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The best Madonna songs prove the Queen Of Pop to be the ultimate chameleon, turning out classic tracks while effortlessly staying on-trend.

Sifting through more than 80 singles, 14 studio albums, countless soundtracks and compilations, selecting the best Madonna songs isn’t for the faint-hearted. The mistress of reinvention is an accomplished balladeer, an indisputable dance legend – she’s enjoyed no less than 50 Billboard Dance Club No.1s to date – and the ultimate genre chameleon, always with one eye on what’s happening next and how it might serve her.

At her peak, the pace was giddy. Name any other artist that would – or could – release singles as diverse as the whimsical Dear Jessie, the anthemic Vogue, the swing pastiche of Hanky Panky and then the steamy Justify My Love in just a 12-month stretch? While her vice-like grip on radio-play and the international sales charts might have faltered in recent years, she appears finally to be taking stock and letting her legacy do some of the shouting.

With a self-produced biopic seemingly in the works, it simply must include these 20 best Madonna songs.

20: LIKE A VIRGIN (1984)
Forever earning its place among the best Madonna songs, this Nile Rogers-produced slab of 80s dance-pop shot Madonna’s career into the stratosphere. It had been 24 months since the release of her first single, the club hit Everybody, and the subsequent breakthrough of singles like Lucky Star had built her profile nicely. But a frothy, irreverent live performance of this about-to-be-released track at the first MTV Video Awards, in September 1984, is the stuff of legend. America – and then the rest of the world – started to take serious notice. By Christmas 1984, Madonna was enjoying her first stateside chart-topper, with Madonna-mania just around the corner. 1985 was going to be her year.

19: CRAVE (FEATURING SWAE LEE) (2019)
This collaboration with the American rapper was lifted from Madonna’s 14th studio collection, Madame X, in May 2019. A dreamy hip-hop ballad built on her run of adult-contemporary hits it (predictably) topped the US dance listings, but mainstream radio’s attention was focused elsewhere. If the lack of commercial success continues to bother her, she’s hiding it well by issuing material that’s often demanding (and never less than ambitious). Crave was arguably about as accessible as much of the material on Madame X gets, but one can’t help thinking if an artist half her age had recorded it, DJs would have played it to death.

18: EXPRESS YOURSELF (1989)
One of the best Madonna songs of the 80s, this party anthem from the critical and commercial triumph of 1989’s Like A Prayer wears its 70s heart firmly on its sleeve and opened each night of the Blond Ambition tour of 1990, whose shows arguably set the template for every stadium spectacular that came after. Composed with early collaborator Stephen Bray, Express Yourself and its extravagant video benefitted from the largest budget ever green-lit for a pop promo at that time. In many ways, it was the final empowering pep talk for that first generation of female “wannabes” as they matured alongside the idol at the end of the era that continues to define her.

17: HOLIDAY (1983)
Name a party playlist that doesn’t benefit by including this summertime classic. The irony, of course, is that Holiday became an international hit across the winter of 1983, as the first crossover single from a then largely unknown disco act. Madonna crossed the globe for countless TV performances of the song, including an appearance on Dick Clark’s American Bandstand, the BBC’s Top Of The Pops, and the legendary Haçienda episode of The Tube. Good job, too, as the video recorded for the release was shelved. Don’t worry about its mistimed chart appearance; Holiday was subsequently reissued in the UK twice, making the Top 5 again in the – more appropriately seasonal – summers of 1985 and 1991.

16: GIRL GONE WILD (2012)
Teaming up with Benny Benassi for Girl Gone Wild, the second single from 2012’s MDNA, this electro-pop sizzler was a sturdy attempt to reclaim dominance over those dancefloor anthems that Madonna had once been famous for. Its Mert Alaş and Marcus Piggott video raised eyebrows and didn’t get aired much, but was adored by the LGBTQ community for its confident sexuality and gender-play. If she was playing to her crowd, she certainly wasn’t doing so entirely safely.

15: CRAZY FOR YOU (1985)
No one had seen this coming in early 1985… A ballad by Madonna? It was a genre she would make one of her signatures, but was a world away from anything that she had recorded before. This school-disco classic was recorded to support her cameo role in the long-forgotten movie Vision Quest (retitled Crazy For You for its video release in the UK – for the most obvious of reasons) and, such was Madonna’s star power in 1985, knocked USA For Africa’s bloated We Are The World off the top of the US charts – revenge, perhaps, for being left off the charity single’s line-up. In the UK, the song made No.2 twice (being issued again in early 1991 to support the release of her most successful UK album, The Immaculate Collection).

14: FROZEN (1998)
This cosmic ballad was the surprise first release from Madonna’s triumphant 1998 comeback album, Ray Of Light, produced with William Orbit. The song’s ethereal, mystic melody offered one of the singer’s strongest vocal performances to date and came off the back of gruelling Evita project, which saw her secure a Golden Globe for her part in the Andrew Lloyd Webber musical (reshaped for the big screen by the late Alan Parker). Frozen became Madonna’s first UK chart-topper in eight years and was a highlight of the Madame X tour of 2019 and 2020, concluded just as the COVID-19 pandemic took hold across the planet.

13: DEEPER AND DEEPER (1992)
Shep Pettibone’s work on the Erotica album divided critics, while sales fell short of Madonna’s platinum-standard expectation. Many were distracted by the timing of the attention-grabbing Sex book, and others were startled by an increasingly confrontational tone in Madonna’s work. Deeper And Deeper is one of the album’s lighter moments: an effervescent dance track that references another one of the best Madonna songs (Vogue) and takes its place alongside her finest party anthems. Nothing new here, perhaps, but a small gesture for those struggling with the sharp left-turn of her work at the start of the 90s.

12: GIVE IT 2 ME (FEATURING PHARRELL WILLIAMS) (2008)
The Hard Candy album was an attempt to reclaim some momentum in the US market after the relative underperformance of Confessions On A Dance Floor. Chasing a contemporary urban groove worked in her favour: the collaboration with Justin Timberlake and Timbaland on 4 Minutes might have hogged the No.1 spot around the world, but this Pharrell Williams-assisted jam was the album’s second single and did just as well in the UK, even though it ailed to match that success back home.

11: JUSTIFY MY LOVE (1990)
Issued as part of the campaign for The Immaculate Collection in late 1990, Madonna’s reputation for pushing the agenda played out in spectacular fashion here. Empowerment from sex was the message, and no one who saw the steamy video clip was likely to miss that (though you may have had to buy it on VHS, as the promo could only be shown on TV late at night). Madonna defended the video, saying: “I would like to address the whole issue of censorship on television. Where do we draw the line in general? I draw the line at violence and humiliation and degradation.” Musically, this trip-hop shuffle is hypnotic, electrifying and very, very sexy. In truth, the song said it all and made it to the top of the US charts.

10: GHOSTTOWN (2015)
2015’s Rebel Heart likely won’t go down as Madonna’s favourite album. Persuaded to try writing with many different of-the-moment teams and producers, she found the recording process difficult, and much of the material was then leaked online ahead of its official release. But this second single from the album remains of the best Madonna songs of the 2010s. Created with pop powerhouse Jason Evigan, it’s her most commercial ballad of the decade and would likely have been a global chart-topper just a few years earlier.

9: MUSIC (2000)
French producer Mirwais has been working with Madonna on and off since the turn of the millennium, and this title track from their first studio collaboration was an international No.1. Fusing Madonna’s mainstream pop-dance with cutting-edge European production created a critical and commercial hit that was one of the world’s most successful singles of 2000 and remains her final US Hot 100 chart-topper to date. Ignore the fact that Ali G turns up in the video – people liked that sort of thing back then…

8: TAKE A BOW (1994)
Chart connoisseurs will scratch their head at this statistical anomaly: Madonna’s longest run at the top of the US Hot 100 (seven weeks in 1995) and yet the first Madonna single to miss the UK Top 10 in ten years. What gives? In truth, Madonna’s UK single sales just got lost in the Christmas rush, and the Babyface duet managed a respectable six weeks on the charts. Its status as an AOR classic and that nicely styled video assures Take A Bow’s place among the best Madonna songs, while the storyline for the clip was revisited for another great Madonna ballad, 1995’s You’ll See, created with David Foster.

7: RAY OF LIGHT (1998)
Madonna so definitely nailed this one that people don’t often know it’s a cover song. Lifted from an obscure folk duo’s album from 1971, a demo of the track (then titled Sepheryn) came to Madonna’s attention during the recording sessions with William Orbit. The song morphed into Ray Of Light and hit radio in May 1998 as the parent album’s second single. The electronic techno-riff was a sonic sensation and became the highest-debuting Madonna single to date on Billboard (though it would climb no higher than its opening position of No.5); in the UK, it went all the way to No.2. Ray Of Light’s video was directed by Jonas Åkerlund and placed the singer across a montage of images of daily life playing at super-fast speed. A simple yet supremely effective concept, it became much parodied across popular culture in the years that followed.

6: LIVE TO TELL (1986)
Madonna’s genius for reinvention truly begins here. The frenetic pace of the Like A Virgin whirlwind had finally slowed by the start of 1986, with Dress You Up becoming the album’s final single. After such a phenomenal run, everyone expected more of the same… but this sensitive power ballad, accompanied by Madonna’s stripped-back styling in the obligatory music video (promoting her then husband Sean Penn’s movie At Close Range) was as startling a move as could have been imagined. This first collaboration with Patrick Leonard remains one of the best Madonna songs to come from that partnership, and hit No.1 on the US Hot 100 while also topping the adult contemporary charts, doing much to secure Madonna’s longevity. There were many more surprises to come but, from here on, no one would underestimate her ability to know when to shift direction.

5: BORDERLINE (1984)
This Motown-influenced midtempo classic was the first Madonna song to properly embrace the pop sensibilities that lie at the heart of her appeal. Everything that had come before was unashamedly dance-infused, but Borderline was aimed at the pop stations in America’s heartlands. Its yearning ode to adolescent anxiety did much to cement Madonna’s character in the court of public opinion during those early years, with the Mary Lambert-directed video casting the singer as a street urchin who makes good without forgetting where her true loyalties lay. Of course, the real artist was, arguably, more calculating than that, but therein lies the power of a great song and video. This effortless radio smash sounds as good today as it did in the summer of 1984, when it became Madonna’s first US Top 10 single (in the UK, it would have to wait until reissue in early 1986 to reach similar heights).

4: HUNG UP (2005)
After the folktronica of 2003’s American Life, Madonna returned to a formula that had served her so well on the reinvention that was Ray Of Light. Sourcing another maverick British producer, Stuart Price became Madonna’s William Orbit for the 2000s. Their knowing dancefloor smash Hung Up hit the jackpot by becoming a huge international success, particularly outside the US (it was a UK No.1 for three weeks). After writing to ABBA hitmakers Benny Andersson and Björn Ulvaeus, she secured permission to sample the group’s Gimme! Gimme! Gimme! (A Man After Midnight), thereby elevating the song from great to classic status. Its stellar performance helped launch parent album Confessions On A Dance Floor in spectacular style, while Hung Up immediately staked is claim among the best Madonna songs of the 21st century.

3: VOGUE (1990)
It’s incredible to imagine that this era-defining anthem almost ended up as a throwaway B-side, created because Madonna needed more material to pad out the final single releases from Like A Prayer. Shep Pettibone was a respected remixer who had worked on many of the best Madonna songs of the 80s – including Causing A Commotion and True Blue – and co-wrote Vogue with the singer. This deep-house pop cut was inspired by the “house ball” community and its underground scene, so brilliantly chronicled in the Ryan Murphy TV drama Pose. David Fincher directed the video, while the song became the best-selling single of 1990 and was added to the I’m Breathless soundtrack album, issued that same year to promote Madonna’s role in Dick Tracy. No one remembers that collection much, but everyone can remember trying to copy these iconic dance moves…

2: INTO THE GROOVE (1985)
Much of the world first heard this track during Madonna’s performance at the Philadelphia leg of Live Aid, where her three-song set seemed so thrillingly different to those from the largely old-school rock royalty line-up. You couldn’t escape Madonna in the summer of 1985, and this demo, tidied up for inclusion in the soundtrack of her first major movie, Desperately Seeking Susan, was the Europe-wide smash of that summer, though US chart rules meant it was ineligible for the listings, as the song had been issued a bonus track on the stateside 12” of another Madonna hit, Angel. This urgent synth-dance cut was named Billboard’s dance song of the decade at the end of the 80s.

1: LIKE A PRAYER (1989)
If Madonna could ever really be accused as issuing something as predictable as a premeditated showstopper, this would be it. A luscious gospel-tinged anthem wrapped up in an uplifting pop melody with more than just a nod towards the dancefloor, where – even in 1989 – most would have said Madonna still made her home. Topping our list of the best Madonna songs, this anthem would shatter that musical stereotyping for good. Of course, the controversy wasn’t far behind but, 30 years on, it’s hard to imagine what all the fuss made over the pop promo was about. In an era of Black Lives Matter, Madonna proves – yet again – she’s way ahead of the curve. On radio – then and now – this is simply five minutes of joyful, sonic ecstasy. Madonna revisits this classic whenever she wants us to remember what she’s best at: the perfect pop confection.


https://www.thisisdig.com/feature/best-madonna-songs/