The Huffington Post Ranks Madonna Singles

[Angelus 11,476]

Twenty-five years ago, on April 22, 1989, Madonna’s “Like a Prayer” hit No. 1. It has been a pop staple ever since, as have many of the singer’s biggest hits. But something about “Like a Prayer” captured the zeitgeist. Many still call it Madonna’s greatest song — a high honor considering she’s released 68 singles since her debut in 1982. In celebration of what is clearly her defining anthem, we’re ranking all of those songs.

Rubric:
• Billboard Hot 100 success (Many songs made splashes on the Hot Dance Club Play chart and abroad, including some that failed to chart on the Hot 100. For the sake of these rankings, only the Hot 100 performance was considered.)
• Single’s longevity, or: Do people still know it? Is it still played on the radio and in other public arenas?
• How the song contributed to Madonna’s image and critical reception
• Author’s personal taste

What’s missing?
• Promotional singles don’t count (e.g. “Nobody Knows Me,” “Hey You”).
• Featured-artist credits don’t count (e.g. “Me Against the Music” with Britney Spears).
• Any songs that were not released as singles in the United States. Two exceptions: “Into the Groove” and “Fever,” neither of which was technically released as a single. Both were hits in their own right regardless, becoming some of Madonna’s most famous songs.

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UPDATE — March 10, 2015: We’ve begun to adjust our rankings to include the singles from Madonna’s 13th studio album, “Rebel Heart.” First up is “Living for Love,” released in December 2014 following a series of Internet leaks. We’ll add more (and potentially reposition “Living for Love” as its impact continues to unfold) after additional “Rebel Heart” cuts drop.

 

 

• 1 “Like a Prayer” (1989)

  

   

Billboard peak: No. 1

Wherever you are, the opening pings of the organ in “Like a Prayer” are like a call to action. If you’re in public when it begins on your iPod, shove your hands in your pockets immediately to keep from undulating like a member of the song’s gospel choir. If you’re in a karaoke bar, someone better grab that microphone pronto, before another cross erupts into flames as penance for your pop-music sins.

That’s because “Like a Prayer” is among the best pop songs of all time. The hum of the choir at the start crescendos in a way that still demands everyone leap from their seats. It’s just ‘80s enough to have catapulted to ubiquity within weeks of its release, but it’s timeless enough to remain a staple of contemporary-flashback radio.

It helps, too, that the song sparked a flame of controversy. Its video, directed by frequent early-Madonna collaborator Mary Lambert, depicts white supremacy, an interracial romance and Madonna crooning in front of Ku Klux Klan-style burning crosses. It seems tame compared to Madge’s later videos, but the religious controversy resulted in protests. The American Family Association condemned it, and Pepsi, which used “Like a Prayer” in a $5 million advertising deal with Madonna, dropped the singer’s campaign.

Madonna shrugged off the contention, and rightfully so. Critics praised the song, which spent three weeks at No. 1 and has since been listed on Rolling Stone’s and Blender’s lists of the greatest songs of all time. Today, pop stars are lucky to land a song that leads to even half the longevity that “Like a Prayer” has seen. It’s what, more or less, spawned critics’ declaration that Madonna was the high priestess of reinvention. It’s amazing that a number about so many heavy things — religious guilt compounded by one’s devotion to God, mixed with the ideal of doing the right thing and, of course, the thrust of sexual pleasure — doesn’t (and really never did) carry the burden of being an Important Song. Instead, we love it for its dance mandate, its gospel strain and the passion that Madonna’s vocals embody. “Like a Prayer” is indeed a pop-music prayer, answered for the ages.

 

• 2 “Vogue” (1990)

  

   

Billboard peak: No. 1

Second perhaps only to “Like a Virgin” in defining Madonna’s career, “Vogue” has etched a place in the dance-floor lexicon, where it remains more than two decades later. It was the ultimate song of the times. Inspired by ball culture, 1970s disco and downtown New York’s 1980s music scene, “Vogue” became an escapism anthem. The lyrics are apt for the post-Reagan age: “When all else fails and you long to be / Something better than you are today / I know a place where you can get away / It’s called a dance floor, and here’s what it’s for.” The jolted hand choreography is still fashionable today, as evidenced by its use during the sleek opener of Madonna’s 2012 Super Bowl halftime show — 24 years after her MTV Video Music Awards performance transformed the song into an astounding ode to Marie Antoinette-era France, 18 years after Robin Williams gave it a sendup in a memorable scene from “The Birdcage,” and eight years after it opened the “Devil Wears Prada” soundtrack.

Today, “Vogue” remains a staple of Madonna’s setlists, and the video, directed by a young David Fincher, is a black-and-white portrait of 1920s Hollywood with a postmodern slant. The song is often credited with having helped to bring house music to the fore, so thank or curse Madonna for that as you will. Either way, “Vogue” is a song that’s worth striking a pose for

 

• 3 “Express Yourself” (1989)

  

   

Billboard peak: No. 2

Another fixture of radio airwaves, supermarket speakers and dance floors, “Express Yourself” has never not been relevant. Still, a little song called “Born This Way” came along in 2011, and again the words “Express Yourself” were on everyone lips. What resulted was a fierce debate about whether Lady Gaga had appropriated the chord structure of Madonna’s 1989 hit. Once again, another female pop artist seemed to, at least, pay homage to Madge or, at most, have totally ripped her off. “As far as Western music theory is concerned, that song was written by Madonna,” Owen Pallett said of “Born This Way” in a Slate essay.

Whichever position you take in the great Madonna-Lady Gaga debate of the 2010s, there’s no doubt that “Express Yourself” is an iconic song. It serves as many things: a female-empowerment anthem, the antithesis of the literalism interpreted in 1984’s “Material Girl” (pure satire, but irony doesn’t always mesh with pop music), and the singer’s most concerted effort to drift from the bubblegum stylings of her previous work. The music video — Madonna’s first collaboration with David Fincher and, with a $5 million budget, one of the most expensive ever made — was in 2011 ranked among TIME’s 30 greatest of all time.

 

• 4 “Justify My Love” (1990)

  

   

Billboard peak: No. 1

Ah, “Justify My Love.” Where does one begin when describing a song that is iconic for entirely different reasons than every other high-ranking track on this list? It’s unlikely you’ll hear “Justify My Love” on the radio today, and the same goes for the dance floor, the supermarket, on television and, in all likelihood, on your iPod. Yet somehow it remains one of the singer’s most epochal, and for that we must celebrate it.

The song instantly conjures images of its grainy black-and-white video, which featured Madonna slinking through the halls of a hotel while engaging in cloistered acts of sexual passion, at times wearing nothing but skimpy undergarments and donning a dominatrix mien. With androgyny and fetishism as primary themes, the video earned the rare distinction of being banned from MTV’s airwaves. To top it off, “Justify My Love,” co-written by Lenny Kravitz and Ingrid Chavez, sounded like no song Madonna had ever made. Most of its lyrics are spoken with breathy cadence, enhancing the trip-hop ode’s carnal energy. “Justify My Love” has striking psychedelic influences, and it ushered in the “Erotica” period that would define the singer’s image throughout the first half of the ‘90s. All that for a song that was banned from seeing the light of day.

 

• 5 “Like a Virgin” (1984)

  

   

Billboard peak: No. 1

“Like a Virgin” is synonymous with Madonna. “Like a Virgin” is synonymous with weddings. “Like a Virgin” is synonymous with teeny-bopper lookalikes dressed in dangling beads and evening gloves. And, most importantly, “Like a Virgin” is synonymous with the MTV Video Music Awards, where, during its inaugural 1984 ceremony, Madonna famously rolled around on the stage and instantly became a global superstar. (Another twist of charisma, as no one even knew “Like a Virgin” when she performed it that night. It wouldn’t be released as a single for another two months.) Nineteen years later, “Like a Virgin” appeared on the VMA stage again, this time sung by 2003’s reigning pop princesses, Christina Aguilera and Britney Spears, who donned wedding gowns and locked lips with their musical matron. The classic still felt as fresh as ever.

Much of pop music is owed to both the song and the 1984 VMA performance it inspired. Nile Rodgers, who produced the “Like a Virgin” album, famously told Madonna at first that the track’s hook and lyrics weren’t catchy — a critique for which he soon apologized. “Like a Virgin” introduced the first major controversy of Madonna’s career, and once she’d had a taste, she never let that reputation drift far from her namesake. No one lambastes its sexual undertones anymore, but Madonna has maintained the song’s association with controversy. On her acclaimed 1990 Blonde Ambition Tour, she simulated masturbation on a red silk bed during a Middle Eastern-themed arrangement. During 2008’s Sticky & Sweet Tour, she dedicated it to the pope. And on 2012’s MDNA Tour, she performed it as a piano ballad. So while you were making sure the DJ at your wedding included it on the playlist (because what are a few naughty lyrics when a song is this catchy?), Madonna was ensuring it remained true to her original intentions: to grab your attention and stir up some agitation, the way only a timeless pop standard can.

 

• 6 “Ray of Light” (1998)

  

   

Billboard peak: No. 5

By the time the “Ray of Light” album arrived in February 1998, the world was well-adjusted to Madonna’s self-reinventions. This one offered the steepest departure from her previous work. By the time she became a mother in late 1996 and then won the Golden Globe for her celebrated role as Eva Perón in “Evita,” Madonna converted to Kabbalah and found spiritual enlightenment. The result was a stunning tour de force of songwriting and William Orbit-produced electronic rock. The album’s titular second single didn’t peak as high as some of her previous Billboard hits, but no matter: It defined a more adult Madonna while managing to be just as memorable as what had come before.

“Ray of Light” is a rock anthem. It’s often noted for its dance vibe, but what resounds is its use of electric guitar. It co-existed with the apex of the 1990s’ female singer-songwriter evolution but joins the proliferation of electronic music that emerged around the same period — all while maintaining the psychedelic undertones offered on the “Erotica” and “Bedtime Stories” albums. “Ray of Light” became the comeback story Madonna didn’t even know she needed: a post-40 pop-rock goddess returning to her throne, emboldened by a spiritual renaissance. The album and its title track led to a huge night at the Grammys for Madonna. She lost Album of the Year in a heated battle with Lauryn Hill but nabbed Best Pop Vocal Album and Best Dance Recording. “Ray of Light” is wonderful because it’s a brilliant song, but it’s important because, 15 years after her first single, it cemented Madonna’s longevity and ushered in another several years of pop sovereignty.

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  7 “Human Nature” (1995)

  

   

Billboard peak: No. 46

Listening to “Human Nature” might leave you scouring the liner notes for a Dr. Dre credit. You won’t find it, but the song’s hip-hop influences are undeniable. It wasn’t a huge Billboard hit, yet the bondage-inspired video — in which Madonna trots around in cornrows and a skintight leather suit while carrying a chihuahua in one hand and a whip in the other — became iconic in its own right, and she’s since performed the track on numerous world tours. Released months before “Evita” would usher in a more harnessed iteration of her career, “Human Nature” marked the cessation of Madonna’s hypersexual phase. The aggressive lyrics (“I’m not your bitch, don’t hang your shit on me”) acted as a response to the backlash “Erotica” and the “Sex” book received, because Madonna is nothing if not self-aware. “Human Nature” is an R&B blitz that remains one of Madonna’s most original songs, particularly as her early-‘90s era has gained esteem in the years since it lit the country’s moral compass on fire.

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  8 “Holiday” (1983)

  

   

Billboard peak: No. 16

“Holiday” is further evidence of Madonna’s longevity. It was her first hit, and it prevails as one of her defining fixtures, even though it never cracked the Top 10. It’s certainly her most infectious song. Who doesn’t want to imagine “Holiday” scoring their arrival at a Hawaiian resort? Much in the way that “Like a Virgin” is defined by its wedding association, the upbeat “Holiday” lyrics make it the world’s vacation paean.

The song premiered to acclaim, but no one foresaw Madonna’s impending rise to supremacy. “Holiday” came and went like any old one-off pop hit, and yet it endures, having become a staple of the singer’s tours and an epitomization of ‘80s bubblegum cheer. Plus, Madonna is credited for the song’s cowbell.

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  9 “Material Girl” (1984)

  

   

Billboard peak: No. 2

“Material Girl” holds an interesting place in Madonna’s oeuvre. Released after “Like a Virgin,” it was a substantial hit that today is most readily associated with the nickname it lent to the singer. Yet “Material Girl” is the song Madonna has worked hardest to shed from her image.

It was meant as satire, a parody of society’s one-note approach to glamour and wealth. The music video’s “Gentlemen Prefer Blondes” portrait of Marilyn Monroe is still iconic, even though her three most recent tours haven’t included the song on their setlists. But first impressions are everything, and there’s no diminishing the power any follow-up to “Like a Virgin” could have wielded. If anything, the “Ray of Light,” “Music” and “American Life” albums were rebuttals to everything fans failed to appreciate in “Material Girl.” The song’s intent may register more clearly today, but no one’s tending to that while they slap the Material Girl moniker on Madonna’s shoulders at every turn. (If you don’t want to dote to that addendum, that’s okay, too — the song is still pure fun.)

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  10 “Into the Groove” (1985)

  

   

Billboard peak: N/A

“Into the Groove” was a crossover hit from the “Desperately Seeking Susan” soundtrack, yet it was never officially released as a single for fear it would go head to head with “Angel,” her third outing from the “Like a Virgin” album. It was a silly decision on Warner Bros.’ part, because no one (including this ranking) cites “Angel” as one of Madonna’s more memorable singles. But “Into the Groove” is. It follows the same tempo as “Holiday” and in turn serves as Madonna’s finest pre-“Vogue” dance-floor anthem. “Into the Groove” is the ultimate mid-‘80s call to action.

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  11 “Music” (2000)

  

   

Billboard peak: No. 1

Madonna’s most recent No. 1 single, “Music” marked another resurgence for the singer. Here came full-on Electronic Madonna, who imbued her club-friendly grooves with mature sensibilities. The song’s opening words — “Hey, Mr. DJ, put a record on / I wanna dance with my baby” — also helped to introduce the DJ renaissance in which artists name-checked record spinners in their music. Jennifer Lopez, Mariah Carey, Black Eyed Peas, Jet, Lil Wayne and Britney Spears are among the artists who followed suit.

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  12 “Lucky Star” (1983)

  

   

Billboard peak: No. 4

Madonna’s most ‘80s-sounding hit, “Lucky Star” spawned the bulk of the copycat costumes still seen at Halloween parties far and wide. “Lucky Star” made Madonna a fashion icon. It was her first Top 5 Billboard hit, propelled by the seminal look first seen in the music video. Teen girls everywhere emulated her black mesh top and bangles, the rosary worn as jewelry and the unruly hair tied up in a ribbon.

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  13 “Frozen” (1998)

  

   

Billboard peak: No. 2

“Frozen” preceded “Ray of Light,” and landed in a higher position on the Billboard chart than that track, but it hasn’t secured the same longevity. Still, critics extolled the song, hailing the haunting ballad as a “breathtaking“ “masterpiece“ of ‘90s pop-rock. The drum beat is dazzling.

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  14 “Papa Don’t Preach” (1986)

  

   

Billboard peak: No. 1

The sweeping string arrangement that mounts “Papa Don’t Preach” is still among pop music’s most engaging openings. It’s a song that made everyone mad: Anti-abortion groups saw it as pro-life; pro-choice organizations thought it undermined birth control by promoting teen pregnancy. As usual, none of that mattered in the end, as the song’s popularity has only escalated over the years. In 2002, Kelly Osbourne put it back on the Billboard chart with her cover.

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  15 “Hung Up” (2005)

  

   

Billboard peak: No. 7

“Hung Up” sounds like a sendup to the club-friendly dance music Madonna made in the ‘80s, its chugging beat serving as her catchiest since “Vogue.” Come for the tune’s ticking-clock groove, stay for the video’s acrobatic dance. You try doing either at 47.

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  16 “Hollywood” (2003)

  

   

Billboard peak: Didn’t chart

Pay no attention to the fact that this searing “American Life” track failed to chart. “Hollywood” is one of Madonna’s most layered lyrical achievements, and it will never be far from her canon thanks to that infamous MTV Video Music Awards performance where she smooched Britney Spears and Christina Aguilera while singing this song.

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  17 “Borderline” (1984)

  

   

Billboard peak: No. 10

“Borderline” is credited with helping to cement Madonna’s signature ‘80s sound. It’s all about those wailing vocals and the barrier-breaking video, which depicted a rare interracial romance.

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  18 “Secret” (1994)

  

   

Billboard peak: No. 3

The seductive “Secret” hails from the same hip-hop influences that made “Justify My Love” and “Human Nature” instant classics. In the weeks leading up to its release, Madonna made what was then considered an unprecedented move: She unveiled a snippet of the song on the Internet along with the cover art for the then-unreleased “Bedtime Stories.”

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  19 “Take a Bow” (1994)

  

   

Billboard peak: No. 1

Co-written by Babyface, “Take a Bow” is Madonna’s most poetic ballad. Much in the way that such hits as “Borderline” and “Into the Grove” act as the fuselage of ‘80s pop, “Take a Bow” is a lost-love elegy that squares nicely with the burgeoning female singer-songwriter movement of the ‘90s. Don’t mistake its sleepy quality for stuffiness — this song is Madonna at her loveliest.

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  20 “Living for Love” (2014)

  

   

Billboard peak: TBD

Widely hailed as Madonna’s best single since “Hung Up,” this post-breakup empowerment anthem channels the matador theme of “Take a Bow” and the pumped-up bravado of “Express Yourself.” Thanks to a triumphant Grammy performance less than two months after “Rebel Heart” leaks forced Madonna to release some of the album early, “Living for Love” ushered in the singer’s biggest renaissance in a decade. Brit Awards tumble be damned — the clever lyrics and piano-backed house rhythms make it a Madonna essential.

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  21 “Don’t Tell Me” (2000)

  

   

Billboard peak: No. 4

One of the standouts from the “Music” album, the country-inspired “Don’t Tell Me” thrived because it was such an unlikely follow-up to the electronic-infused title single. It saw a recent revival when Madonna joined Miley Cyrus to perform the song on “MTV Unplugged.”

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  22 “Beautiful Stranger” (1999)

  

   

Billboard peak: No. 19

If the psychedelia embedded on “Erotica” was a piece of that album’s hodgepodge pie, “Beautiful Strange” is a pure sendup to the genre. The silly “Austin Powers: The Spy Who Shagged Me” anthem isn’t likely to appear on any future tour setlists, but it’s her most unabashedly fun release to date.

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  23 “Erotica” (1992)

  

   

Billboard peak: No. 3

Released at the apex of Madonna’s sex appeal, “Erotica” and its accompanying title album are remarkable as a period of innovation for the singer. The song saw mixed reviews, but it’s still amazing to realize that something with coital moans underscoring the lyrics charted as high as it did in 1992. The stylized video — shot with Super 8 film and featuring Naomi Campbell, Isabella Rossellini and Big Daddy Kane — used scenes from the making of Madonna’s “Sex” book. MTV aired it only a few times due to the graphic content.

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  24 “Everybody” (1982)

  

   

Billboard peak: Didn’t chart

“Everybody” carries a clear directive: “C’mon, dance and sing.” Madonna’s debut single, it ushered in what she would inspire us to do for the next 32 years (and counting).

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  25 “Open Your Heart” (1986)

  

   

Billboard peak: No. 1

“Open Your Heart” is among the songs that introduced the famous cone bra worn on 1990’s Blonde Ambition Tour — the same one that in 2012 sold for $52,000.

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  26 “Don’t Cry for Me Argentina” (1996)

  

   

Billboard peak: No. 8

“Don’t Cry for Me Argentina” is one of the most important songs to Madonna’s career. The image of her serenading Buenos Aires with Andrew Lloyd Webber and Tim Rice’s “Evita” aria serves as a stand-in for the transition from Sexy Madonna to Adult Madonna. Plus, she won a Golden Globe for her performance in the movie.

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  27 “Nothing Really Matters” (1999)

  

   

Billboard peak: No. 93

“Nothing Really Matters,” or: The song where Madonna went all “Memoirs of a Geisha” on us. It’s one of her weirdest videos and one of her most underrated gems. The downtempo track rounded out the cadre of brilliant singles released from “Ray of Light.”

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  28 “4 Minutes” (2008)

  

   

Billboard peak: No. 3

It sounds like a marching band is barreling through “4 Minutes,” as if Madonna, alongside collaborators Justin Timberlake and Timbaland, is embarking on one final hip hop romp before the apocalypse. Their effort to “save the world” results in an infectious dance anthem that should have been a No. 1 hit.

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  29 “True Blue” (1986)

  

   

Billboard peak: No. 3

“True Blue” is just as retro-catchy today as it was when it genuflected to ‘50s-style girl groups in 1986. Taken as anything other than homage, it’s a silly, meandering tune. But heard as a could-be outtake from the “Grease” soundtrack, “True Blue” is a song that’s still worthy of singing into your hairbrush in the bathroom mirror.

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  30 “Fever” (1993)

  

   

Billboard peak: Didn’t chart*

Madonna’s satiny “Fever” remake injects a techno groove into the song, making an already seductive ditty even more sultry. Plus, there’s that famous “Saturday Night Live” performance.

*“Fever” was never officially released as a single, thereby making it ineligible for the Hot 100. It was a dance smash, however, reaching No. 1 on the Hot Dance Club Play chart, and its video received a sizeable TV rotation, which is why this ranking makes an exception for the song.

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  31 “Live to Tell” (1986)

  

   

Billboard peak: No. 1

“Live to Tell” introduced Madonna’s first polished image, her inaugural post-“Like a Virgin” makeover. It was praised for its lyrics and moody atmosphere.

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  32 “This Used to be My Playground” (1992)

  

   

Billboard peak: No. 1

“This Used to be My Playground” was written for “A League of Their Own,” but it became a smash in its own right. What’s surprising is that the heartfelt ballad’s release was sandwiched between “Justify My Love” and “Erotica,” which corroborates the many checkered crowns that Madonna can wear.

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  33 “Dress You Up” (1985)

  

   

Billboard peak: No. 5

Years before Madonna burned crosses and posed nude in a coffee table book, “Dress You Up” faced the wrath of Tipper Gore’s Parents Music Resource Center, which listed it among the 15 songs with the most objectionable lyrics. In truth, this one’s quite mild and quite fun, as evidenced in the popular 1999 Gap commercial that sampled it.

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  34 “Bad Girl” (1993)

  

   

Billboard peak: No. 36

The classiest cut on “Erotica” is “Bad Girl,” a sizzling ballad about the desire for romance. The video stars Christopher Walken as Madonna’s guardian angel.

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  35 “Deeper and Deeper” (1992)

  

   

Billboard peak: No. 7

“Deeper and Deeper” is about a boy coming to terms with his homosexuality. It’s Madonna’s finest disco flourish.

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  36 “Bedtime Story” (1995)

  

   

Billboard peak: No. 42

Björk co-wrote this ambient trance outing, which is Madonna’s most hypnotic song. Mark Romanek directed the $5 million video before helming such seminal ‘90s clips as Michael Jackson and Janet Jackson’s “Scream” and Fiona Apple’s “Criminal.”

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  37 “Sorry” (2006)

  

   

Billboard peak: No. 58

Many critics called the “throbbing,” “catchy“ and “triumphant“ “Sorry” the best cut from “Confessions on a Dance Floor.”

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  38 “The Power of Good-Bye” (1998)

  

   

Billboard peak: No. 11

You hardly notice the clinking noises underneath this song’s orchestration, and that’s supreme praise. The “Frozen” cousin’s production is stunning amid Madonna’s serene vocals, resulting in a sleek meditation on dismissed love.

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  39 “Love Profusion” (2003)

  

   

Billboard peak: Didn’t chart

“Love Profusion” is a lovely folk song for the electronic era.

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  40 “Get Together” (2005)

  

   

Billboard peak: Didn’t chart

Madonna didn’t lose her enlightenment with the final chords of “Ray of Light.” If it seems like the singer traded in substance for synthesizers after “American Life,” this catchy tune begs to differ. “Do you believe that we can change the future?” she croons.

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  41 “Burning Up” (1983)

  

   

Billboard peak: Didn’t chart

Somewhere there’s a jazzercise class still breaking a sweat to this song, which sounds like an outtake from the punk persona Madonna never fully embraced.

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  42 “La Isla Bonita” (1987)

  

   

Billboard peak: No. 4

Madonna used “La Isla Bonita” as an ode to Latin music’s infusion in pop standards. It’s long been one of the singer’s more well-received songs. But you have to be in the right mood for this one — its middling tempo can feel like a slog.

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  43 “Rain” (1993)

  

   

Billboard peak: No. 14

The penultimate single from “Erotica,” “Rain” was a departure from the carnal outings that came before it. It’s not terribly distinctive from the other ballads Madonna released in the early ‘90s, but then there’s that great video and the sultry chorus with the uplifting lilt “Here comes the sun.”

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  44 “American Life” (2003)

  

   

Billboard peak: No. 37

This song landed Madonna on GQ’s list of the 25 worst rappers of all time and its pro-materialism reverses much of what she tried to jettison in her post-“Material Girl” efforts, but that shouldn’t convince you “American Life” isn’t an underrated single. That rap solo (“I drive my Mini Cooper / And I’m feeling super-duper / Yo, they tell I’m a trooper / And you know I’m satisfied”) rightfully raises eyebrows — okay, fine, it’s terrible — but the video’s controversial political violence once again put the singer in the hot seat. Good thing the song’s so memorable.

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  45 “I’ll Remember” (1994)

  

   

Billboard peak: No. 2

The delicate chug of “I’ll Remember” is still most apt as the opening credits of a ‘90s dramedy. Fitting, as it’s the theme from the 1994 movie “With Honors.” On the heels of ferocious criticism from the aftermath of “Sex” and “Erotica,” the song helped to soften Madonna’s image.

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  46 “Causing a Commotion” (1987)

  

   

Billboard peak: No. 2

“Causing a Commotion” sounds cheerful, but Madonna told Rolling Stone in 1987 that it was inspired by her abusive relationship with Sean Penn.

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  47 “Crazy for You” (1985)

  

   

Billboard peak: No. 1

The song that bumped “We Are the World” from its Billboard perch, “Crazy for You” at the time featured Madonna’s strongest vocals and may still be her greatest love ballad. It’s dull by today’s standards, however, and “Crazy for You” has fallen off despite having been a Grammy-nominated hit.

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  48 “What It Feels Like for a Girl” (2000)

  

   

Billboard peak: No. 23

A perplexing choice for a single, “What It Feels Like for a Girl” is nonetheless a meaningful lyrical accomplishment. The violent video, directed by Guy Ritchie, was banned from MTV and VH1.

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  49 “Jump” (2006)

  

   

Billboard peak: Didn’t chart

Madonna’s glassy low register makes “Jump” the grittier sequel to “Vogue.” The Pet Shop Boys should be pleased, as the song is an homage to “West End Girls.”

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  50 “Girl Gone Wild” (2012)

  

   

Billboard peak: Didn’t chart

“Girl Gone Wild” is Madonna trying a little too hard to emulate a song that Britney Spears could have recorded. The lyrics are clichéd and the pulsating beat overwrought, but you try listening to the song once without singing it back to yourself all day. Plus, it provides Madonna’s best video since “Frozen.”

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  51 “Cherish” (1989)

  

   

Billboard peak: No. 2

Even though it’s the most cloying of the songs often listed as Madonna’s biggest hits, “Cherish” holds a special place in her repertoire. It was released on the heels of “Like a Prayer” and “Express Yourself,” again reminding the world that her statements on race and feminism could coexist with bubblegum-dance sensibilities.

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  52 “Who’s That Girl” (1987)

  

   

Billboard peak: No. 1

This Spanish-influenced song from the film of the same title earned Grammy and Golden Globe nominations but may be Madonna’s least-remembered No. 1 hit.

•  

  53 “Hanky Panky” (1990)

  

   

Billboard peak: No. 10

The innuendo-laden “Hanky Panky” is pure fun, ‘50s swing style. The lyrics are sillier than they ought to be, but the fabulous beat refuses to let your dancing shoes collect dust.

•  

  54 “Die Another Day” (2002)

  

   

Billboard peak: No. 8

As a song, “Die Another Day” packs melodrama where it should find a hook. But as a Bond anthem, it’s the perfect way to introduce the action series to the 21st century.

•  

  55 “Give It 2 Me” (2008)

  

   

Billboard peak: No. 57

The Neptunes produced “Give It 2 Me,” which features Pharrell Williams on backing vocals. It’s a throbbing empowerment anthem that contains one of Madonna’s more clever references to her own career: “Give me a record and I’ll break it.”

•  

  56 “Revolver” (2009)

  

   

Billboard peak: Didn’t chart

Madonna should have skipped “Revolver” as a single choice in favor of the similar but much better “MDNA” installment “I’m Addicted.” Still, the angry track features Lil Wayne and could have been a big hit for Rihanna.

•  

  57 “Give Me All Your Luvin’” (2012)

  

   

Billboard peak: No. 10

“Give Me All Your Luvin’” contains Madonna’s most vacuous lyrics, which includes M.I.A. and Nicki Minaj chanting “L.U.V. Madonna!” It’s proof “MDNA” needed the singer to graduate from vapid sentiments like “Don’t play the stupid game / ‘Cause I’m a different kind of girl.” Still, its new-wave influences help to make it a rousing ditty, and Minaj’s brief rap verse is great.

•  

  58 “Rescue Me” (1991)

  

   

Billboard peak: No. 9

Madonna speaks throughout much of “Rescue Me,” but it’s hardly as effective a technique here as it is on “Justify My Love,” which preceded it as a single. The chorus, however, in which Madonna digs deep into her low register to belt out the words “rescue me,” is a marvel.

•  

  59 “Nothing Fails” (2003)

  

   

Billboard peak: Didn’t chart

“Nothing Fails” was too mature to be a hit, so Maverick released a remixed version that doesn’t quite work. With its acoustic guitar and gospel choir, the original is folksy and reflective of the underrated quality of “American Life.”

•  

  60 “Angel” (1985)

  

   

Billboard peak: No. 5

Following the succession of “Holiday,” “Lucky Star,” “Borderline,” “Like a Virgin,” “Material Girl” and “Crazy for You,” “Angel” comes off as a subpar single.

•  

  61 “You Must Love Me” (1996)

  

   

Billboard peak: No. 18

Tim Rice and Andrew Lloyd Webber wrote “You Must Love Me” for “Evita,” and it went on to win the Oscar for Best Original Song. The vocal training Madonna endured for the movie pays off in this soprano serenade, but the song doesn’t do much outside of the film.

•  

  62 “Celebration” (2009)

  

   

Billboard peak: No. 71

“Celebration” is another dance invitation, but it lacks the originality of “Vogue” or the appeal of “Jump.”

•  

  63 “Keep It Together” (1990)

  

   

Billboard peak: No. 8

Sly and the Family Stone influenced “Keep It Together,” a devotion to the importance of family. The beat is too busy to be very memorable, but the song marked the finale to Madonna’s more innocent ‘80s, arriving right before “Vogue” and “Justify My Love” inaugurated her most provocative chapter.

•  

  64 “Miles Away” (2008)

  

   

Billboard peak: Didn’t chart

“Miles Away” is reminiscent of Justin Timberlake’s “What Goes Around... Comes Around,” likely because JT — along with Timbaland and Danja — co-wrote it. It’s a good track that would have been better had Madonna skipped the computerized effects and instead drawn from its folk foundation.

•  

  65 “Turn Up the Radio” (2012)

  

   

Billboard peak: Didn’t chart

Madonna looks impeccable in the video for “Turn Up the Radio,” which offers refreshing production values that employ her electronic infatuation without becoming too wired. Sadly, the lyrics are just plain awful.

•  

  66 “American Pie” (2000)

  

   

Billboard peak: No. 29

Madonna’s cover of the 1976 Don McLean classic “American Pie” was largely panned, but McLean himself praised it, calling the remake “sensual and mystical.” It’s not a bad song, per se, it’s just a fluffy dance-pop approach to one of rock’s greatest anthems.

•  

  67 “Oh Father” (1989)

  

   

Billboard peak: No. 20

“Oh Father” has a lush string arrangement, but it was kind of boring then and it’s still kind of boring now.

•  

  68 “Love Don’t Live Here Anymore” (1996)

  

   

Billboard peak: No. 78

Madonna included her remake of Rose Royce’s “Love Don’t Live Here Anymore” on the “Like a Virgin” album, but she released a remix in conjunction with the 1995 ballads album “Something to Remember.” Her impassioned croons don’t work as a sultry R&B jitter.

•  

  69 “You’ll See” (1995)

  

   

Billboard peak: No. 6

“You’ll See” was the first single released after “Bedtime Stories,” so it could be credited as a curtsy to Madonna’s impending “Evita”/“Ray of Light” comeback. Unfortunately, it also sounds like a dull displacement from a compilation of yearning ‘80s ballads.

 

 

 

 

[Saiga 16,485]

Bedtime Stories winning

[Angelus 11,476]

2 minutes ago, Saiga said:

Bedtime Stories winning

Not on charts

[Angelus 11,476]

Not them hating some of her most acclaimed songs like La Isla Bonita, Oh Father and Live Yo Tell

But they also paid attention to hot 100 chart so some positions are probably based on that.

[havok 1,971]

I can't at LAP always being #1. Like yes, it's a masterpiece but come on. 

Human Nature should have been top 5. It's a known fact of course, but this just reminded me of how fucking flawless her discog is. 

[SeekingThrill 10,041]

LAV, Hollywood...

 

Some of her best stuff have bad positions.

 

Fever slaying.

[Vertigo-go 18,832]

Into the Shit is her worst song ever

[Saiga 16,485]

1 hour ago, Vertigo-go said:

Into the Shit is her worst song ever

[Vertigo-go 18,832]

7 minutes ago, Saiga said:

[Mdolla82 16]

OH Father and its video are masterpieces.