Madonna at 60! 20 of our favourite songs

Madonna at 60! 20 of our favourite songs

Madonna Louise Ciccone  turns 60 years old today. The genre-blurring, age-defying Queen of Pop has over her thirty-five-year career forged her own path through the sheer force of her personality, reinvention and ambition. Throughout the last three decades, her shifts in style, sound and live performances have challenged sexual and religious taboos and in the process she has become an inspiring feminist icon. Whilst it’s fair to say her later years have been more characterised by her attention seeking, dubious film roles and hit and miss material, it’s impossible to overlook the impact Madonna has had on popular culture and society, plus like an old friend you can return to time after time her back catalogue is crammed full of brilliant pop songs. To celebrate we have selected some of our favourite songs.


Holiday (1983)

It isn’t my favourite Madonna song, that’s ‘Like a Prayer’ followed by ‘La Isla Bonita’ but ‘Holiday’ is the first Madonna song I ever heard, I suppose that’s the case with most people, but in unusual circumstances. I was in New York – in the ‘fall’ as they say over there – in 1983 with a group of people on a business trip and we (and especially I) somehow managed to get into Studio 54. I remember being halfway down a flight of stairs when I heard it being played and wondering who it was, comparing the singer with Cyndi Lauper who had just established herself with ‘Girls Just Want To Have Fun’ and who, in my opinion, would have been a bigger star had Madge not suddenly arrived on the scene. The next moment I slipped and slid down the rest of the stairs butt first as they say over there. I wasn’t surprised it was a hit but I didn’t expect Madonna to be the star she became at that time.

Not long after, she turned up at the Hacienda in Manchester and performed ‘Holiday’, her first ever UK live and TV appearance. I wasn’t there that night but recall a dope head I knew at the time telling me “she’s something else, man”. Apparently, she was paid £50. (David Bentley)

Borderline (1984)

I could have chosen ‘Like A Virgin’, Madonna’s breakthrough 1983 hit, produced by drug-taking studio genius and 80s super producer Nile Rodgers (the dude behind 70s disco legends Chic, who would later produce Bowie and Duran Duran), as its significance for female empowerment inspired Masters degrees. But I love this record. There’s an innocence and simplicity about it – it doesn’t rely on the big controversial concept video that she became known for (‘Like A Prayer’, ‘Vogue’, etc), and which indeed became the template for later stars, including latter day Madonna-inspired, Lady Gaga. Instead, ‘Borderline’ is about as perfect a pop record as she or anyone else has ever made. (Abbas Ali)

Into The Groove (1985)

Originally on the soundtrack for her 1985 film Desperately Seeking Susan, ‘Into The Groove‘ featured on the re-issue of her second studio album, Like a Virgin (1984), outside North America and became her third single released in 1985 when it topped the charts.

And you can dance for inspiration‘ she declares to usher in ‘Into The Groove’, an exciting disco classic and self-empowering anthem for dancing like nobody is watching. It’s underscored by Madonna’s bitter-sweet unrequited longing and love of club culture; it was one of early Madonna’s first few steps into embodying a role as dance floor queen. On the surface an upbeat neon floor-filler yet there’s a contradiction about ‘Into the Groove.’ On the one hand, she sings about dancing on her own at home, but on the other, she’s embodying the freedom of dancing in the crowd, a sensuality and infatuation. The line ‘You’ve got to prove your love to me’ is perhaps the first hint of Madonna’s ability to take the lead role, turn the tables on her male companions; it’s a strand that she would explore later in her work. Like the cool, brightly coloured charity shop style she rocked early on, young Madonna makes much of a very simple melody, punctuating a bubbling palette of ’80s synths, killer basslines and drum machines that were the height of fashion at the time, her emphasis on words with power ‘free’, ‘ME’ ,’dance with someone else’ show her ability to take what is a very unassuming song and turn it into a stone cold dance-pop classic, it’s a strength Nile Rodgers would later pick up on when she turned ‘Like a Virgin’ into a worldwide smash, partly through the sheer quality and personality of her vocal performance. There’s a nascent youthfulness to ‘Into The Groove’, a promise, and a hint of the artist and person Madonna would become, it still sounds great. (Bill Cummings)

Material Girl (1985)

When super producer Nile Rodgers refers to Madonna’s second album ‘Like a Virgin’, he calls it another Chic record. Certainly, their paw prints are all over the title track and this awesome hit; her vocals are strident and cheeky here matching the funky combination of basslines and bounding synths. There’s playfulness to the robotic call and return chorus (‘living in a material world’) reflecting the song’s message, that her love can be bought by material possession as she chooses a life of decadence rather than romance and an assertion that she was in control of her own destiny rather than any man. This theme was reflective of her life of fame and fortune at that time and thus appealed to Madonna’s provocative personality. It’s since been seen as defining Madonna as an feminist icon along with ‘Like a Virgin’.

With the look of the memorable video riffing on a pastiche of the Marilyn performance of ‘Diamonds Are A Girl’s Best Friend’ from the movie ‘Gentlemen Prefer Blondes’, it’s undercut by scenes featuring a director trying to win the heart of an actress, played by Madonna herself. Contrary to the song, the young woman is not impressed by money and expensive gifts, but by pretending to be poor he ends up taking her on a date. This was part of Madonna’s imperial phase and an unforgettable earworm to boot. (Bill Cummings)

Papa Don’t Preach (1986)

In 1983, Madonna released her debut The First Album; it was not only a glistening war cry on the charts, but also something that insinuated a continuation in title alone. The singer, actress and entrepreneur didn’t fail to keep her promise: since her inception at the turn of the decade, she’s released a host of follow-ups, including 1984’s Like A Virgin, which is internationally hailed as a masterpiece and is a phenomenal embodiment of 1980s pop music.

Although most now associate Madonna with sinew, faux pas spandex and dubious film appearances, during her formative years she challenged the Church’s modern convention, and also the public’s perception of pop music, women and Generation X – teens previously described as laborious and dangerously liberal found new hope in the Michigan native’s challenging artistic credentials and flamboyant dancing. She was without a doubt one of the 1980’s most important finds. (Tiffany Edwards)

Like a Prayer (1989)

‘Like a Prayer’ is a very important song to me. I felt the impact that it was going to make. That song means a lot more to me than ‘Like a Virgin’. I wrote it and it’s from my heart. It’s a very spiritual song. I think I was much more spiritually in touch with the power of words and music by the time I started recording the song and the album.” Madonna told Billboard. ‘Like a Prayer’ is perhaps the zenith of Madonna’s pop artistry and maybe her greatest song, reflecting her own life more vividly than in the past, she was going through a messy divorce from Sean Penn at the time, she had also turned 30, the age at which her mother had died. Thus the songs symbolic imagery and complicated relationship with Catholic guilt took on a greater resonance and earned her the critical praise that had eluded her previously.

According to her it’s about a young girl “so in love with God that it is almost as though he were the male figure in her life.” With deep religious imagery laced various (sexual) double meanings (‘I’m down on my knees’) and the controversial video with its depiction of burning crosses and kissing the statue of a black saint, Like A Prayer challenged taboos and made quite an impact, with religious groups campaigning to have the video banned from MTV. But most of all this devotional marriage of evocative, confessional organ dappled verses are sophisticatedly weighted against soaring gospel led communal choruses and Madonna’s exquisite vocal, it’s a powerful, unmissable single underscored by her conflicted relationship with love, guilt and Catholicism. (Bill Cummings)

Dear Jessie (1989)

OK, so it’s not her very best by several country miles, but it is a cute song with a video to match.  August 1989, my sister had her 18th birthday party at a local nightclub called The Brunswick in one of the busiest streets in Great Yarmouth, Norfolk.  As it would turn out, The Brunswick was a place we’d both end up spending a large chunk of our late teens and early twenties.  But in 1989 I was seven-almost-eight and ‘Dear Jessie’ was something I’d heard a few times and really liked it, so much so I begged and pleaded with the DJ to play it at the party, and I spent the entire song flitting and spinning about and having the best time ever.  Another thing my sister and I shared was a love of the Saturday show very efficiently titled The Chart Show where they would play videos of songs in the charts, etc.  And that’s where I saw the video for the first time.  And, as a seven-year-old with a very creative imagination, I thought it was the most wonderful thing I’d ever seen.(Toni Spencer)

Express Yourself (1989)

As a teenager at the tail end of the eighties, it’s probably true that the notoriously sexy video and equally erotic imagery on the record’s picture disc were, at the time, as much of a draw to me as the song itself. But if you strip all that malarkey away and listen to the song now, almost thirty years later, then oh my goodness, ‘Express Yourself‘ has held up remarkably well indeed! That instantly immediate refrain of “Don’t go for second best baby, put your love to the test” sets her stall out from the get go, the very much ‘of the time’ synth and (briefly) sax complementing each other perfectly in what must be amongst the greatest dance records of that decade. (Loz Etheridge)

Till Death Do Us Part (1989)

Whist Madonna has more classic hit singles than most, it’s worth remembering how brilliant her albums could be too. After three excellent and successful albums, she made her most ambitious release to date, Like A Prayer (the album where music critics got onboard). It contains some of her best singles (‘Oh Father’, ‘Express Yourself‘ and the iconic title track). It also has her greatest deep cut, ‘Till Death Do Us Part‘, which if it had been released as a single, would have no doubt been another top five single. It’s one of her catchiest songs brimming with cool little production details. The flickering synths, shiny guitars and an infectious bass-line. The upbeat is a contrast to the story of a relationship coming to an end. Madonna sings the heartbreaking lyrics, “the bruises they will fade away, you hit so hard with the things you say. I will not stay to watch your hate as it grows”. Her impressive vocal range is on display as she switches from cool detachment to yearning heartache within seconds on this perfect song. (Jonathan Wright)

Vogue (1990)

This is the definition of a guilty pleasure. Not because there’s any intrinsic shame or disgrace in listening to it, but it’s just too problematic to wave through. Madonna’s recent social media activity suggests someone struggling to keep up with social justice issues in 2018 but she was never #woke really: how else could you explain the list of icons being nearly exclusively white here? And it’s very easy for a megastar removed from every real-life struggle to tell you that privilege isn’t real – because actually, it does make a difference if you’re black or white, if you’re a boy or a girl. But when those bouncy swinging piano chords come in, coupled with those strident blasts of horn and Madonna’s vocals of swirling abandon, it’s impossible to resist. ‘Vogue‘ was one of the earliest pop hits to draw from house music and even if she didn’t quite get the politics right, her role in bringing queer culture into the mainstream can’t be underestimated. In recent years we’ve had a lot of mediocre pop hits from patronising divas about loving yourself with a LGBT subtext (‘Born This Way’, “Firework”, “We R Who We R” etc). None of them captured the rapturous hedonism of dancefloor freedom like ‘Vogue’ does and that’s why it’s so easy to overlook its flaws. (Scott Ramage)

Justify My Love (1990)

It rarely gets mentioned in Madonna run-downs but ‘Justify My Love’ remains one of the most important tracks in her whole canon.  As the lead single off The Immaculate Collection (the greatest hits selection that cemented her as an icon) it marked a cut from the past and pointed to the future. A reworking of Prince protegé Ingrid Chavez lyrics, and boosted by Lenny Kravitz’s music and production, it tapped into the rise of trip-hop announcing Madonna as a serious artist and pop chameleon. Seductive mid-temp beats (nicked from Public Enemy and slowed down) and Madonna’s move to breathy, almost spoken vocals rode the 1990 zeitgeist effortlessly and paved the way for the pure-sex controversy of Erotica, and her dance excursions in the future. (James Thornhill)

Take A Bow (1994)

Take A Bow‘ is my favourite Madonna single, because it’s a song where she lets her guard down and gives one of her most vulnerable performances. Over rich swirling strings, she sings in her deeper register with such control and class that shows what an underrated vocalist she is. The production is incredibly lush and the melody romantic as she’s joined by Babyface on backing vocals. He provides heavenly harmonies that result in one her best choruses (and Madonna has made a career out of incredible choruses). This gorgeous winter ballad is her most touching story of love and rejection with direct lyrics, especially how she sings, “I’ve always been in love with you, I guess you’ve always known it’s true” with such clarity. It’s the perfect closer on her most underrated album, Bedtime Stories. (Jonathan Wright)

Bedtime Story (1994)

At best barely remembered for its Bjork co-writing credentials and for being the almost-title track of her 1994 album, Bedtime Story‘s  lost status does a disservice to its many delicacies. Definitely Madonna’s most adventurous single to that point, its ambient electro pulse, obtuse phrasing, underrated “let’s get unconscious, honey” hook and eye-popping multi-million dollar video were rewarded with it being her first single in an age to miss the Stateside top 40. If any of her singles has “rediscover me” tattooed through it, it’s this one. Go get unconscious. (James McLuckie)

Human Nature(1994)

Human Nature’ is the dark side of ‘Express Yourself’ – furious, cynical Madge licking her wounds after being shamed for expressing herself a little too much for the conservative world to handle. It’s probably the most explicitly unapologetic moment of her career and its confrontational pose is a hard sell, but when did that bother her? Dismissing her critics with a mocking nasal whine, whispering her sarcastic quips like coy come-ons, in a video leaning hard on BDSM imagery, it’s also the sexiest thing that she ever did. Not because of the outfits or the language but the confidence: an icon of feminist ideals, owning her identity without guilt or fear. (Scott Ramage)

Ray Of Light (1998)

By the late nineties, Madonna was obviously already a bona fide superstar, yet her stock had fallen somewhat, with some less than triumphant roles in big screen turkeys like Body Of Evidence and Four Rooms, while her leading performance in Andrew Lloyd Webber’s Evita met with mixed reviews from critics, despite receiving a Best Actress award at the Golden Globes. It was a fairly barren period musically for a few years too. Enter one William Orbit, who rejuvenated the honorary New Yorker so magnificently that ‘Ray Of Light’ erred on the right side of ‘masterpiece’, even if lots of us (including me, I must sheepishly admit) did at first think she was singing about Anna Friel. Its parent album, of the same name, was one of the best releases of 1998. (Loz Etheridge)

Drowned World/Substitute For Love

Stately as she goes, Madonna opened her watershed Ray of Light opus with electro bubbles, mediations on the cost of fame, an (unwise?) interjection of drum and bass, and a quiet rage that many, coming so soon after all of that Evita thespian malarkey, had decided she was never showing again. Beautiful by anyone’s standards, she exercised hopeless judgment by excluding it from 2009’s patchy Celebration hits compilation. Nonetheless, the controversial Princess Diana evoking video, and it adorning her Drowned World Tour with its moniker, affords it a much-deserved legacy of some sort. (James McLuckie)

What It Feels Like For A Girl (Original Album Version) (2000)

After the critical and commercial success of Ray Of Light (Madonna’s third imperial phase), Madonna kept the momentum going with Music. She released the album’s understated highlight as the third single even though it wasn’t an obvious hit. The music is made up of dreamy synths, sensual deep bass and a glitchy rhythm. The lyrics are hard-hitting as Madonna sings about the unfair double standards and issues of being a woman, “strong inside but you don’t know it, good little girls, they never show it. When you open up your mouth to speak could you be a little weak”. The Charlotte Gainsbourg sample at the beginning makes the message even more effective. Almost 20 years into her career Madonna was as vital as a pop star as she’d ever been. It was even more impressive how effortless she made it all sound on one of her most warm and beautiful songs. (Jonathan Wright)

Impressive Instant (2000)

It’s difficult to pick a definitive should’ve-been-a-single track from Madonna’s back catalogue. ‘Skin’ and ‘Till Death Do Us Part’ get extremely honourable mentions. However, this bouncy, bonkers cut from 2000’s Music gets the nod. Set to be that album’s fourth hit parade conqueror, clips of its Drowned World Tour performance were distributed to build an already insatiable appetite for her first show in almost a decade, and remixes were locked and loaded, ready to fill dance floors the world over. But then a wrangle with Warners, who favoured the sub-‘Beautiful Stranger’ skip of ‘Amazing’, pissed on its pop chips and its release was cancelled. A great shame we never got to see how Madonna, in one of her most artistically satisfying phases, would have visually represented “I like to singy, singy singy, like a bird on a wingy, wingy, wingy.” (James McLuckie)

Hung Up (2005)

As someone whose little eight-year-old mind was well and truly blown by the video for ‘Like A Virgin’, it’s quite hard to pick a favourite Madonna track. But ‘Hung Up’ is a serious contender.

Released in late 2005, ‘Hung Up’ is the opening track on the stunning and aptly-named Confessions On A Dance Floor. By this stage, Madonna had been a fixture in our lives for over two decades, and this was another example of why she continued to be the queen of pop: she made brilliant records. Twenty years after ‘Into The Groove’ became her first U.K. no.1, this was yet another chart-topper.

It is a fine example of 1970s disco combined with 1980s pop, reportedly selling over nine million copies worldwide. Madonna sings of a lover who has kept her waiting, and how she has reached the point of giving up on them.

Famously, the track samples ABBA’s 1979 hit ‘Gimme! Gimme! Gimme! (A Man After Midnight).’ It was only the second time that ABBA songwriters Benny Anderson and Björn Ulvaeus had granted permission for an artist to sample their work.

On a personal level, I remember playing the newly released album at my birthday that year and just how people loved it. Speaking of which, Happy Birthday, Madonna. Long may you run. (Ed Jupp)

Sorry (Pet Shop Boys Maxi Mix) (2006)

By the time Madonna released her 10th album, 2005’s Confessions On A Dance Floor, her commercial stock had arguably dropped a little but returned in spades with the Abba-sampling ‘Hung Up’. Its follow-up though was the masterpiece for me; Madonna’s 12th UK Number 1 single came in several remixed forms, but the Pet Shop Boys Maxi Mix made a great song even better, an eight-and-a-half-minute delight that rarely gets an airing these days. Seek it out! (Andy Page)

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