Madonna at 60: Ten greatest songs from the Queen of Pop

She’s been making music for 36 years and is one of the great survivors of a notoriously fickle business, staying vital and relevant by constantly pushing the boundaries of pop culture

The singer has sold more than 300 million records worldwide (Getty)

Madonna, the most successful recording female artist of all time, turns 60 on 16 August. She’s been making music for 36 years now, and is one of the great survivors of a notoriously fickle business, staying vital and relevant by endlessly reinventing her persona and music and constantly pushing the boundaries of pop culture.

A trendsetter and also a trend enhancer, with an unmatched ability for capturing the zeitgeist with her music, Madonna has long been a figurehead for female empowerment, fearless in the themes she tackles in her songs, and as she has recently proved with her outspoken speech about ageism, still willing and able to spark debate on uncomfortable subjects.

Crucially too, she has always been in control of her music. When she arrived on the scene in the first half of the Eighties with a nascent talent and a wealth of raw ambition and attitude, there was a vacancy for a strong female pop icon – a position that Madonna was happy to fill.

The video age was perfect for Madonna – perhaps no other artist personifies the MTV age more, and it’s undeniable that her videography played a huge role in the success of her music.

To celebrate her 60th, this playlist consists of just 10 Madonna classics, all of them singles – because that’s what she has always done best, and all of them inexorably linked to memorable videos. With so many classics to pick from, everyone will have their own ideas of a perfect 10 from the queen of pop, but this is my list of the 10 greatest Madonna songs.

10. Like a Virgin (1984)

Although she had previously hit number two in the UK with both “Holiday” and “Borderline”, it was with her second album that Madonna really found her groove, with the title track in particular and its accompanying provocative video planting her image of coy sexuality firmly in the public consciousness.

Produced by Nile Rodgers and composed by Tom Kelly and Billy Steinberg, the songwriting duo responsible for “True Colours” and “Eternal Flame”, “Like a Virgin’s” meaning was taken the wrong way, according to Madonna, who rejected the controversial sexual element attached to the song, explaining that she was singing about how something made her feel brand new and fresh. Whatever the meaning of the lyrics, “Like a Virgin” became an early signature song and Madonna was on her way to becoming a global superstar.

9. Hung Up (2005)

For the most recent song on this playlist, Madonna sought permission from Abba’s Benny and Bjorn for the sample of “Gimme! Gimme! Gimme! (A Man After Midnight)”, which along with the incessant thumping rhythm track gives the song its hypnotic, danceable quality.

The result was one of Madonna’s biggest ever floorfillers, defiantly turning back the clock to the disco pop sound of the 1970s that inspired early dance classics like “Holiday” and “Into the Groove”.

There’s some highly personal lyrics in there as well but the overall feeling about a record that has now sold an incredible 9 million copies and topped the charts in 41 countries, was that after the disappointing American Life album, the queen of pop had found her groove again.

8. Frozen (1998)

The mid-Nineties saw Madonna exploring other avenues like her own Maverick record label and a film career which at last won her deserved critical acclaim for her performance in Evita. She then stepped away from the limelight following the birth of her first child, but as the decade drew to a close, she was ripe for a new challenge.

She found it with her reputation enhancing collaboration with William Orbit in what amounted to an artistic rebirth. The resulting album Ray of Light is viewed by many critics and fans as Madonna’s finest album, with haunting ballad “Frozen” a particular highlight.

Featuring an icily atmospheric vocal from Madonna as she sings of being “frozen” out by cold and unemotional people and greatly enhanced by Craig Armstrong’s string arrangement incorporating eastern musical elements, “Frozen” was released as the lead-off single from Ray of Light and returned Madonna to the top of the charts on the back of a typically memorable video.

7. Music (2000)

There was no resting on laurels for Madonna after her dazzling reinvention with Ray of Light as she entered the new millennium with a glance back to the dance pop that made her with this monster clubland hit, the title track from the album that heralded her “urban cowboy” phase.

Like the majority of the album, the anthemic “Music” was a collaboration with French electronica maestro Mirwais Ahmadzai, with Madonna’s lyrics celebrating the unifying power of music regardless of creed, colour or sexual orientation.

6. Into the Groove (1985)

A cowrite with sometime boyfriend and frequent collaborator Stephen Bray, “Into the Groove” was originally recorded for the soundtrack for Desperately Seeking Susan, Madonna’s first major film. The lyrics and the irresistible beat of Madonna’s first number one say it all really. A song about the sheer joy of dancing and fittingly the pinnacle of the classic run of Madonna dance singles of the 1980s.

For an alternate take, check out the version on 1987’s You Can Dance compilation, which will keep you dancing for a full eight and a half minutes.

5. Vogue (1989)

A muscular club groove propels this irresistible homage to old-style Hollywood glamour, which also brought voguing – the “strike a pose” dance style mentioned in the song’s lyrics that was popular in the New York gay club scene of the era – into the pop mainstream.

“Vogue” also celebrated the liberating effect of dancing, and as you would expect from the queen of the promo film, the video is a classic, with Madonna striking the pose of the icons – Garbo, Monroe, Dietrich et al – she namechecks in the song.

4. Ray of Light (1998)

“Magic happens when we get into a recording studio together,” Madonna has said of her relationship with electronica svengali William Orbit, and the swirling title track of her first studio album in over three years is some kind of magic.

With lyrics reflecting Madonna’s new-found spiritual enlightenment, “Ray of Light” is a dizzying amalgam of trance, disco and Euro-pop that perfectly demonstrates her magpie type gift for taking an established genre and enhancing it.

3. Papa Don’t Preach (1986)

Controversial at the time for its teen pregnancy theme, which outraged the self-appointed guardians of morality and the widely held belief that it was an anti-abortion statement, “Papa Don’t Preach“ proved that Madonna could provoke debate over far weightier subjects than her risque videos. The artist herself foresaw the ensuing fallout, predicting in a prerelease interview that “‘Papa Don’t Preach’ is a message song that everyone is going to take the wrong way”.

For Madonna herself, in life and in her art, that message may just be that a woman is entitled to make her own decisions and be willing to take responsibility for her own actions.

2. Live to Tell (1986)

A huge leap in vocal and compositional maturity, “Live to Tell” is one of Madonna’s most personal songs as she describes the painful burden of living with (unspecified) secrets from her past and having the strength and fortitude to survive.

Singing in a lower register, Madonna invests “Live to Tell” with a naked emotion, while the unconventional structure and moody synth hook add to the haunting power of one of the great soul-baring ballads.

1. Like a Prayer (1989)

For her greatest song, Madonna fearlessly drew on two of her favourite subjects, sex and religion, for a seamless and beautiful fusion of pop, dance and gospel, with a strong anti-racist theme that inevitably provoked huge debate and furore.

Much of that was down to the notorious video featuring Madonna kissing a black saint, making love on a church altar, experiencing stigmata and dancing in a field of burning crosses. The fallout over the video led to Pepsi cancelling a recently inked contract with the artist as she was assailed from all sides by outraged moralists.

But Madonna triumphed in the end, with the video being aired constantly on MTV and the anthemic and inspirational “Like a Prayer” single topping charts around the world. She had also proved herself as an ace manipulator of huge conglomerates like MTV and Pepsi, but more importantly was now accepted by the critics as a serious and important artist.