Don McLean - "American Pie" - 1971. 8 minutes, 37 seconds
Modern technology has allowed singles to get longer, but the OG of this list didn't have the luxury of digital music formats. When "American Pie" was released in 1971, it took up both sides of a 45 RPM record, meaning you'd have to flip the record over to hear the whole song. Even so, "American Pie" not only charted, but it reached number one. It held the title of longest song to reach number one for fifty years, until being dethroned by Taylor Swift.
"American Pie" is so thick with metaphor that its true meaning is open to debate and interpretation. All we really know for sure is that "the day the music died" refers to the 1959 plane crash that killed Buddy Holly, Richie Valens, and The Big Bopper. The most popular interpretation is that the rest of the song is a homage to sixties music, with references to Elvis, Bob Dylan, Joan Baez, The Beatles, and Janis Joplin.
Though McLean stubbornly refuses to clarify or confirm what the song is about, he has poked holes in this interpretation, saying the song is more about the general tumult of the sixties, for instance, the "marching band" that "refused to yield" was not The Beatles, but the military-industrial complex, and that their "sweet perfume..." is tear gas.
In 2015 the original manuscript was sold at auction, further shedding light on the song's meaning. The sale catalogue noted that in McLean's words "in 'American Pie' things are heading in the wrong direction. [Life] is becoming less idyllic" It would be hard for a modern audience to relate to a song about how great music was sixty years ago, but as another generation contends with its own "interesting times", the vague notion that things are getting worse, precipitated by a traumatic event in the recent past that affected us all is very relatable.