It may be difficult for most fans, but the singer herself managed to sum up her career in some of her most remembered songs – only one album repeats itself
Few artists have become as iconic as Madonna. A pop music icon, the singer built an immense catalog of hits throughout a career that began in the 1980s.
Amidst her extensive discography, it is difficult to single out the most iconic songs. However, the artist herself did this work in an interview.
During a story in the HuffPost (via Far Out Magazine), Madonna was asked to choose her five most iconic songs. Although the number is small compared to the amount of hits, she managed to make her choices aiming to contemplate some of the most important phases of her career.
Madonna’s five most iconic songs, according to her, are listed below. They were listed by the singer randomly, in no order of importance.
1) “Like a Virgin”
Title track and lead single from Madonna’s second album, “Like a Virgin” became one of his trademarks as soon as it was released in 1984, just a few days before the album itself. Composed by Tom Kelly and Billy Steinbergthe song addresses a new relationship started by the second mentioned, after a complicated period in his life.
At first, the producer didn’t like the song. Nile Rodgers (Chic). However, it pleased Madonna.
In an interview for Rolling Stone USA In 2009, she commented on her first impressions of “Like a Virgin” and “Material Girl”which were shown to Rodgers at the same time, still in their demo version.
I liked both of them because they were ironic and provocative at the same time, but they were also not like me. I’m not a materialistic person and I certainly wasn’t a virgin, and by the way, how can you be like a virgin? I liked the play on words, I thought it was clever. They’re so specific, so cool. I never realized they would become my trademarks.”
In addition to its radio success, “Like a Virgin” was marked by live performances. On the tour Blond Ambitionin 1990, Madonna debuted her famous look with the “cones” on her breasts, designed by the famous fashion designer Jean Paul Gaultier.
2) “Like a Prayer”
Like “Like a Virgin”, “Like a Prayer” angered the most conservative and religious people at the time of its release.
The title track from the 1989 album is full of religious elements – specifically Catholic – both in its lyrics and in its controversial music video. Madonna had a Catholic upbringing and spoke about it to Rolling Stone USA when the song was released.
Once you’re Catholic, you’re always Catholic – in terms of your feelings of guilt and remorse and whether or not you’ve sinned. Sometimes I’m wracked with guilt when I don’t need to be, and that, for me, is what’s left of my Catholic upbringing. Because in Catholicism you’re born a sinner and you’re a sinner all your life. No matter how much you try to run from it, sin is inside you all the time.”
The video for “Like a Prayer” has sparked controversy with religious groups and the Vatican itself for depicting burning crosses, a church and people who appear to be wearing Ku Klux Klan uniforms. The singer is also shown interacting with a black Catholic saint.
“Like a Prayer” was also used in a Pepsi commercial. Due to the religious controversy, the company canceled its contract with the singer, as well as its sponsorship of the tour. Blond Ambition. Madonna still received US$5 million as compensation for what happened.
3) “Express Yourself”
Madonna’s third choice was another song from the album Like a Prayer (1989): “Express Yourself”. Considered today a kind of feminist anthem for women’s rights and free sexuality, the song was the first songwriting partnership with the producer Stephen Bray. The two met when they were part of the group The Breakfast Club.
In the book Madonna ‘talking’: Madonna in Her Own Wordsthe artist comments on the lyrics of the song, which in itself is already quite clear. She explained (via Songfacts):
The ultimate thing behind this song is that if you don’t express yourself, if you don’t say what you want, then you’re not going to get it. And in effect you’re trapped by your inability to say what you feel or go after what you want.”
The track’s video, directed by filmmaker David Finchercost $5 million and was the most expensive ever made at the time. In the video, Madonna appears as a male figure, deliberately switching gender roles.
In 2011, Lady Gaga released the album and single “Born This Way” and was accused of plagiarizing the 1989 song. However, Madonna herself supported the younger artist and even performed a mash-up of the two songs live.
“Express Yourself” also sealed peace between Madonna and Pepsi, but only in 2016. The track was used by the company in a commercial during the Super Bowl final that year.
4) “Ray of Light”
“Ray of Light”the title track from the 1998 album, features a very different Madonna than fans were used to until then. A series of changes in her personal life — especially the birth of her daughter Lourdes — and work in cinema in Avoid (1996) also led to changes in his artistic work.
With a more electronic feel, the track is inspired by “Sepheryn”a techno song by the British duo David Curtis and Curtiss Muldoon. They were credited as songwriters on Madonna’s version, which she told Billboard (via Songfacts) about the original track:
It’s completely out of control. The original version is over 10 minutes long. It was completely indulgent, but I loved it. It was heartbreaking to have to cut it down to a manageable length.”
The lyrics, in turn, contain references to Eastern mysticism and esotericism, which Madonna became interested in in the mid-90s. It was at this time that the singer began to base her life on the teachings of Kabbalah, an esoteric movement that originated in medieval Judaism.
This time, there were no controversial clips or mega-productions. The video for the track only featured images of various cities around the world, with Madonna singing the song. Even so, the direction of Jonas Akerlund had an effect and the production was one of the highlights of that year’s MTV Video Music Awards.
5) “Vogue”
Finally, Madonna quoted “Vogue” as one of their most iconic songs. The track was released in 1990 as part of I’m Breathlessan album inspired by the film Dick Tracywhich also serves as the soundtrack for it.
The singer appears in the film, where she met the director and actor Warren Beatty. To Rolling Stone USAthe artist said that the idea behind the song came from him:
I wrote it when I was doing Dick Tracy. After we shot it, Warren Beatty asked me if I could write a song that would fit my character’s point of view, which she could have created. She was obsessed with low-key bars and movie stars and stuff like that. The idea for the lyrics came through that request.”
Despite the direct connection, “Vogue” does not appear in the film. Even so, it gained prominence due to the video clip – a new partnership with David Fincher – and due to details in the lyrics where Madonna mentions old movie stars. It did not take long for the song to become a hit and become part of the artist’s shows, always featuring prominently on the setlist.
The title “Vogue” comes from “voguing”, a type of dance that was very common in gay bars at the time, where people would stop at certain moments to pose inspired by models in magazines. Madonna became interested in the dance style, which also appears in the video, and launched an entire trend in the early 90s, alongside the producer and DJ Shep Pettibonewith whom she signs the song.
Collaborated: André Luiz Fernandes.
Source: Rollingstone

Earl Johnson is a music writer at Gossipify, known for his in-depth analysis and unique perspective on the industry. A graduate of USC with a degree in Music, he brings years of experience and passion to his writing. He covers the latest releases and trends, always on the lookout for the next big thing in music.