On March 26 1986, Live To Tell was released as a single in North America by Sire Records. 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. It was also a significant Adult Contemporary crossover success, becoming her first single to reach number-one on Billboard’s Hot AC chart where it reigned for three weeks.
Today In Madonna History 
I have a lot of memories associated with this song. MTV heavily promoted the world premiere of the video, and my older brother and I sat in front of the TV waiting for it to air. After it did, we were so surprised by her toned-down, simple look. I don’t remember ever seeing the Sean Penn movie associated with the video–maybe we did, maybe we didn’t. The song and video are what’s memorable. The next day at school (I was in the 7th grade) there was a lot of buzz about the video and song. One of my classmates in art class had cut out a picture from the video from a teen magazine and was drawing her for his art project. Later, my family went to my grandparents’ house (for Easter dinner, I think) and my grandmother had purchased the 45 record for her record player. I couldn’t believe my grandmother, of all people, bought a Madonna record. She told me that she interpreted the lyrics to be her (Madonna) apologizing for the nude photos in Playboy, saying she “learned her lesson well,” and was asking for forgiveness. LOL I begged her to give me the record, and she finally did. I was so proud riding in the back seat of my parents station wagon, holding that record in my lap. I just stared at the photo of Madonna on the record sleeve all the way home, and was absolutely mesmerized by her.
Bravery, determination and battered hope-that’s Live to Tell! Live to Tell is Madonna at her absolute best and my favorite song of all time! Not only that, it’s Rock’s best song ever!
Live to tell was a milestone achievement. The record stands up today and was and still remains a timeless beauty I remember hearing it for the first time and seeing the video. Every time you hear live to tell it’s as good as the first time. Outstanding
When it comes to laying down the vocal track, Madonna is legendary for nailing it in one take — a prime example of her preternatural instinct for how to pack an emotional wallop into a pop song within her admittedly limited vocal range, which is what makes her one of the greatest — and most under-rated — songwriters in pop music history.
I wish she’d release these old singles on streaming apps! They’ve released 1989 through 2000, but still many remixes to go! I’m just glad they nevee remixed this song into a dance song like they do now with ballads. Keep the singles coming Madge!