened version of the song, she then took a few moments to shuffle into a form-fitting red rhinestone outfit (with side cutouts) and emerged onto a stage to perform "...Baby One More Time.