Madonna’s first great song isn’t one of her greatest performances. It feels odd saying that, given that choosing 10 of her best songs is, if you like her, almost impossible. She’s been so many different Madonnas, after all. There’s the sculpted dominatrix, glossy in monochrome, with music to match. The Marilyn Monroe mole above the lip. The ambitious pop blonde. The wild-haired, bindi-wearing hippy, trailing the soft edges of trip-hop, the Che Guevara-loving politico mining the edges of electroclash, the mum in pink neon Lycra exploring her disco roots … and the scrappy punk drying her armpits at the hand-dryer in the ladies’ loo – the Madonna I first fell in love with. We lost my first scrappy pop-punk Madonna by her third album, True Blue, in 1986. After that, Madonna became the Icon, the Brand, the Untouchable Being. Her music generally became better after this, but her earlier songs had moments, too: the jerky, awkward peppiness of Everybody, the electronic fizz of Lucky Star, the Nile Rodgers-assisted career-breaker Like a Virgin, the perennially lemonade-fresh Holiday. Borderline, however, was something else. Written by the producer of her first album – and ex-Miles Davis Electric Band session player – Reggie Lucas, it introduced a new quality to the Madonna catalogue: an iridescent melancholy that would feed her greatest music. A boy is playing with her heart, holding her in his arms, and then driving her away, and we had to just “try to understand” that she’s “given all” she can. Madonna’s vocals aren’t as emotionally charged as they could have been here, and they’re on the squeaky side. Still, they have a powerfully steely defiance – a quality that would serve her well for years to come.



Cue the strings. As well as having a Warholesque cover image, True Blue launched itself into the stratosphere with a full baroque orchestra in its opening seconds, a surefire sign of an album aiming to take its star to higher places. Then a family drama began: “Papa, I know you’re going to be upset …”. Madonna’s epic tale of a young girl getting pregnant underlined that she was a fine provocateur, but it also harked back to girl-group ideas of young women being in difficult situations. That concept now came with a twist: this was a girl fully in charge. That’s not to say she hadn’t experienced vulnerability (“I’m in trouble deep … I’ve been losing sleep … my friends keep telling me to give it up”), but she’d made up her mind: she was keeping her baby. It was an attitude that struck people then, including those much younger I was. The video for the song is fantastic, painting an everyday New York City story of a girl and her father, while hinting at the motherless life the young Madonna had (her mother, who bore the same name as her, died when she was five, as she would go on to remind us on many songs).

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Live to Tell is a peculiar song, written for an unspectacular crime drama, At Close Range, starring Madonna’s recently acquired husband, Sean Penn. A testament to the icy, dramatic power of the 1980s synthesiser, it’s a ballad that stops and starts, freezes and then gathers pace in an epic middle eight. Producer Patrick Leonard brought the shape of the song to her (a practice they would repeat as collaborators right up to Ray of Light in 1998). Madonna wrote the lyrics to Live to Tell alone, in one go, in the studio, making the song about childhood scars and an experience that is never fully articulated. She immediately recorded the vocals, the bulk of which – bruised and wavering – made the finished single and give it a raw power. As for what this song is about, Madonna’s both admitted and denied that it’s about memories of her parents. Before the 1987 Who’s That Girl? tour, she told Rolling Stone: “It was also about being strong, and questioning whether you can be that strong, but ultimately surviving.” In 1996, she told Spin that Live to Tell was her favourite composition, “because it sums up all of my yearning and a lot of my pain”. (Her least favourite was Material Girl: “Barf. To this day when I’m walking in Central Park, a bunch of construction workers on a lunch break will see me and go, ‘Hey Material Girl!’ Oh help.”



Madonna’s first studio album for three years began, once again, with extra musical clout, but with a gospel choir replacing the strings this time around. They appeared after a short section of squalling guitars, cut short by a slamming door, as if a heavenly sign had suddenly arrived out of the noise of her life. Madonna had just turned 30 and her marriage to Penn was breaking up. She knew that “everyone must stand alone”, and that all kinds of people craved for someone to guide them. It makes sense that Like a Prayer began as a vehicle for Madonna’s voice and an organ alone. In its best version – on the original Like a Prayer album – the beats cut out for the second verse, which reveal the disarming innocence of her delivery. “Just like a child,” Madonna sings tenderly, “you whispered softly to me.” Who was she hearing? A father, a lover, or – as she asked at the start of Shep Pettibone’s remixed version on the Immaculate Collection – “God?” You’d vouch for all three. Madonna has always been the master of making ambiguity, and the simile, encourage pop culture controversy. It was no accident either that this was her second “Like a …” song. Much has been written on the clash of sex and religion in the lyrics of Like a Prayer, let alone its breathtakingly brilliant video: “I’m down on my knees / I want to take you there …” (Oh, really?). But the song’s sense of vulnerability is what really makes it pack a punch. “Feels like flying … it feels like home” – they’re like the words of The Wizard of Oz’s Dorothy whizzed through the tornado, ending in a place much more colourful, much more grownup.

A song from the terrible Dick Tracy movie shouldn’t have lasted so long, and Hanky Panky and I’m Going Bananas really, really haven’t. But Vogue is something else. This is Madonna the magpie doing what she does best (or worst, depending on your perspective): taking an underground scene mainstream. Voguing began life as part of drag ball culture in 80s New York, in a gay club scene ambushed by the physical and psychological terrors of Aids. Groups of men belonged to “houses”, in tribute to fashion designers they admired, and danced competitively against each other, striking poses for fun. Madonna had trumpeted the virtues of dancing before – “Only when I’m dancing can I feel this free,” she said – but Vogue’s first verse shows how this dancing was most vital kind of recreation: “Look around, everywhere you turn is heartache / It’s everywhere that you go / You try everything you can to escape / The pain of life that you know.” In a recent interview with Billboard – his first in 20 years – Shep Pettibone revealed: “[Voguing] was almost kind of over at that point. At least in the underground dance scene. Not over, but it had been done.” This was the first time she had worked on original material with Pettibone, after he had remixed many of her songs; they had been asked to make a B-side to the Dick Tracy soundtrack song Keep It Together for $5,000. “The whole thing was really done on a shoestring,” Pettibone told Billboard, saying they used a friend’s home studio in New York. “They had converted a closet that had bi-fold doors on it. They had put a sliding glass door on it, and that was the vocal booth … [and] only a few of the [multitrack recorder] cards were working right, because it was a secondhand machine. ” From such basic surroundings came Madonna’s glossiest moment – appropriate for the song’s message, really.

The mid-90s weren’t completely dry for Madonna. My teenage years were soundtracked by the brilliant Deeper and Deeper, the sly, seductive Secret, and my own favourite from that time, the slick, defiant hip-hop-flavoured Human Nature. But she didn’t write anything truly fabulous until 1998. Ray of Light remains one of Madonna’s best and most rewarding records, it following the birth of her first child, Lourdes, and just before she turned 40. The album sounded grownup in a diverting new way. William Orbit’s production also suited her voice, giving its wavering sensitivity an unearthly edge. This technique worked best on Ray of Light’s first single, the magnificent Frozen. For the first time in years, it wasn’t a song about Madonna, or fame, or sex, really. It was about the lack of these things in a relationship, and Madonna, of all people, wanting to warm somebody up. The beautiful string and synthesiser arrangement by Craig Armstrong – then best known for his work with Massive Attack and on Baz Luhrmann’s Romeo + Juliet – also nodded towards Madonna’s new interests in eastern mysticism, while avoiding pretentiousness. “Give yourself to me,” Madonna sang. Lots of us wanted back in.

The album’s title track couldn’t feel more different than Frozen, despite the first verse’s lyrics. These didn’t come from Madonna, though, but a much earlier English folk duo called Curtiss Maldoon. Clive Maldoon’s niece, Christine Leach, had been working with William Orbit in 1996; she starting singing her uncle’s lyrics along to one of the Madonna backing tracks. Orbit sent the tape with Leach’s contributions to Madonna; she kept the first verse and chorus pretty much as they were. Leach’s uncle eventually got 15% of the royalties for Ray of Light. But there’s more to this track than the mindbending lyrics. It’s a song that wriggles and squirms – not verbs you’d naturally associate with Madonna – and has a sense of joy and life that isn’t hampered by defensiveness or cynicism. The chorus (accidentally) and Madonna’s second verse (purposefully) also nod to Like a Prayer. “Faster than the speeding light she’s flying”, it goes, “and I feel like I just got home.”

Including three tracks off Ray of Light seems excessive, but it’s hard not to when they’re this good. The album’s last track, Mer Girl, is also a special Madonna oddity. A song written about death that comes over like a particularly dark piece of 70s psychedelia in its lyrics, you’d expect something like it to come from an artist much more like Kate Bush (who is only a fortnight older than Madonna, although her career began much earlier). “It’s a song about dealing with death,” Madonna told Q magazine in 1997. “There’s the obvious thing about my mother’s death, but also Princess Diana and Versace’s deaths … There seemed to be so much death actually around the time that I wrote it.” Mer Girl begins with a sound that suggests a distant, eerie telephone – messages from the deep – and a woman running away from her mother (“who haunts me, even though she’s gone”), a man she “cannot keep”, and a daughter “who never sleeps” (perhaps baby Lourdes?). Through the lake and the forest she goes (“I was looking for me”), and she ends up at a cemetery, among crumbling tombstones. Here the ground gives way, leaves cover her face, ants march across her back, and she smells her burning flesh, rotting bones, decay, and runs away. It’s an extraordinary, terrifying and affecting mood piece. “I was very proud of it,” Orbit told Q in the same interview. “And there was outside pressure to change it,” he added, “but Madonna said, ‘No. It’s a piece of art. Don’t touch it.’”



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Madonna’s eighth album, Music, had several successful flirtations with the countrified guitar, including the lovely I Deserve It (later covered gorgeously by Britta Phillips and Dean Wareham) and the deconstructed Sweet Home Alabama-stomp of Don’t Tell Me. Madonna’s 21st century has largely, however, been all about the beat, and the second track from Music, with its fabulous LFO sweeps and Korg synthesiser mangles, is still one of the best examples of Madonna trying a more hardcore club sound. Mirwais is at the controls, and has tons of fun with her voice, stretching it, slicing it, compressing it, freeing it in many ways – she’s never been an opera singer after all, despite several valiant attempts. The lyrics also possess a sense of fun; they are nice palate cleansers after all that recent spirituality. There is a nice, spontaneous raunch about the first verse particularly: “The universe is full of stars / Nothing out there looks the same / You’re the one that I’ve been waiting for / I don’t even know your name.” There’s also something charming and silly about hearing a woman who has brought debate about sex and religion and race into the mainstream singing: “I like to singy singy singy / Like a bird on a wingy wingy wingy.”

I fell out of love with Madonna in 2008 after Hard Candy, despite trying to convince myself it was brilliant. Confessions on a Dancefloor, in 2005, marked the last time I thought Madonna did what she does best: took something from popular culture and made it new. The idea behind Hung Up was a risky one, too: base the lead single or a new album around an Abba hook. But while the track looked back at the disco days of Gimme! Gimme! Gimme! (A Man After Midnight) in its slight disco sensibilities, it also looked forward. Take away the sample (as you can here, by hearing Madonna and Stuart Price’s demo), and that dirty, pulsing bassline takes it towards house (“time moves on, so slowly”), and onwards to the glittery, modern-day mainstream. There are some fantastic remixes from Confessions on a Dancefloor, including the Pet Shop Boys’ Maxi Mix edit of the album’s second single, Sorry, but the true Hung Up thumper is by Spanish DJs Chus & Ceballos. It’s also a reminder of that girl who could dance for inspiration.