 " 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 . 
