With all due respect (and possible future apologies) to Beyoncé, whose path recently overlapped with hers on the “Vogue”-sampling “Break My Soul (The Queens Remix),” Madonna is set this week to remind the world why she is the best-selling female recording artist of all time and one of the most influential stars in pop history. Even without torch-passing MTV “triple kisses” with Britney Spears and Christina Aguilera, or the conspicuous similarities between “Express Yourself” and Lady Gaga’s “Born This Way,” the single-monikered singer, songwriter, and actress has made a singular and irrefutable impact on music, videos, stage performance, filmmaking, and the very notion of celebrity. Madonna has the most number one singles by a woman in Australia, Canada, Italy, Spain, and the U.K., holds the number two spot on U.S. Billboard’s Hot 100 chart, and has the highest grosses of any worldwide-touring female artist.
The compilation Finally Enough Love, due on August 19, commemorates another of her achievements: being the only recording artist with 50 Number One songs on any Billboard chart. To prevent our staff from descending into chaotic factions as they debated which of her albums—or eras—was her best, The A.V. Club decided to rank just Madonna’s number one songs on the Billboard Pop Chart. For some, the remarkable takeaway of this ranking will be the number of stone-cold classics that are excluded because they didn’t reach the top spot. Still, the 12 tracks featured here chart a path through Madonna’s chameleonic career while underscoring her growth and versatility as arguably the defining pop artist of the past four decades.
12. “This Used To Be My Playground” (1992)—A League Of Their Own Soundtrack
A trailblazer rather than a copycat, Madonna has always been averse to nostalgia—in her songs and her career as a whole. Even when revisiting her greatest hits on tour, she reinvents them in some fashion or another. This maudlin ballad about glory days gone by just feels out of sync with the rest of her catalog. She wrote the song at the request of Penny Marshall for the movie A League Of Their Own, which she also starred in.
Madonna has gone on record since then about “Playground,” calling the song “assignment writing.” Clearly, she did something right, since it reached No. 1. But as the only Madonna song that feels a little too “mom approved,” it seems less cool than her other songs—especially those on this list. Perhaps that’s why Madonna herself doesn’t seem to have much love for it either: she’s never performed it live. [Eric Diaz]
11. “Who’s That Girl” (1987)—Who’s That Girl Soundtrack
This is a Madonna song that casual fans seem shocked to discover was a number one hit—seriously, “Who’s That Girl” went to the top, but not “Express Yourself” or “Material Girl,” which both stalled at number two These days only hardcore fans vividly remember this lightweight title track to her 1987 comedy film of the same name, which itself was a flop. That said, it feels a bit like a catchy, upbeat, and less ponderous sequel to the more famous “La Isla Bonita,” so much so that Madonna even gives us more spoken-word Spanish.
She worked on this song with True Blue producers and frequent collaborators Stephen Bray and Patrick Leonard, recording it all in one day. It’s not as strong as that album’s iconic hits, but it’s a passable effort—even if a few other songs from that phase of her career are more deserving of a top spot. [Eric Diaz]
10. “Papa Don’t Preach” (1986)—True Blue
Madonna’s fourth number one hit was the second single from her 1986 album True Blue, the record that proved she was an artist with staying power. It’s also the kind of track that’s almost extinct these days: the “story song,” where the singer adopts the role of a fictional character. (Cher made a whole career of this in the early ’70s). From the opening string arrangement to every heartfelt plea for her “Daddy, Daddy” not to reject her for getting pregnant, this cut is pure gold, even when it teeters into sentimentality.
Written by Brian Elliot, this is the rare song that drew criticism for Madonna from the left and right alike. Conservatives thought she was promoting teenage sex and promiscuity, while liberals thought the song meant Madonna was anti-abortion. Neither is true, but Madonna rode those slings and arrows all the way to the top of the charts. Somehow, she made an up-tempo and danceable pop track about the impossible choice a young woman has to make about her pregnancy. That the charts embraced it then, and that it somehow manages not to offend now, only reiterates why she’s still the queen of pop. [Eric Diaz]
9. “Crazy For You” (1985)—Vision Quest Soundtrack
If you ever slow-danced in high school during the ’80s, this Madonna song must be seared into your soul. By the time “Crazy For You” hit the airwaves in the spring of 1985, Madonna was on a massive roll. She’d had five big hits within 15 months, even though critics were calling her a one-trick pony. When “Crazy For You” hit, it proved she was as capable with ballads (albeit a sexy one) as with upbeat pop earwigs.
Composed for the romantic coming-of-age movie Vision Quest, in which Madonna made a cameo, this song captures lustful teen longing better than virtually any track of its era. Fun fact about this single’s chart success: after the 1985 American Music Awards ceremony, producer Quincy Jones gathered almost every artist attending to record “We Are The World” that same night. Madonna, who was at the awards, was not invited. Which song later knocked “We Are the World” out of its number one position “Crazy For You,” which would double as the sound of Madonna’s delicious revenge. [Eric Diaz]
8. “Justify My Love” (1990)—The Immaculate Collection
When a major musical act releases a greatest hits package, they usually include a couple of forgettable new songs. Madonna defied that tradition by releasing the sexually charged “Justify My Love” in 1990 as part of her The Immaculate Collection compilation. Written by Lenny Kravitz and Prince protégé Ingrid Chavez—the latter eventually won a lawsuit giving her a songwriting credit for the track—the song uses the same hypnotic drumbeat as Public Enemy’s “Security Of The First World,” which Madonna amplifies with smoking hot spoken-word come-ons.
A full-on ode to desire that would telegraph her shift into more sexually explicit material in both her Sex art book and the 1992 album Erotica, “Justify” is thirst in musical form. The controversy over its music video—a black and white romp featuring fetish wear, light BDSM, and a whole lot less nudity than the hand-wringers would have you believe—undoubtedly drove the song’s popularity. But even after being banned from MTV, and eventually being released as a VHS single, the first ever for an American artist, the unabashedly horny song was a huge radio hit during the conservative Bush the First heyday, shooting all the way to number one in record time. Today, it remains one of Madonna’s sexiest bangers, setting the stage not only for her still-underrated Erotica era but her tireless capacity to transform and provoke. [Eric Diaz]
7. “Live To Tell” (1986)—True Blue
By her third studio album True Blue, Madonna was determined to establish herself as a serious artist—so much so that she released this introspective ballad as the lead single. (Yes, ahead of “Papa Don’t Preach,” “Open Your Heart,” “La Isla Bonita,” and the title song.) While the melodramatic accompaniment came from longtime collaborator Patrick Leonard, who originally composed it for a rejected score to the film Fire With Fire, Madonna wrote the song’s lyrics to suit her then-husband Sean Penn’s film At Close Range, probing into themes of deceit, mistrust, and perseverance.
Accompanied by a decidedly more demure look in the cover art and its later music video, Madonna’s strategy paid off—not just with a number one on the Billboard pop chart but on the Adult Contemporary chart as well. Leonard’s music certainly contained the seeds of what the song would become, which is why he doubled down on them in his complete score. It’s also a testament to Madonna’s contributions that you can’t watch the film without thinking of her vocals, scene to scene, every time his melody sneaks underneath what’s on screen. [Eric Diaz]
6. “Like A Virgin” (1984)—Like A Virgin
To this day, “Like A Virgin” probably remains the song most synonymous with Madonna. It’s the track that launched her into the pop culture stratosphere, making her a household name overnight with a sense both for great hooks and for generating controversy. The song probably wouldn’t make a list of her 20 best songs—she’s made much more interesting singles in the decades since. But the track is as iconic as she is, a permanent part of the pop culture firmament.
Although written by the hit-making songwriting duo Tom Kelly and Billy Steinberg (“True Colors,” “Eternal Flame”), no artist wanted the song at first. But Madonna saw its potential, and enlisted producer Nile Rodgers to iron out the kinks, giving birth to an instant hit. Despite her cheerful dispute with Quentin Tarantino after he referenced it—vividly—in the writer-director’s Reservoir Dogs (“it’s about love, not dick,” she said in a note after seeing the film), “Like A Virgin” is notable for being one of the first number one songs by a woman that’s forthright about wanting to get laid. But as a metaphor or a literal expression of desire, Madonna fearlessly made girls around the world sing along on the radio to a song about getting their cherry popped. [Eric Diaz]
5. “Music” (2000)—Music
Madonna was 42—more than a decade past retirement age in pop years—when she released her eighth studio album, Music. Despite a coming wave of teen and twentysomething stars who were eager to claim her throne, she demonstrated why she had been crowned Queen of Pop in the first place with the lead single, that album’s hypnotic, pulsing title track.
As she’d done on her three previous records, Madonna sought out the next great producer on the horizon—this time, French artist Mirwais Ahmadzai—who led her away from the eclectic, contemplative electronica of Ray Of Light and towards a futuristic version of the dance sounds that helped establish her career. (Certainly, there could be no “Music” without “Burning Up” before it.) While paying homage to the four-four dance-floor fillers that inspired an ambitious dancer named Madonna Louise Ciccone to try her hand at pop songwriting, Ahmadzai manages to capture both the artist’s endless youthfulness and her constantly evolving maturity, creating another classic equally suited to a cavernous nightclub or a snug pair of headphones. [Todd Gilchrist]
4. “Open Your Heart” (1986)—True Blue
“Open Your Heart” not only perfectly encapsulates Madonna in the mid-’80s, but the sound of the decade’s pop music as a whole—especially since we’re constantly referencing it. As with “Like A Virgin” and a handful of other tracks before it, the song’s lyrics do what no one does quite like her: express her desires with a knowing, playful wink (she has the lock, and you have the key … it’s about her heart, right).
The fingerprints of its stuttering synthesizer are detectable all over modern hits like Taylor Swift’s “Style” and Ariana Grande’s “Love Me Harder,” and Beyoncé clearly thought her own Fosse-inspired music video was a good idea. But as an explicit influence or something a bit more subconscious, “Open Your Heart” demonstrates that a song doesn’t necessarily need to reinvent the wheel to be hugely influential—sometimes, it can just be really, really good. [Drew Gillis]
3. “Take A Bow” (1994)—Bedtime Stories
Bedtime Stories often feels like one of Madonna’s more consistent and yet frequently forgotten albums; she was drifting away from the house-influenced, sexually charged material on Erotica and hadn’t yet landed at Ray Of Light’s rejuvenating experimentation, temporarily splitting the difference with a collection of songs that feel more like outlier R&B. Co-written by Babyface, who was churning out hits for Whitney Houston, Boyz II Men, and TLC, “Take A Bow” felt simultaneously deeply personal for an artist who in just over a decade had already accomplished so much, and like a skillful capitulation to market forces that were rightfully looking more at black artists for chart toppers.
The risk an artist takes when they make swings as big as Madonna does is alienating fans and offending potential new ones, but the period from Like A Prayer to Bedtime Stories was an especially volatile time for her; it seemed like even she was sick of pushing buttons by the time she started work on the latter album. Superficially, the song serves as a wrap-up for that era of provocation, while also reminding listeners how capable she had become at transforming to meet the music of the moment. In the lyrics, she may be confessing “I’ve always been in love with you,” but she was giving fans yet another reason to reciprocate those feelings. [Todd Gilchrist]
2. “Like A Prayer” (1989)—Like A Prayer
By 1989, Madonna was ready to get real. Following the highly publicized dissolution of her marriage to Sean Penn, the self-professed “fallen Catholic” turned her songwriting toward the heavens with her most ambitious single yet, “Like A Prayer.” The track earned a denunciation from the Pope, and the music video earned her $5 million even after religious groups protested its relationship with soft drink company Pepsi. But even without the blessing of hindsight, “Like A Prayer” symbolized an exciting new phase of Madonna’s artistry.
The bubblegum synths of singles past were accented by church organs, electric guitars, and a gospel choir, while her voice adopted a deeper, more mature timbre. Her classic double-entendres were still there (“I’m down on my knees/I wanna take you there” was of particular contention) but, as Madge started the third decade of her life, “Like A Prayer” proved that she couldn’t only take us to the club—she could also take us to church. [Drew Gillis]
1. “Vogue” (1990)—I’m Breathless
It’s impossible to overstate the impact “Vogue” made in 1990—not just on Madonna’s career, or on pop music, but on popular culture as a whole. At that moment, house music had become synonymous with the gay and underground dance communities, but outside of a few breakouts, like M/A/R/R/S’ “Pump Up The Volume,” it had not substantially infiltrated the pop market. But after just seven years as a recording artist, Madonna was set to release her first greatest hits album, while she tackled a film role as femme fatale Breathless Mahoney opposite bona fide movie star and notorious Hollywood lothario Warren Beatty in Dick Tracy, singing songs by Stephen Sondheim. The film’s soundtrack, I’m Breathless, offered her an unabridged spotlight for the kind of versatility she hoped to showcase, juxtaposing the 1930s glamour of its setting with her own cutting-edge sex appeal. But those songs were not ever going to be pop singles—the kind she was used to releasing, anyway.
Enter Shep Pettibone, a remixer and producer with one foot in the musical communities that Madonna openly loved and was not above borrowing from for her songs. With $5,000 he received from Warner Music, Pettibone quickly recorded a demo whose multitracks she would expeditiously record in a basement studio, for the song’s release as the B-side of her final single from Like A Prayer, “Keep It Together.” Working together on the centerpiece “rap,” a name-check of film stars that again evokes Dick Tracy’s time period but also offers a wishlist for the icons whose ranks Madonna aspired to join, the duo created a tribute to classic Hollywood glamour that presented an effortlessly cool, celebratory, even instructive look at an aspect of gay culture that few outsiders knew well: ballroom.
That she was already working with the stars of the ballroom documentary Paris Is Burning in her music videos and on tour was not necessarily known; but from its musical subtleties (a Salsoul Orchestra sample from a song used about 10 times in Paris, which later led to a lawsuit) to its polished, irresistible house groove, Madonna was catapulting her music into the ’90s and she was bringing LGBT culture with her. Whether or not they knew it was happening, listeners were helpless to resist. “Vogue” captures the past, present, and future of pop all at once, which is why it still sounds just as fresh and exciting now as it did then. [Todd Gilchrist]