Critical Response
"Live to Tell" was generally well received by music critics. In a review of the album True Blue, Stephen Thomas Erlewine from Allmusic called it a "tremendous ballad that rewrites the rules of adult contemporary crossover". Jim Farber from Entertainment Weekly called the song "her best ballad to date". In a review of her compilation album The Immaculate Collection, David Browne from the same magazine called it "one of her few successful shots at being a balladeer". Blender's Tony Power said that the song "is her first ballad not sunk by her ordinary pipes". Alfred Soto from Stylus Magazine felt that "the song's set of lyrics remain her best" and that the vocals "seethes with a lifetime's worth of hurts which she nevertheless refuses to share". Sal Cinquemani from Slant Magazine called the song "striking" adding that it "rewrote the rules of what a pop song was supposed to sound like".
Adam Sexton, author of Desperately Seeking Madonna: In Search Of The Meaning Of The World's Most Famous Woman, felt that "Live to Tell" made a provocative companion to "Papa Don't Preach", the second single from the album. He added that "Madonna appropriately measured the safety of silence against the urge to unburden herself." Sexton also complimented the production, saying that the "music itself suggests a threatened annihilation, a fact that makes it more haunting."
Allen Metz and Carol Benson, authors of The Madonna Companion: Two Decades of Commentary, felt that the track expanded Madonna's musical horizons. According to them "Live to Tell" was a compelling track which Madonna sang with moving conviction. J. Randy Taraborrelli, author of Madonna: An Intimate Biography, was pleased with the track, denoting it as a vehicle of growth for Madonna. Erica Wexler from Spin, while reviewing True Blue, called "Live to Tell" as "dark and moody, dense with dramatic mystery. In this mushy tale of lost innocence, Madonna very theatrically conveys a lost fatalism. Her fragile voice aches for reassurance and healing when she sings 'Will it grow cold? The secret that I hide, Will I grow old?"
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