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14. ‘Hard Candy’ (2008)

Pugilism and peppermints, anyone? While the theme of “sweet but tough” made for a compelling album, the cover art didn’t quite land. This snap of Madonna looks more like an outtake than a photo shoot’s best take and superimposing it over a close-up of a mint looks a bit PhotoShop 101. Hey, they can’t all be winners.

13. ‘American Life’ (2003)

Che Guevara’s visage has been co-opted so often and for so long it’s almost pointless to gripe about it, but there’s something particularly odd about Madonna casting herself in the image of the Marxist revolutionary. Guevara was a guy who hated capitalism so much that after helping facilitate the Cuban Missile Crisis, he urged Russia to launch those atomic warheads on U.S. citizens, arguing that it would be worth killing “millions” of innocents just to deal a blow against American imperialism.

Now, Madonna is certainly revolutionary, but she’s also a dyed-in-the-wool capitalist. Hell, she didn’t navigate her way from broke beginnings in New York City to conquering the globe and making millions of dollars by following the Communist Manifesto. The connection between the two, on an album cover no less, is just a bit rich.  

12. ‘Madame X’ (2019)

With those pencil-thin eyebrows, piercing blue eyes and blazing red lips (Taylor could never) stitched shut, Madonna announced her Madame X era with a striking image. It is among her most iconic? Probably not, but the Queen of Pop has accumulated a rich library of culturally significant images over the course of four decades, so the fact that this magnificent image isn’t even in her top 10 is still a testament to her keen eye.

11. ‘Music’ (2000)

Two decades before Cowboy Carter, Madonna cosplayed cowgirl with her 2000 classic Music. M’s blonde locks spill out from beneath her baby blue Stetson, which is a few shades lighter than the sumptuous navy blue of her outfit, as she poses in front of classic Americana cars. Her defiant look has a love me or leave me quality, and based on the response to Music, audiences resounding went with the former.

10. ‘Bedtime Stories’ (1994)

A soft, sensuous image of the Queen of Pop in bed rocking a lace nightgown (and nose stud) accompanied the lush Bedtime Stories album. Unlike a lot of art pieces featuring women reclining in bed, this one finds the subject staring directly back at the camera, challenging the male gaze while simultaneously inviting it. Look quick and you might not even think it’s Madonna, mistaking her for one of the Golden Era Hollywood stars she took inspiration from, such as Jean Harlow.

9. ‘Rebel Heart’ (2015)

There’s something quintessentially Madonna about the cover to Rebel Heart. We see the Queen of Pop from the bare shoulders up, staring upward with her mouth open slightly as if to say something. Her hair is perfect, the makeup is immaculate – it could be a simple glamour shot if not for the black cord tightly woven around her face, pushing her skin around and contorting her iconic image. Weird and lovely.

8. ‘MDNA’ (2012)

Like her next album, Rebel Heart, the cover to MDNA could have been a straightforward, flattering image of the Queen. She’s in a fabulous shade of rose-red, rocking a choker, fingerless velvety gloves and a cinched waist. But Madonna was never content to merely be beautiful, and so the image is given a twist, with vertical lines chopping up the vivid photo and giving it a disjointed quality, almost as if you’re looking at her through a crystal tumbler.

7. ‘Erotica’ (1992)

For Erotica, Madonna took pop to lascivious heights and tantalizing depths no star had dared to explore before. To that end, the cover art tracks like a Warholian version of smut, looking more like a poster you’d see around Times Square in the seedy ‘70s than at a Sam Goody at your local mall. Eyes closed, mouth open and awash in a blinding white light, Madonna made it clear that his album was not for the faint of heart.

6. ‘Ray of Light’ (1998)

A visual 180 when compared to Erotica, the cover to Ray of Light shows Madonna in her electronic earth mother era, straddling the line between maternal respectability and techno club futurism. The aquamarine hues of the background and her outfit give everything a familiar yet foreign feeling, almost as if you’re peeking into a strange, undersea world – it’s of this earth, but not the kind of thing you’re used to seeing every day.

5. ‘Like a Prayer’ (1989)

It’s ironic, or perhaps fitting, that Madonna’s most lyrically candid album is the only one that doesn’t feature her face on the cover. Instead, we get a close-up of her bejeweled hands resting on her unbuttoned jeans with a beaded pendant dangling in front of her bare midriff. It’s more religious than raunchy, but even so, that didn’t stop L7s from clutching their pearls and crossing themselves defensively at the time.

4. ‘Confessions on a Dance Floor’ (2005)

With her face turned away from the viewer, back arched and limbs splaying in four different directions, Madonna strikes a pose for the cover of this 2005 album, albeit an unusual one. Her hair, a flaming hue of Rite Hayworth red, picks up where the hot pink of her leotard leaves off, giving the entire disco-fied image a sense of vibrancy and motion.

3. ‘True Blue’ (1986)

Herb Ritts (who also did the Like a Prayer cover) shot the photo that covered Madonna’s third album, True Blue. With her skin bleached and platinum blonde hair looking equally pale, this iconic image of Madonna in profile became one of the defining images of the ‘80s. Even with her eyes closed, she’s strong, defiant and energetic. This is a snapshot of a cultural juggernaut coming into her global power.

2. ‘Like a Virgin’ (1984)

Pop iconography doesn’t get much more iconic than this. Wearing a fishnet wedding dress, “boy toy” belt and a facial expression that lets you know the words “like a” on this album cover are key to understanding it, Madonna buried the idea of a blushing bride with this brazen album cover. Despite her name, she’s neither Madonna nor whore in this photo, but a new archetype that she helped forge in the cultural consciousness: An unapologetic, sexually mature woman who’s pushing boundaries — not for your fantasy fulfilment but for her own empowerment.

1. ‘Madonna’ (1983)

Defiant, hungry and for the first and only time in her career, even a touch naïve, this striking image of Madonna Ciccone introduced the burgeoning pop star to the world. From her bleached hair to the chain around her neck to the cornucopia of bands wrapped around her wrists, Madonna gave ’80s teens a look that had seismic repercussions across shopping malls from Jersey to SoCal. Cradling her face, tugging on the chain around her neck and staring directly into your eyes, Madonna seems to be conveying a lot with this image – namely, the message that she had arrived, and she was here to stay.