Turns out, there’s quite a story behind Madonna’s subversive cover of this iconic American pop song

Since its release in 1971, Don McLean’s epic, eight-and-a-half-minute song “American Pie” has become an enduring part of American culture. It’s sold millions of copies, been covered by multiple different artists, and was even the subject of a 2022 Paramount+ documentary called The Day the Music Died: The Story of Don McLean’s American Pie. (It also held the record for being the longest song to reach No. 1 for almost 50 years before Taylor Swift’s “All Too Well (10 Minute Version)” broke the record in 2021.)

In 2000, the Queen of Pop herself, Madonna, recorded her own version of the song to promote the soundtrack to her movie The Next Best Thing, co-starring Rupert Everett.

The film is about a single yoga instructor named Abbie (Madonna), who decides to raise a child with her gay best friend, Robert (Everett). When their friendship falls apart, a bitter custody battle ensues. And in the end, nobody is happy.

Despite opening at #2 at the box office, The Next Best Thing was panned by critics and ultimately failed to earn back its $25 million budget. Everett later said it was responsible for killing both his acting career and his friendship with Madonna, who he had been close with prior to filming.

“We don’t see each other anymore,” he told The Telegraph’s Stellar Magazine in 2020, adding that she’s “an amazing person and that part of my life was incredibly exciting. To be doing a film with her, and to be a friend of hers, and to have been such a fan of hers. But the fallout from the movie’s failure was gigantic for me, like an outer-space explosion.”

Perhaps the only positive thing to come out of the ill-fated project was its soundtrack, which Madonna executive produced. She handpicked all 12 songs, contributing two of her own: an original ballad called “Time Stood Still” and an electronic version of McLean’s 1971 hit, which Everett reportedly convinced her to record.

Co-produced by Madonna and William Orbit, the cover is an abridged version of McLean’s original track and features backing vocals by Everett, who also appears in the music video.

While promoting the single, Madonna said, “To me, it’s a real millennium song. We’re going through a big change in terms of the way we view pop culture because of the internet. In a way, it’s like saying goodbye to music as we knew it. And to pop culture as we knew it.”

The music video was directed by Philipp Stölzl and features a range of everyday Americans, including queer people and couples. At one point, two women kiss. But because it was the year 2000, when both DOMA and DADT were still in effect and nearly half of U.S. states still had statutes criminalizing gay sex, MTV refused to air it.

So, a second version was cut featuring a dance remix of the song and omitting the sapphic moment. It was a rare moment in Madonna’s boundary-pushing career that she gave in to censors.

Sort of.

Three years later, she would give a belated middle finger to the MTV execs who censored her by locking lips with Britney Spears at the 2003 MTV VMAs, a pop culture moment that since has become almost as iconic as McLean’s original song.

Upon its release, “American Pie” peaked at No. 1 in several different countries. (Curiously, the single wasn’t actually released in the United States, but it still managed to reach No. 29 on the Billboard Hot 100.) It was also included as a bonus track on the international edition of her eighth studio album Music.

Despite being a worldwide hit and selling over 1 million copies, “American Pie” wasn’t featured on Madonna’s 2001 greatest hits compilation album GHV2. At the time, she said regretted including it as a bonus track on Music, so she was “punishing” it.

“It was something a certain record company executive twisted my arm into doing, but it didn’t belong on the album so now it’s being punished,” she told the BBC in an interview. “My gut told me not to, but I did it and then I regretted it so just for that reason it didn’t deserve a place on GHV2.”

The song also wasn’t featured on her 2009 greatest hits compilation album Celebration, although the music video was included on the DVD Celebration: The Video Collection.

By 2022, however, Madonna seemed to have warmed up to it… At least enough to include a remixed version was included on her Finally Enough Love 50 Number Ones album, although she didn’t perform it on her most recent Celebration Tour.

When asked what he thought of the Queen of Pop’s cover of his signature song, McLean told UK Music Reviews in 2021, “Well, you really couldn’t ask for a better present anywhere in the world than to have Madonna do what she did with that song.”

He continued, “She put it out two different ways; she had it played on three different times in the movie that she made. So, for me, it was just this enormous gift from this humongous star.”