Get into the groove: ranking Madonna’s #1 songs

From "Like A Virgin" to "Take A Bow," The A.V. Club commemorates the Queen of Pop's new greatest hits package by choosing which tracks are, well, the greatest

Music Features Songs
Get into the groove: ranking Madonna’s #1 songs
(from left) Madonna in photo shoots for the promotion of Ray Of Light; The Immaculate Collection; Madonna; Erotica; and Live To Tell. (Warner Music) Image: Todd Gilchrist/ Frank Micelotta; Herb Ritts; George Holz; Fabien Baron; Herb Ritts.

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.

previous arrow12. “This Used To Be My Playground” (1992)—A League Of Their Own Soundtrack next arrow
Madonna - This Used To Be My Playground (Official Video)

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]

44 Comments

  • yllehs-av says:

    Well, there’s maybe 4 songs on there that wouldn’t make me want to stab out my ear drums.  Thanks for nothing, Madonna.

  • maulkeating-av says:

    No “Frozen”? It was number one in the UK, Finland, Greece, Hungary, Italy, Scotland, and Spain.And I reiterate my call to bring back 90s dream pop, dammit.

  • ohnoray-av says:

    Madonna has done some problematic shit, but idk, seems inevitable when you have literally been in the public eye for so many decade. Girl really had a huge impact not just on music (for the better), and on celebrity (for better or worse).

  • filthyzinester-av says:

    Someone get word to Madonna, The SPR3 are down to collaborate!

  • hootiehoo2-av says:

    I’m 48 and if Like a prayer wasn’t top 2 I was going to find Todd and beat his ass! :)Vogue is so bland and overbearing but it was a monster hit.Fuck my 2nd favorite Madonna song is La Isla Bonita, which never made it to #1.

    • bcfred2-av says:

      I was likewise surprised Ray of Light never hit #1. Probably my favorite of hers.

    • jek-av says:

      I feel exactly the same way; as soon as I saw the article title, I came looking for Like a Prayer.Like a Prayer is peak Madonna.

      • wombat23-av says:

        its definitely where they seem to have the best handle on her voice. she sounds really great and clean in the song in a way that other songs dont seem to get. like they had exactly her range and the recording guys nailed it hard. its unquestionably a peak for her.

        • jek-av says:

          Agreed. And she comes through with raw emotion in a way that she doesn’t in other songs.Life is a mystery.

    • jomahuan-av says:

      my favourite is ‘angel’ and that’s like a side B tune.

    • charliedesertly-av says:

      Yep, Vogue is overrated as fuck

  • cariocalondoner-av says:

    Even without … 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 …Urgh – just – what was the point of this sentence? Of all the … why bring up Gaga at all? Of all the many different examples one could choose to show Madonna’s made an ‘irrefutable impact on music’ or on ‘pop culture’ (since the Britney/Xtina kiss was mentioned), I’m puzzled why the similarity between one hit song of hers and another by someone else done decades later, got a mention as one of two stand-out moments of hers.

  • drew8mr-av says:

    So, I put together a playlist for the wife a couple years back “Bitch, I’m Madonna A Sides 1982 – 2020″. That was every A side (no dupes, remixes, just one version of each) I could find and it has 91 tracks.  50 number ones out of 91 is pretty fucking decent.

  • thomheil-av says:

    Good to be reminded that the best songs aren’t always the most popular songs. Nice to see “Open Your Heart” gets its due, though — a great pop song that (in my mind) serves as a proto-“Express Yourself,” which we all know is the best pop song ever created.

  • fireupabove-av says:

    True Blue is a near perfect album – coulda done without “White Heat” but the rest of it is a delight. And yet, she didn’t rest on those wildly successful laurels and just pushed into whatever new territory she wanted to. Like a Prayer – brilliant. Erotica – brilliant. Ray of Light – brilliant, and each of these albums is a real departure from what came before for her.I think my top 3 would be “Live to Tell”, “Like a Prayer”, “Ray of Light” (not a #1 somehow!), but with so much good to choose from it’s hard to be too mad about any order.

  • dontdowhatdonnydontdoes-av says:

    The impact Madonna had for me growing up. her first album will always make me think of my mom blasting that CD when my dad got her a Chevy Blazer with a CD player, the music videos she made ( lets not forget she had Danny Ailleo play her dad, getting Chris Cunningham to do the Frozen video, introducing me to Sasha Baron Cohen (Ali G) ), and an endless list of stuff.but i swear growing up watching A League of Their Own playing on cable constantly, I don’t remember that Playground song, much less that it was number 1. who know coming into a Madonna number 1s article I would learn something new and “discover” a new song.

  • magpie187-av says:

    Like a Prayer, Crazy for You, Live to Tell are my top 3. Madonna was at her peak when I was in high School 86-90. Great time in pop culture to be a kid.

  • drewskiusa-av says:

    As a proud and dedicated member of her harem (The Gays), I can vouch that the Queen of Pop truly has enough hits to fill at least 3 concerts in a row, each with unique and individual songs from her library of hits. Her net worth is over $800 million and she earned every penny of that with her shrewd and perfection-laden choices of song writers, producers and hell, even her back-up dancers who are THE BEST IN THE BUSINESS (have you seen them roller-skate?!)Long live the fucking queen! 😀

  • blpppt-av says:

    I’m most often referred to as a metalhead, but I’ll be damned if I don’t find myself getting a 2nd appreciation for 80s pop as I go back through Youtube. They really had some clever ways of putting together melodies. Like the insanely catchy “Who’s That Girl”—-and oh man, Madonna is like 10x hotter as a brunette.Its funny, as the synthesizer technology has advanced over the past 3-4 decades, it has lost a lot of its charm—-you can tell that the synthesizers in 80s pop aren’t real instruments, but their inability to nearly perfectly emulate those instruments basically creates a whole new instrument which seems to be missing with today’s superfast processors/dsps that can come very close to perfect (if somewhat lifeless) emulation.Oh yeah, and you darned kids, get off my lawn!

    • evanwaters-av says:

      My general view is the best synth music isn’t trying to sound like real instruments most of the time. 

    • milligna000-av says:

      What nonsense. As if the past few decades hasn’t been full of going BACK to analog synths.

      • blpppt-av says:

        Nonsense? In the 80s, you got that sound because you HAD to—the technology didn’t exist to perfectly emulate an instrument, and you shaped your songwriting around it.Its quite different when you have the tech readily available to nearly perfectly emulate the sound of the instrument. That limitation disappears. Not to mention with today’s powerful computers, you don’t even need to touch a key on a synthesizer if you don’t want to.

  • seven-deuce-av says:

    “Rain” should have hit #1. Underrated track and probably my favourite Madonna song.

  • cab1701-av says:

    I just wanna say thank you for posting this. I’m a ride or die Madge fan. Have been most of my 48 years. Her music has been (and continues to be) the soundtrack of my life. LONG LIVE the QUEEN!

  • mikepencenonethericher-av says:

    Out of this list I’d vote for “Open Your Heart”.For the ones that didn’t make it to #1, “Cherish” and “Ray of Light”

  • erictan04-av says:

    Turns out I stopped listening to Madonna around the time she did that song with Justin Timberlake, so I’m definitely not familiar with anything after that collaboration, and it’s a lot of songs that did well, apparently.I still like many of her earlier 80s and 90s hits and I’ll stick to those.In any case, Congratulations, Madonna!

  • memo2self-av says:

    If you’ve got ten minutes and some imagination, the brilliant jazz guitarist Bill Frisell covered “Live to Tell,” and I always point to this single track to introduce newbies to his work.

  • hulk6785-av says:

    “Like A Prayer” at Number 2!!!!?  C’MON!!!!

  • graymangames-av says:

    Not even close to a Number One, but can we give it up for that one time Madonna and Massive Attack covered Marvin Gaye?

    • risingson2-av says:

      Oh it’s my boyfriends’ favourite so he mentions it whenever someone speaks the name of Madonna. To me it irritates me a bit as it is just another Craig Armstrong arpeggio heavy dramatic arrangement and just another trip hop orchestral number like the ones from portishead, silent poets, hooverphonic, bergman, etc. Or maybe because I switched from big fan of Craig Armstrong to be big meh.

  • risingson2-av says:

    I am a huge fan of Madonna’s power ballads, so I am quite satisfied that half of “Something to Remember” is here – “Crazy For You” is one of the better songs to sing in the car with the windows down.Still, ballads are the best part of “Music”. “What it feels like for a girl” followed by “Paradise” is an incredible combo. And I also miss Madonna’s lullabies: “Dear Jessie” and “Little Star”. I don’t know why I am so touched by motherly Madonna. 

    • heasydragon-av says:

      I love the story of how she came to record “Dear Jessie”  – her producer was late coming to the studio because he was picking up his daughter – the titular Jessie – from school, Madge was pissed at him but struck up a friendship with his daughter and the producer offered her a song he’d written for his daughter upon seeing how much fun they were having together. The single cover has a bit of Madge-history attached to it as well. It’s the cover with Madonna in bed with the Minnie Mouse ears making a face. The picture was taken by the late (and forever great) Herb Ritts and was a dig at Madonna’s early critics who called her “Minnie Mouse on helium”.

  • petechicagolondon81-av says:

    I’m a fan of Madonna, but saying she’s a “trailblazer rather than a copycat” on the “This Used to be My Playground” entry (a fantastic song, btw), is a bit funny and inaccurate, as she and her music video director *stole* the video, nearly frame-by-frame from an obscure Boy George video, “To Be Reborn.”
    Madonna is a trailblazer and an original, but not above swiping when necessary (listen to “Vogue” and then listen to Malcolm McLaren and Willi Ninji’s “Deep in Vogue”)

  • wrightstuff76-av says:

    Into The Groove never made #1 on Billboard, that’s surprising.It’s her biggest seller over here in UK, even after her late 90’s renaissance that started with Ray of Light.

    Also it’s weird to think that Who’s That Girl is considered a song only hardcore Madonna fans would remember. I was pissed that the song wasn’t included on the Immaculate Collection, that I actively bought WTG soundtrack.

  • icehippo73-av says:

    “Live to Tell” and “Like a Prayer” are #1 and #2. There should be no argument there. 

  • mordecaiclevername-av says:

    I don’t care much for Madonna’s music. I’m not slamming her or anything—I’m just not a pop music guy, so her work doesn’t vibe with me.With that said, goddamn Like a Prayer is such a good song. (I’m a sucker for gospel choirs, which is funny because I’m not religious.)Credit where credit’s due, Madonna has one other song that I like: Beautiful Stranger, an impressive feat given the first time I heard it was watching the video which was nothing more than a glorified trailer for the second Austin Powers movie.

  • butterflybaby-av says:

    The curve was lowered as soon as she showed that below average face.

  • pcxl-av says:

    I feel like Danny Aiello deserves an honorable mention for his follow-up response song to “Papa Don’t Preach” entitled “ Papa Wants The Best For You.”The video has him emotionally wandering the city, looking for his daughter Madonna.(We also need an inventory roundup on response songs)

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