This fall, Madonna will embark on her Rebel Heart tour, covering multiple cities throughout the United States and Canada. In anticipation of the shows, the Spectrum Culture staff selected what we believe to be Madonna’s 10 greatest songs. Enjoy!

10. “Express Yourself

“Come on girls!” The star shouts over the opening beat, “Do you believe in love?” A manifesto of female empowerment, “Express Yourself” solidified Madonna’s image as the priestess of sex-positive feminism. The song was intended as a tribute to Sly and the Family Stone and the funk band’s influence can be heard in the song’s saxophone, percussion and backup chorus. Its use of handclaps and brass instruments set it apart from much of Madonna’s more overtly pop dance numbers. The nod to soul was also in part an effort to expand her audience, reaching beyond the teen appeal. The song was an exuberant reminder to be honest and true to oneself and according to critics, it was revolutionary in1989. Nowadays it goes in one ear out the other, which is all that’s needed from a dancehall classic. Directed by David Fincher, the music video is a must-see. It’s a gender fluid call-to-arms set in Fritz Lang’s Metropolis. Madonna plays an urban demigod, decked in an evening gown and a power suit as she lords over an army of shirtless men. It cost $5 million to make and it remains the third most expensive music video of all time. The song’s lasting influence can be heard in the musical structure of Lady Gaga’s “Born This Way” and, in a touching note of Americana, it was also Kelly Clarkson’s audition song on “American Idol” back in 2002. – Erica Peplin

9. “Justify My Love

Madonna’s reputation for controversy didn’t start with “Justify My Love.” She’d already writhed on the VMA stage in a wedding gown, released a hit single about teenage pregnancy and danced in front of burning crosses in a music video. But no other song in her impressive history of provocation matched the pearl-clutching reaction to “Justify My Love.” MTV banned its arty, black and white video (a clear inspiration for the hotel peekaboo of Beyoncé’s “Haunted”). That clip, directed by Jean-Baptiste Mondino and parodied to perfection with Madonna’s help on SNL, now seems quaint. But it was emblematic of the moral panic she’d fought against thus far. Madonna, always the firebrand, didn’t retreat from the wave of backlash. She rode it. Erotica, and its accompanying coffee-table stunt Sex, soon followed. Their titles alone signaled she wasn’t just flirting with carnal themes.

“Justify My Love” is by a wide margin Madonna’s sexiest song, even if it isn’t overtly dirty on paper. She sing-speaks about kissing, holding hands and running naked in various European capitals. When held side by side with, say, Rihanna’s joyless “S&M,” her lyrics appear a shade edgier than a Hallmark card. Madonna doesn’t have to invoke whips and chains to be dangerous and subversive. Instead she moans and sighs over a slinky trip-hop beat while embraced by a menacing synth drone. Lenny Kravitz, who co-wrote the song, provides ethereal vocal flourishes, which offer a ghostly contrast to the come-hither coos of Madonna’s background singers. “Justify My Love” is the long, deep intake of breath that follows a lover’s first touch. It penetrates with suggestion, seduces with anticipation and thrills without climax. This is sonic foreplay as an end in itself. – Peter Tabakis

8. “Material Girl

The lyrics were an instant mantra. With their synth arrangement and robotic hook, they were as catchy as they were ironic. The robotic vocals and repetition aren’t for everyone but the song reflects an important moment in Madonna’s career and a changing cultural attitude at large. Above all, “Material Girl” expresses a profound truth about Madonna’s postmodern, consumerist image. Like much of Madonna’s art, the music video is referential. Showcasing Madonna’s dancing and acting abilities, it was based on Marilyn Monroe’s performance of “Diamonds are a Girl’s Best Friend” from the 1953 film Gentlemen Prefer Blondes. Her pink dress and pearl necklace remain instantly recognizable. It was on the set of that video in 1984 where Madonna met Sean Penn, her first husband. More importantly, the music video marks a cultural shift in the conception and creation of the “blonde bombshell” celebrity. If Marilyn’s fame was forced upon her, Madonna’s was chosen and “Material Girl” is evidence of the later star’s ambition, independence and knowing irreverence. The “material girl” isn’t the cage it was for Marilyn but rather, she’s just one persona in an arsenal of neo-Barbie vixens. If the song has any drawbacks, it’s the media’s misinterpretation. Accusations of materialism persist and in her biography, Madonna has a good attitude about it: “God forbid irony should be understood. So when I’m ninety, I’ll still be the Material Girl.” – Erica Peplin

7. “Papa Don’t Preach

“Papa Don’t Preach” was always going to get Madonna in trouble; it just wasn’t apparent right away that she knew that. Whether or not it glorifies teen pregnancy, it certainly does not depict it as a terrible thing, and abortion is not an option for Madonna or the character she embodies for four-and-a-half minutes. But Madonna was never the one to bow to progressive feminist leanings. Instead, she preferred to do things her way, and if that meant writing a love song from the point-of-view of an impregnated teenager who is – or at least believed herself to be – in love, the artistic integrity of her vision would not be swayed by any political leanings.

As Madonna manipulated her image more and more in the ensuing decades, all of this has become undeniable in retrospect, but there is a reason the song was a hit back in 1986: It’s a brilliant pop song. The song has classical influences that hint at the increasingly ambitious music Madonna would make later in her career and some of the best dance pop production she had up to that point, and it sets the stage perfectly for the sweet but anthemic, direct, and racy tunes that make up True Blue. With a hooky, catchy chorus that could make listeners everywhere dance and sing to ideas they did not quite agree with, “Papa Don’t Preach” was always going to be a hit — and a lasting one — as well. – Forrest Cardamenis

6. “Like A Virgin

It reflects both on my age and upbringing that my introduction to “Like a Virgin” was the Weird Al parody “Like a Surgeon.” Certainly, my parents probably thought Al’s questionable medical practices would be easier to explain rather than discussing the chorus of one of Madonna’s biggest hits. But, when I finally made my way back to the original, I found a buoyant, bouncy and wonderfully sex-positive smash, which surely was a breath of fresh air during the glam rock dominated ’80s. Hilariously (or sadly), it was Madonna’s forward thinking views on sex that made conservative heads explode, rather than the misogyny of Guns N’ Roses or other hyper-macho rock groups. Funny how things get more controversial when it’s a woman singing about how much she loves sex.

But Madonna didn’t care, she rode the outrage all the way to the bank. “Like a Virgin” became her first number one hit and ushered in an era of pop dominance that few other artists have ever come close to grasping. “Like a Virgin,” even after a few ubiquitous decades in the pop consciousness, is as fresh and catchy as it was from day one. There’s a shimmer to the keyboards and guitars, paired nicely with the Thriller-esque bass line. Then there’s that bridge, erotically charged, of course, but also sparking with beauty. Now, if you’ll excuse me, I need a full day to re-listen to Like a Virgin and Dare to be Stupid in tandem. – Nathan Stevens

5. “Holiday

When “Holiday” was released in September 1983 as a single for Madonna’s eponymous debut album, it was an almost instant critical hit and club favorite. Both the US and the UK ate the song up, and it quickly jumped the charts to become her first hit single, coming in at 88 on the Billboard Hot 100 and reaching #16 in January 1984.

Written by Curtis Hudson and Lisa Stevens of Pure Energy and remixed by DJ John “Jellybean” Benitez, it was originally brought to Madonna by producer Reggie Lucas to round out her forthcoming debut. It was eventually sent to Fred Zarr for his programming and synthesizer genius and to add the famous outro piano solo.

There is possibly no other piece of music that is as infectious as “Holiday.” From the airy synths and the steady electronic beat to the melodic flourishes of the keyboard and Madonna’s enthusiastic vocals, it couldn’t be anymore catchy. It has all the defining qualities of 80s club music, even down to the sort of cheesy music video. But the song has, like Madonna herself, transcended time to become one of the most beloved late-night club favorites. For a track that clocks in at just under seven minutes, it feels like it could go on forever, and everyone would be happier for it. Its genius is in its ability to conjure such a care-free feeling. For this, “Holiday” will forever remain a club favorite and one of Madonna’s greatest tracks. – Nicodemus Nicoludis

4. “Vogue

The cultural reach of Madonna’s 1990 smash, the best-selling single of that year, was so great that even a Falstaffian patriarch from Sweden at my old office was known to suddenly burst out, “Strike the pose.” One of this pop icon’s most iconic recordings is, aptly enough, purely about the superficial. “Vogue” was originally released on I’m Breathless, an album of music inspired by the movie Dick Tracy, a lushly photographed comic strip adaptation that was all style and little substance. It’s a charge frequently leveled at Madonna. But style is her substance, and these soaring synth lines and pulsing beats celebrate her basic M.O.

You can’t talk about this media-savvy star without talking about her music videos, and the stylish black and white video for “Vogue” was directed by none other than David Fincher. Still a few years away from Aliens 3, his inauspicious feature film debut, Fincher won Best Director at the MTV Music Video Awards two years in a row, for “Express Yourself” and this trend setter. With its spoken-word homage to classic movie stars like Garbo and Dietrich, “Vogue” looks backward as it looks forward, a catchy survey of the glamour and celebrity of ‘70s disco and turn of the ‘90s house. It was probably in some way indirectly responsible for Miley Cyrus, but don’t hold that against Madonna.

3. “Borderline

Released as the fifth and final single off her classic, self-titled debut, “Borderline” was and is unlike anything else on the album. Where the preceding singles (“Everybody,” “Burning Up,” “Holiday” and “Lucky Star”) relied heavily on a distinctly electronic, early-‘80s sound and Madonna’s pinched, often childlike vocals, “Borderline”s piano-based arrangement, more mature vocal performance and surprisingly complex chord structure felt somewhat anomalous within the context of the album. Furthermore, while the Madonna album came out in July of 1983, it would be nearly two full years before “Borderline” was released as a single in February of 1984. By this time, she had already released her follow-up smash, Like A Virgin, and was in the process of getting ready to promote that album’s singles.

Within this context of heightened critical and commercial awareness, it’s not surprising the song went on to become her second Top Ten hit. What is surprising, given the strength of the song and its subsequent staying power, is that it took as long as it did to be released as a single. As the second track on the album, “Borderline” follows the similarly successful “Lucky Star,” a Top Ten single also released well after the album’s initial appearance. But there’s something about “Borderline” that makes it unlike nearly anything else in the Madonna catalog.

Fairly straightforward throughout its instrumentally sparse verses, the song begins to grow into something new and different somewhere within the pre-chorus. The chords veer off in unpredictable directions, an added depth accompanying the somewhat atypically thoughtful lyrics. Landing on the triumphant chorus, the piano prominently placed in the mix, “Borderline” suddenly becomes the greatest song Elton John never wrote. With her vocals keening and the piano employing an almost gospel-like progression, it churns out the massive hook for which the song has long been known and loved. Unlike anything else on the album on which it appears, “Borderline” possesses a timeless quality and stands as one of the best pure pop songs the early ’80s, not to mention the entirety of Madonna’s recording career, had to offer. – John Paul

2. “Like A Prayer

In a career full of genre redefining risks, Madonna’s “Like A Prayer” represents a powerful piece of experimentation that paid dividends. It’s arguable that without the eponymous single from her 1989 album, her star might have faded alongside so many other ’80s pop starlets. The song straddles so many divisive lines, not unlike Madge herself. Between piety and sexuality, agency and fealty, she strikes a resonant balance between the chiefly warring sides of her public persona to form the quintessential distillation of what a Madonna song had the potential to be.

On first spin, perhaps the song isn’t that much better than the litany of hits that preceded it, but there’s something about the juxtaposition of pop rock and a more orchestral gospel approach that brings “Prayer” such transcendence. It’s not that lyrics conflating praying to Jesus with sucking his cock are particularly shocking, despite the controversy they stirred at the time. It’s that Madonna evokes such earnest longing in her vocal performance while doing so. Artists like Lady Gaga have followed in her clergy-bait agitprop footsteps, but the essential element missing from such pretenders is always the actual struggle. Sure, lyrically, the song is little more than an expertly evocative marathon of well-timed double entendres, but within that (admittedly infectious) framework, the artist who would later help make Kabbalah a thing in pop culture is going twelve rounds with her own Catholicism.

It’s that urgent sense of conflict that drives “Like A Prayer,” even more than the soaring choral assistance and Mary Lambert’s incendiary Leon-As-Jesus music video accompaniment. It’s a future hall of famer in her prime finding the right thought at the right moment and wrestling it to the ground for our entertainment. – Dominic Griffin

1. “Into the Groove

Madonna has always been an artistic striver. The giddy joys of her early club work soon gave way to increasing thematic and musical complexity. Her ambition (sometimes as a blonde, but not always) climaxed on excellent one-off singles (“Vogue,” “Justify My Love”) and two classic albums (Like a Prayer, Ray of Light). It also resulted in her first true misfire, the wan “electro-folk” of American Life. She redeemed herself, briefly, on the fine Confessions on a Dance Floor. That LP’s lead single “Hung Up” was a concession and also an admission of guilt. Though great at many things, including adult-contemporary balladry, Madonna yet again proved herself unmatched at delivering killer choruses over a breathless beat.

“Into the Groove” is the purest version of melody, melody, melody set to a metronomic pulse. What was once dismissed as simplistic — Madonna herself has called the single “dorky” — has since entered the pop pantheon. “Into the Groove,” so effortless and buoyant, succeeds because it offers no grand statement. It begins in the middle of an argument, with Madonna’s final, most persuasive reason to join her under a disco ball (“…And you can dance!”). Movement turns into an extended metaphor for romance and, of course, sex. But dance is also an expression of self-love (“Only when I’m dancing can I feel this free/ At night I lock the doors, where no one else can see”).

Over the years Madonna has dressed “Into the Groove” up with various remixes (see You Can Dance and The Immaculate Collection). Except, extended interludes and distracting percussive elements only muddy its fundamental elegance. Which means the essential cut of “Into the Groove” was recorded for Desperately Seeking Susan. Wouldn’t you know it? It’s a narrative we’ve become familiar with: Madonna, at her best and worst at once. – Peter Tabakis

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