Our pick of the 15 best Madonna songs, from Frozen to Like A Prayer

Madonna at the Grammy awards in 2023  (Getty Images)
Madonna at the Grammy awards in 2023 (Getty Images)

Madonna – the Queen of Pop and a modern day icon – has spent several days in an ICU after developing a serious bacterial infection.

Her worldwide Celebration Tour, which was set to kick off on July 15, has been subsequently postponed.

“Her health is improving, however she is still under medical care. A full recovery is expected,” said Madge’s manager, Guy Oseary. “At this time we will need to pause all commitments, which includes the tour.

“We will share more details with you soon as we have them, including a new start date for the tour and for rescheduled shows.”

Here, to celebrate Madge, and wish her a speedy recovery, we’ve picked 15 of her best songs, from some of her greatest early tracks to the ones that helped reassert her dominance decades later.

15. Don’t Cry For Me Argentina (1996)

People are often quick to dismiss Madonna’s acting career, but her performance in the film adaptation of Andrew Lloyd Webber and Tim Rice’s Evita saw her pick up a Best Actress gong at the 1996 Golden Globes. She wanted the part of Eva Peron, late Argentinian First Lady, so badly that she wrote a four page letter to the director and subsequently underwent vocal training for the part. It may not be the definitive version of the song (stand up Elaine Paige), but Madge gives it some gusto — and she even provided something the world never knew it needed: an obscenely Nineties dance remix of the song. JT

14. Hung Up (2005)

Madonna’s output this side of the millennium has been somewhat patchy — her 2003 album, American Life, was entirely underwhelming, and the less said about her Justin Timberlake collaboration 4 Minutes, the better. This song, though, the lead single off her 2005 album, Confessions on a Dancefloor, proved she could still come through with the hits. It’s electrified by that bracing sample of ABBA’s Gimme! Gimme! Gimme!, set against flashes of New Order’s Blue Monday in the thumping techno-pop production. It stormed to the top of the charts around the world and, all of a sudden, Madonna was a pop force to be reckoned with once again. JE

13. La Isla Bonita (1987)

Let’s get this straight: holiday romances rarely end well. Stop eyeing that dark and handsome waiter right now and listen to Madonna’s cautionary tale of falling head over heels for San Pedro – who is either a bloke with a saintly moniker, or a picturesque lump of rock in the Iberian peninsula. Either way, we’re caught up in the romance of it all, whispering sweet nothings to ourselves. AB

12. Vogue (1990)

What are you looking at? Just one of the most iconic music videos of the last forty years. Madonna is in full-on siren mode in this homage to both the screen starlets of decades past and the underground dance form that flourished in New York’s LGBT club scene. Strike a pose all you like, you’ll struggle to be as chic as anyone in this video, let alone the Hollywood legends who glitter in the song’s rap section. Should you even be reading this if you don’t know what Harlow, Jean is the picture of and where Ginger Rogers dances? AB

11. Frozen (1998)

Cold, dark and beautiful, Frozen was an expression of Madonna’s feelings of "retaliation, revenge, hate and regret". It was inspired by the 1990 film Sheltering Sky, which tells the story of a couple who are trying to save their marriage in North Africa. Top of the charts for weeks in 1997, the award-winning video was filmed deep in the Mojave Desert and sees the Queen of Pop strive to portray the "embodiment of female angst". In a nutshell, it’s the definition of the word "dramatic". LA

10. True Blue (1986)

Forget the fact she looks like Pat Butcher in the music video, this chirpy tune from Madonna’s third album (also titled True Blue) is a veritable smile party. It was her first husband, actor Sean Penn, that inspired lyrics that fuse the medical profession and sartorial choices, such as: "You’re the one I’m dreaming of/ Your heart fits me like a glove." Alas, Madge and Penn ended up going their separate ways after just two years of marriage, but their brief, tumultuous union inspired a truly excellent pop song. JT

9. Justify My Love (1990)

Notorious. Sexy. Controversial. Justify My Love is a trip-hop, mid-tempo spoken word ode to sadomasochism that still remains one of Madonna’s most alluring, unforgettable and mesmerising lyrical masterpieces to this day. Why? It oozes sex, stirs drama and commands your attention in the raunchiest and most natural way possible. Fiercely criticised and in some countries banned, Justify My Love ticks all the boxes.

The song was written by Lenny Kravitz and Prince-collaborator and protégé Ingrid Chavez, who famously culled half the song’s lyrics from a love letter she never mailed to Kravitz. Responding to the once-banned video’s controversy (MTV thought it was too sexually explicit), Madonna on Nightline said: "We’re dealing with sexual fantasies…And being truthful and honest with our partner, these feelings exist. I’m just dealing with the truth here." Madonna also expressed anger at the video’s banning, arguing that she did not understand why the music network still allowed videos that contained violence and degradation to women to continue to get regular airplay. As a result, the video was released on VHS and became a best-selling ‘video single’. Kudos to her. LA

8. Holiday (1983)

Holiday featured on Madonna’s self-titled album and became her first big hit in the States. The lyrics are hardly the most profound thing Madonna would ever sing — “If we took a holiday/ Took some time to celebrate/ Just one day out of life/ It would be, it would be so nice” — but to think too deeply about it would be to miss the point. It’s a joyously simple song, an infectious piece of synthy, saccharine funk that’s made for those breeziest of holidays — the ones where the schedule is loose, the sky is cloudless and the wine is flowing. And, like any great pop song, that hook will linger in your head long after the holiday is over. JE

7. Ray of Light (1998)

Twenty years ago, Madonna went electric. Well, electronic to be precise. After a period mid-Nineties wilderness, Ray of Light – the album and its title track – saw Madonna not only tighten her grip on her Pop Queen throne but also set her sights on conquering new lands. Soaring, euphoric and eminently danceable, Ray of Light married underground contemporary EDM with a mainstream, catchy pop structure, and set the soundtrack for almost every hedonistic party scene broadcast on television for at least three years. AB

6. Borderline (1983)

This Eighties classic from Madonna’s first album is pure joy. The video features Madonna being so annoyed at men that she kicks a lamppost, and she’s sporting what is still her greatest look: grungy glam, with big hair, big earrings and big hats. She sings "I don’t want to be your prisoner, so baby won’t you set me free", firmly placing herself as a strong woman who won’t put up with any nonsense. Only bangers this good can stand the test of time – you don’t get keyboard intros like that anymore – and it’s since been covered by everyone from Duffy to the Counting Crows. JT

5. Into The Groove (1985)

This isn’t just any dance track – this is the Madonna dance track. The beatbox anthem Madonna dreamed of writing when she squatted and ate out of garbage cans while living in New York, Into the Groove shot to the top of the charts around the world. On the inspiration behind the song, Madonna revealed: “The dance floor was quite a magical place for me... The freedom that I always feel when I'm dancing, that feeling of inhabiting your body, letting yourself go, expressing yourself through music." The song never fails to do what it says on the tin: get you into the groove. And yes, we’re dancing to it in the office right now. LA

4. Material Girl (1985)

The song that spawned a thousand lazy headlines. Not long after Madonna released this song in 1985, ‘Material Girl’ had become her go-to moniker in many parts of the press. It’s ironic, really, seeing as Madonna claimed to be anything but. She later said in an interview that she decided to present this version of herself, unbothered by true romance but obsessed with anything diamond-encrusted, as a provocation — it’s a tactic that has rarely been left out of the Madonna playbook, so you’d be inclined to believe her. Whether the song is a deceptively simple satire or simply a reflection of the world she saw around her is up for debate, but one thing is for sure: it’s a ridiculously catchy tune. That chorus lands with one of the best known hooks of the Eighties, and Nile Rodgers’ production is pneumatically bouncy. JE

3. Like A Virgin (1984)

Rewind to an infamous 1984 VMA performance and you’ll understand why Like A Virgin was met with so much controversy. A woman totally in control of her sex life on and off stage? The shock. The horror. Damned by the media and condemned by the Catholic church, Like A Virgin is Madonna’s definitive statement track and arguably made her the feminist icon she is today. Heck, it was so controversial countless family organisations throughout North America complained that the song promoted unsafe sex before marriage.

Madonna’s response? "People were thinking 'who was I pretending to be—the Virgin Mary or the whore?' These were the two extreme images of women I had known vividly…the Virgin Mary and the whore as one and all. It was a statement of independence: if you wanna be a virgin, you are welcome. But if you wanna be a whore, it's your f******g right to be so." The empowered legacy of Like A Virgin is unquestionable, so much so that some universities in North America began to offer courses in Madonna studies throughout the 1990s. It’s also a touch ironic that the song’s music video was filmed in the centre of Catholic conservatism, Venice – we’ll leave it to the academics to decipher that. LA

2. Papa Don't Preach (1986)

The world was a very different place 37 years ago, back when this song – about a young woman’s pregnancy and her grapples with the prospect of abortion – was first released. If such a topic were to be tackled in a pop song now, we’d hope it would ruffle a few less feathers (though following the Supreme Court’s 2022 ruling, who can say?). The song drew criticism from those in America who thought it glorified teenage pregnancy and even offended the Vatican to the extent that Pope John Paul II begged people in Italy to boycott Madonna’s live performances in protest. Looking back now, it’s easier to read its feminist message — it’s about a woman who had made a decision on her own, without the need for her father’s approval. JE

1. Like A Prayer (1989)

When the sacred met the sexual. It’s highly documented that Madonna has been obsessed with the connection between sex, sexuality and religious iconography and no song shows this obsession more so than the 1989 smash Like A Prayer. Its sexual and religious ambiguity is riddled within the song’s eyebrow raising lyrics: "I’m down on my knees/I wanna take you there."

The video is a cleavage-riddled epic of blasphemy, which sees Madge suggestively posed with a hot black saint statue, experiencing the stigmata and dancing in front of burning crosses. A day after the video's release, religious groups worldwide – including the Vatican – immediately protested, saying it contained obscene use of Christian imagery. Others demanded everyone involved in its making, promotion and sponsorship to be boycotted. Hey – it wouldn’t be a Madonna song without a little bit of controversy, now would it? LA