Don McLean's Eight-Minute, 36-Second Gamble

Don McLean's Eight-Minute, 36-Second Gamble

Don McLean recorded an eight-minute, thirty-six-second song on May 26 in New York, a gamble that became the longest track ever to top the American chart.

Key points

  • Don McLean was born in New Rochelle, New York, in 1945, and childhood asthma left him long hours that he filled with music.
  • McLean's first album, Tapestry, was rejected by seventy-two labels before the tiny Mediarts took a chance on it.
  • The song ran eight minutes and thirty-six seconds, sat at the top of the American chart for four weeks, and held the record for longest chart-topper for nearly half a century.
  • The original working manuscript of the song sold at auction in New York for more than one million dollars.

· Published · 4 min read

AI-generated illustration: a wall of speakers
AI-generated illustration

The studio tape rolled on the morning of May 26 in New York, and Don McLean, a lanky singer with asthma and a folk guitarist's scruff, began laying down a song that would eat up most of a side of vinyl. He was nearly twenty-six, he had already been rejected by an absurd number of labels, and he was about to stake everything on a rambling, riddle-wrapped requiem for a rock-and-roll star he had never met.

Asthma, Abruzzo and The Weavers

McLean was born in New Rochelle, New York, in 1945, the son of a father of Scottish stock and an Italian-American mother from Abruzzo. Childhood asthma kept him out of school so often that he had long hours to fill, and he filled them with music. The record that rearranged his brain was a live album by The Weavers, the close-harmony folk group, captured at Carnegie Hall in 1955. That record turned a lonely kid into a folk obsessive.

The other event that shaped him arrived four years later, when a small plane went down in a frozen Iowa field and took Buddy Holly with it. McLean was just entering his teens, but the newspaper headlines about the crash lodged in him like a splinter. Much later, they would surface inside a song about loss, change, and the end of a certain kind of American innocence.

Seventy-two rejections and Mediarts

By the time McLean recorded his first album, Tapestry, in the late sixties, he had played the folk-club circuit from Greenwich Village to Washington, D.C., and had even learned stagecraft from the folk patriarch Pete Seeger. But Tapestry could not find a home. One label after another turned it down — seventy-two of them, a number that would sound like a punchline if it had not nearly broken him. Finally a tiny outfit called Mediarts took a chance.

The break was not the record itself but the paperwork. When a larger company, United Artists, absorbed Mediarts, McLean suddenly had real promotion behind his second album. Its lead single had been hanging around unfinished until he wove together the Holly tragedy, a vision of a nation shedding its old skin, and a cryptic cast of characters that fans would spend decades decoding.

Eight minutes thirty-six seconds

Radio programmers were terrified of it. The song ran eight minutes and thirty-six seconds, an eternity for pop radio in the early seventies, and DJs preferred bites of three minutes. But listeners would not stop calling to request it. By mid-January of the following year it sat at the very top of the American chart and stayed there for four weeks. It was the longest song ever to rule that chart — a record it kept for nearly half a century, until Taylor Swift finally edged past it in a different era.

It was the longest song ever to rule that chart — a record it kept for nearly half a century, until Taylor Swift finally edged past it in a different era.

McLean himself refused to explain what it all meant. A Chicago disc jockey had already printed his own interpretation within days of the song's release, but the singer kept quiet for years, which only deepened the game. Much later he admitted the lyric was partly autobiography, an abstract map of his own life from the mid-fifties through the end of the sixties, with Buddy Holly as the ghost at the center of the myth.

The gamble paid for itself many times over. Decades later, the original working manuscript of the song sold at auction in New York for more than one million dollars. And the album produced a second hit that showed another side of McLean: a quiet tribute to the painter Vincent van Gogh, inspired by a book and by the swirl of The Starry Night, that climbed to the top of the British chart. A folk singer who had been rejected seventy-two times had become, for a while, the biggest voice in the world.

The mystery of the song outlasted the hits. In the early eighties McLean was still touring, often asked to play the one song he had grown tired of, and he kept doing it because the audience demanded the riddle again. The boy who once delivered newspapers in a small city north of New York had written a kind of national mirror, and no one — not even him — could quite explain what was reflected in it.

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