The 50 Greatest Madonna Songs

To honor the release of Madonna’s brand new Rebel Heart album, I thought it would be a good idea to take a look back at her greatest works. As a sister list to The 50 Greatest Michael Jackson Songs, this list counts down the Queen of Pop’s best songs through all of her many reinventions, bold statements, beautiful messages, and euphoric dance numbers. Here’s hoping that time will add a few cuts from Rebel Heart to this very list! Without further adu, I present to you the 50 Greatest Madonna Songs.

50. Miles Away

50. Miles AwayMadonna’s 2008 album Hard Candy was a rare misstep for Madonna, on the whole, but there were enough worthwhile moments to make it a passable record. None of said moments were as great as “Miles Away,” a mid tempo ballad swirling with acoustic guitar and a looped hip hop-lite beat. The presence of Timbaland and Justin Timberlake is instantaneously apparent, but it all fits together a little more organically than some of their other collaborations. Madonna, who was approaching the end of her marriage, exemplified an earnest side of herself that always seems to engage us just as much, if not more, than some of her most boundary-pushing works.

49. Love Tried To Welcome Me

49. Love Tried To Welcome Me

At large Bedtime Stories is the most soulful record in Madonna’s catalog, and she really made it work. Despite never being released as a single or even finding its way into a concert setlist, “Love Tried To Welcome Me” is an incredible standout on the record. The sultry track is one of her velvetiest, swirling with strings and light touches of acoustic guitar, but her vocals provide the biggest atmospheric texture. Whereas many other artists would have over-sung it, her restraint is admirable, and, no, it doesn’t come across as lack of ability. “Love Tried To Welcome Me” feels like being cuddled up with a nice glass of wine, and Madonna really milks it as much as she can.

48. Sorry

48. SorryMadonna has many landmark singles in her career that have always seemed impossible to follow up, and “Hung Up” is easily one of those tracks. However, she really knows how to throw a damn good one-two punch. “Sorry,” the second single lifted from Confessions On A Dance Floor, is a particularly compelling dance pop number that harks back to ’80s electro, with a modern twist, of course. It’s heavy, almost menacing bass line controls the mood here, and provides the perfect backing for Madge’s commanding lyrics, but the song never strays from its main focus: being a dance song. “Sorry” really succeeds on all fronts, and it still feels as fresh as it did a decade ago.

47. Beautiful Stranger

47. Beautiful StrangerIt’s a bit strange to say that Madonna’s contribution to the Austin Powers: The Spy Who Shagged Me soundtrack is such an incredible song. “Beautiful Stranger” sees Madge tackle psychedelica in an authentic, almost straightforward way, but she still managed to crank it up a notch and present something completely contemporary and electronic-driven. In addition to its unique groove, the track is one of the catchiest tunes in her entire catalog, almost to a fault. This is a true representation of Madonna throwing a bunch of things on a plate that should never work and giving us something not only palatable, but actually addictive. This is the magic of Madonna.

46. Let It Will Be

46. Let It Will Be

Madonna has never been fearful of self-evaluation in her music, but never has it come across as quite this euphoric. “Let It Will Be,” despite never getting a chance to dazzle on radio, is a true stand out on Confessions On A Dance Floor. The track is quite simple in nature, essentially looping a sublime synthesized orchestral hook that holds our attention in a way that doesn’t require the intricate structuring of the other tracks on the record. When you throw in some of the reflective lyrics dance pop has ever heard  and one of the greatest climaxes in her entire catalog, “Let It Will Be” is really nothing but absolute perfection.

45. Lucky Star

45. Lucky StarFrom an image standpoint, “Lucky Star” is the inception of “Madonna the Fashion Icon.” Musically, this is the beginning of “Madonna the Pop Star.” Her second real hit, penned entirely by Madge herself, is a bubbly, somewhat naive track with that ’80s charm she almost singlehandedly invented. It still feels like a precursor to her more daring works to come, but “Lucky Star” is really Madonna at her most “boiled down to basics.” Had she not gone on to become the undeniable Queen of Pop, this track could have been all but forgotten, but it stands out as a track that helped put her on the path to becoming one of the most game changing artists in the history of the world.

44. Something To Remember

44. Something To RememberThe soundtrack to the film Dick Tracy (co-starring Madonna, naturally,) entitled I’m Breathless, isn’t one of her most remembered or lauded works; it’s not even really considered one of her studio albums. Even despite spawning a pair of big hit singles (“Hanky Panky,” and…oh yeah… “Vogue,”) its jazz and swing direction was cute at best. However, it’s focal-point ballad, “Something To Remember” is a stunningly gorgeous moment that really stands out. The track has a timelessness about that it allowed it to fit in the context of the album (unlike “Vogue,”) and still feel like a contemporary piece. When it became the title track to her collection of ballads 5 years later, it still sounded as fresh as it originally did.

43. Love Profusion

43. Love ProfusionThe American Life album isn’t Madonna at her best, coming across more as a Music rehash than an actual advancement in her sound. Still, there were some great moments tacked in there, “Love Profusion” being the clear stand out. This folksy electro pseudo-ballad showcases a rare vulnerability for Madonna… a Madonna in love. The track comes across as beautiful even through a couple of clichés and dodgy lyrics here and there, and still manages to feel like an intriguing pop song. What makes the song a triumph isn’t that it’s a diamond in a rough of an album, but rather its soulfulness and ability to take otherwise boring components and make them feel rather gorgeous all together.

42. La Isla Bonita

42. La Isla BonitaIt goes without saying that “La Isla Bonita” is one of Madonna’s most enduring hits. This Latin infused pop classic, the last single lifted from her hit-heavy True Blue LP, showcased a more adult contemporary side of of her that still managed to have the flair of intuition of her other classic pop gems. While, on the whole, “La Isla Bonita” doesn’t have the spark of “Open Your Heart” or the edge of “Papa Don’t Preach,” the track has endured the test of time far better than its sister tracks, and even Madonna has never really been able to escape including it in her concert setlists. If you put this song on today, it’s still going to get a great response, and that’s a true testament to its charisma.

41. Burning Up

41. Burning UpIt’s hard to remember a time in Madonna’s career when she wasn’t a household name, wasn’t pushing boundaries in pop music, and didn’t even have a hit to stand on, but there was indeed a time (granted a brief one.) “Burning Up,” her second ever single, is a real stand out for reasons quite contrary to the ones that put her classics on a pedestal. It has a rawness about it that was never going to fuel the same fire that songs like “Holiday,” “Lucky Star,” and “Borderline” would, but, in hindsight, there’s a self-assured hunger packed in there that showcases her innate confidence. Still, it’s rock-tinged bounce is endearing and the hook is deliriously catchy, making for one hell of a great pop song.

40. This Used To Be My Playground

40. This Used To Be My PlaygroundIn hindsight, “This Used To Be My Playground” is the calm before the storm. Just before we were introduced to the full wrath of “Sex Madonna,” she released one of her most tender ballads to date. The track, lifted from the film A League Of Their Own, in which she co-starred, is the first in a decade-long streak of ballads and mid-tempo songs, and although it doesn’t have the edge, bewilderment, or even vocal prowess of many of the tracks to come, it stands out as one of the most emotionally in-tune and chill-inducing. It’s a particular shame that, even though the song made it all the way to #1 in US, it has seemingly gotten lost in the sands of time and is more of a hidden gem now than anything.

39. Get Together

39. Get Together

Confessions On A Dance Floor is a record ingeniously full of reference and influence all strung together in a non-stop stream of electroeuphoria, and “Get Together” is one of its greatest moments. The track is somewhat straightforward in nature, but it has an air of beauty that heightens the experience. Clearly cut from a cloth (maybe even directly) laid out by “Music Sounds Better With You,” the track moves along quite fluidly and doesn’t rely on too many tricks to sound interesting, and as a result, by the time the song reaches its heralding climax, the pay off is that much bigger. Don’t let its “less is more” mentality fool you, though; this is an intricate slice of dance pop heaven.

38. You Must Love Me

38. You Must Love MeCasting Madonna as Eva Perón, not only a legendary historical figure, but one of Broadway’s most iconic roles, in the film version of Evita was quite a bold move on many levels, but fearlessly she tackled the role. While her performance is still considered polarizing, she still found a way to make an impact. “You Must Love Me,” a new track written and recorded specifically for the film, is one of Madge’s greatest performances on record. The simple track has very little instrumentation, which provides the perfect bed for Madonna’s controlled vocals to gingerly rest upon. Her awareness and emotion is truly at its peak, providing a necessary contrast to her many dance pop hits and over-the-top ballads.

37. Gang Bang

37. Gang BangMadonna’s 2012 MDNA album was largely a disappointment, but there was one highlight so incredible that it almost made up for it. “Gang Bang” is about as angry and possessed as Madge has ever been, exhibiting a charismatic violence that immediately drew comparisons to Quentin Tarantino films. The track is rather simple in structure, which a circular quality about that allows for the rawness to resonate. It’s easily one of her most provocative pieces, but in a way she had really yet to exemplify; it’s almost uncomfortably edgy, but she makes it work. By the time “Gang Bang” hits is climax of Madonna screaming, “Drive bitch!,” we’re almost too busy dancing to care.

36. Die Another Day

36. Die Another DayMadonna heading up a Bond Theme makes just a little too much sense. Leave it to her, though, to really make something this interesting. While most theme songs to the various James Bond films have been some combination of over-the-top theatrics and pop fodder (neither of which are particularly bad,) “Die Another Day” is a peculiar electronic cocktail (shaken, not stirred) bordering on cacophony. Miraculously, it somehow is all woven together into a structured pop song, albeit an unconventional one. The track is as boundary-pushing and imaginative as Madonna has ever been, and for something this frightening to actually end up being so addicting really solidifies her genius as an artist and her impact as a pop star.

35. I’ll Remember

35. I'll Remember“I’ll Remember” was a much needed moment of clarity for Madonna. At a time when everything she did was highly controversial, this track reminded us that the music was an important aspect to her art. This light and non-threatening ballad doesn’t use any real pop tricks that Madonna constantly reminds us she has a sleeve full of, but it’s actually successful because of it. The chorus isn’t as grand as it could be, and the lyrics are simple and sweet, but the overall effect of the track is still rather touching, and particularly catchy. “I’ll Remember” is a perfect example of how Madonna has always been more than just one kind of artist at any given time, and it’s really quite beautiful.

34. Material Girl

34. Material GirlIt probably wasn’t her honorary title of choice, but before Madonna was crowned the Queen of Pop, she was widely regarded as the “Material Girl.” As one of her signature tunes, the track is a bubbly ’80s dance pop number with a bouncy bass line and ingenious layering of male backing vocals that sees Madge adopt a tongue-in-cheek persona as a materialistic diva. Maybe the joke was lost on the public, but the track itself is an absolutely iconic snapshot in ’80s pop culture that solidified Madonna’s presence as a tour de force with a drive powerful enough to plow through any amount of criticism or skepticism. The track hasn’t necessarily aged well, but, even today, it feels undeniably fun.

33. Cherish

33. Cherish

“Cherish” is a song that should never have worked. Tacked right in the middle of the otherwise forward-thinking Like A Prayer album, the track is a bubbly pop tune that could have crossed over into deliriously candy coated with just the slightest misplacement. However, Madonna manages to hold it together and “Cherish” holds its place as one of, if not the sweetest fixtures in her envious cannon of hits. From its girl group-esque vocal arrangement, especially its climactic round of parts, to the bouncy bass line, this song is a true pop classic that provided a much needed “soft” yin to her, at the time, highly controversial yang. It’s still one of her most beloved classics.

32. Impressive Instant

32. Impressive InstantThe Music album is a compact whirlwind of controlled chaos that stretches and compresses the boundaries between electronic and acoustic, and it somehow works. One of the record’s biggest attention getters comes in the form of “Impressive Instant,” a straight up electro-throb that thrives on restraint. The song has as much vigor as it does lightness, and somewhere in the middle sits Madonna’s effect-ridden vocals to hold together the otherwise loose structure. “Impressive Instant” feels like a refreshing update on the pensiveness and inner-acceptance from her Ray Of Light album while still declaring a (routine) new state of self, and the track, even today, still feels compelling.

31. Dress You Up

31. Dress You UpBy the time “Dress You Up” was released, Madonna had hit her stride as an unstoppable tour de force on the charts. Despite failing to live up to the cultural significance of many of its surrounding singles (“Like A Virgin,” “Material Girl,” “Into The Groove,”) the track is actually one of her brightest ’80s gems. This is a far more intricate pop song than it seems on the surface, with its stunningly euphoric chorus,  tinges of guitar, thundering percussion, and slightly edgy lyrics (absolutely tame by Madonna standards.) It’s no wonder that “Dress You Up” is such an enduring hit that’s often referenced when talking about the Queen of Pop at the inception of her unwavering reign.

30. Nothing Really Matters

30. Nothing Really MattersMotherhood, or at least a newfound outlook on life because of it, was one of the most present motifs on the impeccable Ray Of Light album. “Nothing Really Matters” is possibly the most vital puzzle pieces to the record as a result. The track is one of the most straightforward dance tracks on the record, intricately nuanced with with piano and backing vocals to soften the frenzy and give Madonna the perfect space to run free with some of her sweetest, most self-aware lyrics to date. “Nothing Really Matters” is Madonna at her most intuitive and liberating, not because of sexual content or empowerment, but because of her aptness to showcase a softer side without sacrificing her integrity.

29. Deeper and Deeper

29. Deeper and Deeper“Deeper and Deeper” sticks out as a rare dance floor filler in Madonna’s ’90s catalog, but it nourishes in such a way that doesn’t leave us really minding. The Erotica single harks back to “Vogue” (even getting a pretty direct lyrical lift,) but gives the sound a much needed makeover. The track is far more an update on classic disco than a proper throwback, and the slightest touch of flamenco gives that little push towards uniqueness that makes this stick as not “just another dance pop song.” “Deeper and Deeper” is a prime example of just how Madonna has been able to contort and adapt various genres to fit her mold, as opposed to the other way around, and an otherwise simple song becomes a masterpiece.

28. Paradise (Not For Me)

28. Paradise (Not For Me)All in all, Madonna’s Music album was a pretty weird project. She audaciously took polarizing concepts and jaggedly exposed their contrasts while making it feel oddly cohesive, and nothing was more successful than “Paradise.” The track is a 6 and a half minute electronic landscape that’s biggest triumph is its subtly. Madonna’s throws out every trick in the book from spoken verses to a French translation to a buffet of manipulated vocals that all somehow navigates us through an unsettling forrest of calming orchestral sounds and grimy synthesizers. There’s not a second on “Paradise” that doesn’t feel vital and intentional, even despite its repetitiveness, and the end result is hypnotically beautiful.

27. You’ll See

27. You'll SeeMadonna’s ’90s ballad binge really climaxed (but didn’t end) with a collection entitled Something To Remember that compiled hits, album tracks, and new recordings that showcased a necessary juxtaposition to her dance floor classics. The project’s lead single “You’ll See” could have been a contrived rehash of some of her better moments, but instead sat comfortably alongside them, and came damn near close to eclipsing many of them. The track is Latin-tinged with a pure, modern production that provides the perfect landscape for a powerfully earnest vocal delivery. Not only is this Madonna at her most exposed but empowered, but this is Madonna at her most beguiling.

26. Oh Father

26. Oh Father

“Oh Father” was one of first times Madonna used her music to allow us a glimpse at her personal life. The devastatingly emotional ballad is a clear strand out from her iconic Like A Prayer album, and despite not living up to the success of the other singles lifted from the project, it has remained a noteworthy moment in her catalog. Even though Madonna’s lyrics paint a complicated picture of her relationship with her father, she never indulges us in anything blatant. At a time when the Queen of Pop seemed like a fearless warrior, “Oh Father” shattered any illusions that she wasn’t as emotionally complex and confused as any other human, and her vulnerability birthed an amazing song.

25. Open Your Heart

25. Open Your HeartMadonna’s True Blue was really the peak of her unparalleled success as a singles act in the 1980s. Before she was really experimenting and really pushing boundaries, Madonna was simply the most compelling pop star in the entire world. “Open Your Heart,” as a stand alone, might just be that singular “peak” moment. The track is musically a step forward from her Like A Virgin singles, but still lacks a believable harmlessness that leaves us digging for something sinister and edgy tucked in there somewhere. This is Madonna at her catchiest, at her most confident, and at her most relatable. There’s something to be said for her uncanny ability to make a damn good, straightforward pop song.

24. Bedtime Story

24. Bedtime StoryMadonna and Björk doesn’t sound like it would ever work, but the Queen of Pop fearlessly tackles “Bedtime Story,” penned by the Icelandic superstar, head on. There is nothing in Madonna’s catalog quite like this, but she owns it and while we’re still left bewildered (as you would with any Björk song,) it actually makes sense. In fact, it even manages to make sense as the title track on a record that is almost entirely saturated with R&B tinged pop songs, most of which are ballads or mid-tempo tracks. Whether her decision to release it as a single was a bid for artistic respect, or a straight up act of fearlessness, the song stands out as one of the finest moments of her ’90s catalog.

23. The Power Of Goodbye

22. The Power Of Goodbye“The Power Of Goodbye,” along with much of the Ray Of Light album, was a track that eliminated this dichotomy between “Mature Madonna” and “Relevant Madonna.” This electro ballad is pretty straightforward from a songwriting perspective, but the production on it endears it to the modern listener that maybe was no longer interested in her ballads from the earlier parts of the decade; she passes that test with flying colors. “The Power Of Goodbye” is a particularly stunning song largely in part to her intricate and poignant lyrics that snap into the melody like a perfect fit. Again, the vocal and musical restraint seem intentional and she uses it to let the emotion come piercing through.

22. Sky Fits Heaven

23. Sky Fits HeavenIn many ways “Sky Fits Heaven” is the definitive track for her Ray Of Light sound. The electro pop song has a number of twists and turns that take us on a musical journey, seemingly through her mind and soul. The lyrics are some of her most poetic and thoughtful, but they move so seamlessly through the changing instrumentation that it’s almost easy to stop comprehending and instead absorb them through some weird musical hypnosis. Even in today’s world, it’s far too ambitious a dance track to ever work in a club setting, but its pensiveness makes up for that. This is Madonna at the peak of her artistry, and she didn’t have to abandon pop music to do it; she just flipped it on its head.

21. Rain

21. RainMadonna’s Erotica album was pretty obviously laced with sexual innuendo, and a great deal of sexual content that was pretty in your face, but “Rain” has always stuck out from the pack. This romantic ballad with trip hop undertones acts as the perfect lyrical foil to the rest of the record, but keeps consistent with the sound she was hoping to achieve; it kind of cuts through the tension she was intent on creating, which almost adds more merit to it. Nonetheless, “Rain” is a stunningly beautiful track that sparkles through many layers and twists without ever crossing over into excess. This was also a great example of her vocal ability at a time when that was the furthest thing from anyone’s mind.

20. Human Nature

20. Human NatureMadonna wouldn’t be the Queen of Pop had she not been so determined to push boundaries in both music and pop culture. There’s always been erotic qualities to her art, but after years of pissing people off and making headlines, she finally took the opportunity to do the polar opposite of apologize in her classic, “Human Nature.” Not only is the closest she has ever come to authentic hip hop, but the sarcastic lyrics and memorable melodies make for a true standout in her discography. Oddly enough, it seemed to be the grand finale, at large, to the “Sex Madonna” era, and there was truly no better message to go out with. This will forever be a defining mantra for her.

19. Into The Groove

19. Into The GrooveIf there’s one side of Madonna we can all agree she holds the crown for, it’s dance pop. When it comes to her ’80s dance numbers, none are more successful than “Into The Groove.” While the sound is textbook and clearly a snapshot in time, there is something so timeless about it that would seemingly still fill dance floors all over the world today, even amongst modern DJ sets. It’s one of her most recognized songs the world over, and one of her most enduring classics. It goes without saying that “Into The Groove” is not only one of the greatest dance pop tracks in her catalog, but one of the greatest dance pop tracks of all time. No matter where you are when it comes on, you’ll be moving.

18. Take A Bow

18. Take A BowThe 1990s were a decade largely saturated with ballads and sultry mid-tempo jams for the Queen of Pop, many of which highlighted her range as an artist talents as a vocalist. There were so many highlights from this era, but “Take A Bow,” the second single lifted from her Bedtime Stories album really stands out. It’s probably the most straightforward of all such ballads, but unlike some of its peers, Madonna chose to keep this one musically and vocally low-key. This is fragile as her voice as ever been, gently laid on top a melancholy array of strings and piano with touches of backing vocals used to present at least some dynamic variance. However, “boring” is a word that strikingly never comes up.

17. Hung Up

17. Hung UpABBA samples are kind of a forbidden fruit, but Madonna was one of the elite few given access to take a bite. “Hung Up” is a soaring success because it lays the groundwork for the concept of her Confessions On A Dance Floor album while simultaneously being completely respectful to the “Gimme! Gimme! Gimme!” sample she was gifted. Still, the track reads like a fresh, new moment in dance pop history, even despite all of its borrowed elements, including lyrics from her own “Love Song.” This reinvention for Madonna, once again, conquered the hearts of pop lovers everywhere, but she had us dancing our hearts out with quite possibly her most club-ready anthem ever.

16. Don’t Tell Me

16. Don't Tell MeAfter throwing on the cowgirl hat and recreating modern disco, Madonna advanced her “Electro Cowgirl” reinvention to the brink of its worth. “Don’t Tell Me” is a stunning track on all accounts for just that reason. Largely a country ballad, she approaches it as if it were an electro anthem; the juxtaposition is shockingly impeccable. For such as simple song, this is truly one of the most intricately produced tracks in her catalog. Through all of its stops-and-gos, glitches, and effects, Madonna makes sure to keep the integrity of the track alive. Not only are her vocals sublime, but the multi-layed effect that doesn’t quite line up perfectly drives the raw emotion of her delivery.

15. Live To Tell

15. Live To TellBy this point in her career, Madonna didn’t have many ballads to balance out her dance floor-filling mega hits, but “Like To Tell” came right on queue. The lead single from her unstoppable True Blue album, even today, remains one of her most crucial hits. The track is a searing pop ballad that still  holds lyrical relevance and is regarded as one of her greatest singles. This was the first time Madge stepped away from the controversy and the ballsiness and gave the world something to really admire. Little did we know, she was only giving us a quick breath before erupting into something bigger and more powerful than anyone could have ever imagined.

14. Like A Virgin

14. Like A VirginWhen you talk about “Classic Madonna,” this is going to be the first track on your mind. “Like A Virgin” was the Queen of Pop’s first defining moment in pop culture. Aside from the iconic video, the iconic VMA performance, and pretty much the fact that it made the entire world realize that she wasn’t a fluke, the track is an impeccable slice of pop heaven. That baseline, that chord progression, that infectious chorus… it’s one those cosmic moments. In a sense, it almost seems like a separate entity from the artist herself, but even Madge hasn’t been able to walk away from her defining early-80s hit, even despite twisting and turning it every which way over the years.

13. Secret

13. SecretAfter Madonna spent most of the early parts of the decade doing her best to ignite a sexual revolution, it was a refreshing change of pace when she kicked off her Bedtime Stories project with “Secret.” This soulful, acoustically driven ballad feels far more thoughtful and organic than many of her previous works, and even much of her work to follow. The track has a sleek arrangement that gracefully glides from section to section, but never feels boring or contrived. The more you listen to “Secret,” the more elegant and beautiful it becomes, and even 20 years later, feels just as fresh, as relevant, and as important as it did then. It showcases as side of Madonna that is undeniably mature, well-rounded, and talented.

12. Music

12. MusicKicking off her third decade as the undisputed Queen of Pop, Madonna, once again, shook things up with a new persona, “Electro Cowgirl Madonna.” While nothing about this should have worked, within the first few bars of the title track to her Music LP, it’s clear that she knew exactly what she was doing. This modern disco anthem is riddled with manipulated vocals and intricate grooves, but what pierces through it all is an undeniably catchy melody and a carefree message that harks back to her very first single, “Everybody.” Despite sounding unlike anything else on the radio, it sucked us all in the way only Madonna could get away with, and years later is still being referenced in modern pop.

11. Papa Don’t Preach

11. Papa Don't PreachFor all of Madonna’s ballsy moments, “Papa Don’t Preach,” relatively speaking, might just be her ballsiest. Fearlessly taking on the at-the-time taboo subject of teenage pregnancy, the Queen of Pop managed to piss everyone off enough to land herself one of the biggest hits of her career. Culturally speaking, this one of her most important moments, but musically speaking, it’s just as exceptional. It follows a pattern and structure that has proven successful for years, but with its string arrangement, anthemic chorus, and dancy production, this is just the kind of pop masterpiece that gets cemented into history. Once again, this is a direct, audible example of Madonna’s impact on pop culture and pop music.

10. Erotica

10. EroticaIn many ways, the title track to her fifth studio album could have instantly been written off. It could have been considered too similar to her previous hit, “Justify My Love,” or a desperate attempt to shock the public, but instead, “Erotica” is truly one of her greatest achievements. With its spoken verses and hypnotic chorus, the song reads far more sultry than it does explicit,  but somehow makes sense in the pop realm. Madonna, again, showcases a side of herself that she’s had been clearly itching to unleash, and, in turn, made a statement about censorship and artistic integrity, but still managed to produce an absolutely fantastic track that sticks out as one of her most relevant and important.

09. Express Yourself

09. Express Yourself

“Express Yourself” is the quintessential “Feminist Madonna” anthem, but it also remains one of her most enduring mega hits. What makes it such a great track is her ability to inject a commanding, almost soulfulness into her delivery that establishes her authority. Following up the cultural phenomenon that was “Like A Prayer” would be an otherwise impossible feat, but Madge had more than just a couple tricks up her sleeves. When you throw in some brass, a funky bass line, a Staple Singers interpolation, and a chorus as euphoric as pop music has ever known, it’s easy to see why “Express Yourself” is one of her most referenced, recognized, and respected hits.

08. Ray Of Light

08. Ray Of LightMadonna’s Ray Of Light album is widely considered her magnum opus. There are so many tracks on that record that are worth noting, but there’s something particularly special about the title track. For one, it’s the most dancy, the most pop, and the most commercial on the record, but its almost one of her ballsiest. This club-ready anthem is a euphoric, liberating song that, once again, made Madonna the coolest pop star on planet earth. There’s a sincerity garnished throughout “Ray Of Light” that highlights its intricacies, allowing the song to feel as serious as any alternative rock songs captivating critics’ attention at the time, and in fact, made the Queen of Pop feel like a proper rock star in her own right.

07. Borderline

07. BorderlineAfter the public finally welcomed Madonna into their good graces with the all-in-all harmlessness of “Holiday” and “Lucky Star,” she found the time to sucker punch us with one of the ’80s most important pop songs. “Borderline” truly upped the ante for Madge, not only with its memorable video, but its subtly unique structure and her most intricate chorus to date. Even today, the song resonates as a classic ’80s pop number that holds up flawlessly against some of her biggest, brightest hits. Not to mention, this was the moment where you had to start taking Madonna seriously as a driving force in pop music and not just write her off as a fleeting moment in a revolving door genre.

06. Drowned World/Substitute For Love

06. Drowned World“Drowned World/Substitute For Love” is a song that remains one of her greatest moments simply based on musical merit. Hardly one of her biggest commercial hits, the track is widely regarded as one of her most beautiful, most honest, and most poignant. Within the first few notes, it’s immediately clear that this is a different Madonna from any of the ones we thought we knew before. There’s a self-awareness and timidness that bares a stark contrast to the fearlessness we had become accustomed to, but it somehow doesn’t feel out of character. “Drowned World” exposes her vulnerabilities as a human, but her talent as a vocalist and as an artist, and it remains one of the brightest gems in her catalog.

05. Justify My Love

05. Justify My LoveAlready a provocative artist, she really “went there” upon the release of “Justify My Love.” This is another track that really became overshadowed by its music video, but you have to really appreciate the musical accomplishments of the song itself. The almost entirely spoken, R&B-tinged track comes across more as an art piece than a pop song, but leave it to Madonna to send it to the top of the charts. It ushered in a new era for the artist that was far more sexually explorative, if not down right explicit, but also far more experimental and mature when it came to her music. “Justify My Love” is a landmark moment in a career jam-packed with landmark moments, and even today, manages to sound as fresh as ever.

04. Holiday

04. HolidayThis was the track that properly introduced the world to Madonna. Looking back, on paper, the track is hardly her biggest international smash, but it has endured the test of time and has remained one of her most memorable, important works. The uplifting dance number is a blueprint for the classic “Madonna sound” that has evolved and changed countless times over the years. There is something so magical and endearing about it, even despite its simplicity, that still exemplifies how no one could ignore this artist. Between its delirious, funky bass, heralding synth chords, and crowd-friendly hook, this irresistible tune became the big bang for the most compelling pop star in the history of the genre.

03. Vogue

03. VogueIn many ways, “Vogue” is Madonna’s greatest contribution to pop culture. Outside of the memorable video and the highly referenced dance craze it catalyzed, the song itself is a unique slice of dance pop heaven. Compared to what the genre has become, “Vogue” is a highly restrained, tactful track composed of simple parts layered on top of each other to create something rather striking. Instead of being a mindless, predictable piece, this is a song that’s actually equally as interesting to listen to as it is to dance to. “Vogue” isn’t exactly Mozart, but it is a monumental landmark for a monumental artist, and that’s worth celebrating. Not to mention, it’s the only time she’s evergotten away with rapping.

02. Frozen

02. Frozen

In hindsight, Madonna’s biggest asset has been keeping us on our toes. Time after time she has reinvented her image, her perspective, and most importantly, her music. The lead single from her magnum opus, Ray Of Light, was quite possibly the most unexpected shake up in her career to date, but it paid off in a big way. “Frozen” is a searing electro-ballad that bridged the gap between a rather laborious string of ’90s ballads and her dance floor fillers to come. In its own right, the track was shocking, not for sexual provocation, but for its sincerity, its poignancy, and its simultaneous ability to push boundaries and change the way we think about pop music at a time when what it seemed she needed to do was quite different. “Frozen” is the song that cemented her position, not as a pop star, but as an artist.

01. Like A Prayer

01. Like A Prayer

There are very few championed pop songs as audacious and arousing as “Like A Prayer.” The track has a countless number of aspects that deserve to be highlighted, like its unique structure that effortlessly ebbs and flows in and out of an immaculate chorus, and the addition of the gospel choir that begins by adding a level of beauty and ends up erupting into an exhilarating climax. However, when you boil it down to its barest elements, you’re left with a textbook Madonna classic, and that’s what actually makes it so special. “Like A Prayer” packs in a commanding, funky bass line, lyrics intricately woven with double entendres, and a confident authority seared into Madonna’s delivery, and all of the elements come together in a way that it feels like it’s a meteor sent down to anialate everything we ever knew about pop music. This is a juggernaut that, to this day, no female pop star (or male for that matter) has ever come close to touching, and that’s part of what makes Madonna the Queen of Pop.

 

THE PLAYLIST:

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