On May 31 1986, Madonna’s Live To Tell hit #1 for 3 weeks on US Hot Adult Contemporary singles chart.

The haunting and dramatic ballad, written and produced by Madonna & Patrick Leonard, was the first commercially released collaboration between the pair – a songwriting partnership that is viewed by many fans as one of her most creatively successful.

Leonard had previously been involved with Madonna’s Virgin Tour as musical director, and when Madonna agreed to participate in Live Aid in the Summer of 1985, she asked him to collaborate on a new song for the performance, which evolved into Love Makes The World Go Round.

Although both songs would find their way on to Madonna’s next studio album, True Blue, at the time of Live To Tell’s release the album’s title had not yet been decided. Instead, the song was used to promote Sean Penn’s film At Close Range, in which it was featured alongside an original score composed by Leonard.

He had initially composed the music that evolved into Live To Tell for another film he had been invited to score for Paramount, titled Fire With Fire. The producers of the film passed on the theme. Leonard recalled the subsequent series of events that led to the song’s completion in The Billboard Book of Number One Hits by Random House:

“Madonna said ‘This song would be great for Sean’s new movie.’ She wrote the lyrics–she just wrote them on the spot, which is what we always do. I don’t think we’ve ever taken more than three hours to complete a song from start to finish. She sang it on the demo only once and left with the cassette. That day I went to work with Michael Jackson on some transcriptions for material he was writing for the Bad album. The phone rang at Michael’s and it was Sean. He said ‘I’m over at the director’s house and Madonna just brought the song over. We love it and we’d like to talk to you about it.’ … We recut the song, but we used the same vocal. She only sang it once for the demo and that was the vocal we used because it was so innocent and so shy. She had a legal pad in her hand and you can hear the paper. It’s as raw as raw can be and that’s part of what gave it all its charm.”

When the demo recording of Live To Tell eventually surfaced, it became evident that Madonna had in fact re-recorded the first verse, but all remaining vocals do indeed appear to have been carried over from the demo to the final mix (along with a generously added dose of reverb to smooth over the rough edges of the demo take).

Given the song’s dark undercurrents and unresolved narrative, it was a bold choice for a single release. It marked a dramatic shift from the yearning love song, Crazy For You – her only other ballad to have been issued as a single at the time. But any radio programmers who were hesitant to consider Madonna as a serious artist simply couldn’t deny the artistry of the song and nor could record buyers, with the combined support sending Live To Tell straight to the top of the pop charts.

Live To Tell was Madonna’s third #1 single on the Billboard Hot 100, and her #1 on the Adult Contemporary chart, where it would reign for three weeks.