Out of all the music videos made off of Britney Spears’ debut album, “From the Bottom of My Broken Heart” is easily the least celebrated. While the tune is catchy and the pop star’s wardrobe and hair are most definitely on point (that bucket hat, amirite?), with no inimitable dance routine at its core nor MTV “Making the Video” special documenting the behind-the-scenes goings-on to accompany it, the segment largely flew under the radar (though Glamour magazine did rank it as her 13th best video overall in 2016).
Lensed in November 1999 and released the following month, the shoot was directed by Gregory Dark, who is described in a 2000 Entertainment Weekly blurb as “the former porn auteur of ‘New Wave Hookers’ fame.” Quite an unlikely candidate to helm a video for the teen starlet, especially considering the fact that, as Dark told EW, at the time Britney’s label, Jive Records, was hoping to “re-image her a bit” following her sexy schoolgirl turn in 1998’s “ . . . Baby One More Time.”
Chronicling a first break-up, “From the Bottom of My Broken Heart” features a ringlet-crowned Spears swaying on a tire swing, waiting at a dusty roadside bus stop and laying in a field of sunflowers while mournfully singing lyrics like “Loneliness up ahead, emptiness behind – where do I go?” and “You were my first love, you were my true love, from the first kisses to the very last rose.”
Further cementing her image as a small-town girl at heart, the video also sees the singer packing up her belongings and moving away from her childhood home, saying goodbye to her mom, sister and boyfriend on the wraparound front porch of a picturesque Victorian residence. Purported to be in the fictional rural town of Cedar Springs, in truth the idyllic dwelling can be found about 15 miles northeast of Los Angeles at 240 W. Hillcrest Blvd. in Monrovia. (Please remember this is a private home. Do not trespass or bother the residents or the property in any way.)