"From the Bottom of My Broken Heart" was released on December 15, 1999, as the final single. The song also received mixed reviews, finding the song a classic hit and competent single, despite considering it as an unremarkable song that refers only to kissing. "From the Bottom of My Broken Heart" achieved moderate success, peaking at number thirty-seven in Australia, and twenty-three in New Zealand. Through imports, the song reached one hundred seventy-four in the United Kingdom. In the United States, "From the Bottom of My Broken Heart" reached number fourteen on "Billboard" Hot 100, and seventeen on Pop Songs, and was later 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. The music video, directed by Gregory Dark, was released on December 17, 1999. It was highly criticized due to the fact that Dark had previously directed porn films.