On May 31, 1986, “Live To Tell” hit #1 for 3 weeks on US Hot Adult Contemporary singles chart.
The song was Madonna’s third number-one single on the Billboard Hot 100, and her first number-one on the Adult Contemporary chart.
In an interview about the song, Madonna said, “I thought about my relationship with my parents and the lying that went on. The song is about being strong, and questioning whether you can be that strong but ultimately surviving.”
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 Entertainment Weekly magazine called it “one of her few successful shots at being a balladeer”.
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”.
Edna Gundersen from USA Today called the song “a moody heart-tugger, may be her best song ever.”
On May 30, 2003, Callaway Editions announced that Madonna would make publishing history as her children’s book, “The English Roses” would be released simultaneously worldwide in 30 languages in 100 countries.
“The English Roses” is a children’s picture book written by Madonna and illustrated by Jeffrey Fulvimari, which later became a series of children’s books by both artists. The books are about the life of five schoolgirls in London and their problems.
On May 29, 1990, Toronto police threatened to arrest Madonna on the grounds of lewd and obscene behavior for the “Like A Virgin” masturbation sequence in her Blond Ambition concert. The show went on unaltered, and no charges were made after the tour manager gave the police an ultimatum: “Cancel the show, and you’ll have to tell 30,000 people why.”
Madonna performed 3 sold-out concerts at the SkyDome, in Toronto, Ontario, Canada.
On May 28, 2008, Madonna learned that she was officially going to be allowed to adopt David Banda. The High Court in Malawi granted Madonna permanent adoption of 2-year-old David Banda. Madonna’s lawyer said, “We are very happy with what the judge has ruled. Finally the court has granted Madonna full adoption rights of the boy…It’s all over, thank God. It is a positive and beautiful judgment that will have an impact on Malawi’s adoption laws.”
On May 27, 1985, Madonna appeared on the cover of Time Magazine. Photos by Francesco Scavullo.
On May 26, 1990, Madonna is honored with Pop Artist Of The Decade, Dance Artist Of The Decade and Dance Single Of The Decade (“Into The Groove”) in Billboard magazine’s “Music Of The 80s” Poll.
On May 25, 1990, Madonna cancels a third scheduled “Blond Ambition” concert at the Rosemont Horizon, Chicago, IL, due to laryngitis.
On May 24, 1988, “Madonna – Ciao Italia: Live From Italy” was released on home video and laserdisc.
The release featured a combination of footage from her shows in Turin, Italy (September 4 1987), the tour’s final date in Florence, Italy (September 6 1987), along with additional clips from an earlier show in Tokyo (June 22 1987). The full Turin concert had been previously broadcast in Europe, while the complete Tokyo performance was issued exclusively in Japan on VHS and laserdisc six months prior to the release of “Madonna – Ciao Italia: Live From Italy”.
On May 23, 1989, Madonna’s “Like A Prayer” album was certified double platinum (2 million copies).
On May 22, 1990, Madonna’s “I’m Breathless: Music From And Inspired By The Film Dick Tracy” album was released.
In the December 1994 issue of Q magazine, Madonna declared:
“I would have to say the favourite record that I’ve made is the soundtrack to Dick Tracy (“I’m Breathless”). I love every one of those songs… My judgement is never based on the world’s reaction.”