40 years of Madonna: The Queen of Pop’s greatest songs, ranked

Four decades after the release of her debut album, we look back at the tracks that define Madonna and redefined pop culture

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40 years of Madonna: The Queen of Pop’s greatest songs, ranked
Center: Madonna circa 2023 (Photo: Ricardo Gomes); Official music video screenshots (Clockwise from top left): “Ray Of Light,” “Take A Bow,” “Cherish,” “Live To Tell,” “Express Yourself,” “Borderline,” “Frozen,” “Open Your Heart” (Screenshots: YouTube).

Madonna delivered her self-titled debut album in the middle of the summer of 1983. Ever since that July day 40 years ago, the undisputed Queen of Pop has been near the epicenter of pop culture, shaping the sound and style of pop music by repurposing outré dance club fashions for a wider audience. “Vogue,” her glamorous house-inspired single from 1990, is perhaps the zenith of this talent, but the music she released before and after that landmark hit are a testament to her status as the most restless and fearless pop artist this side of David Bowie.

Madonna planned to celebrate this momentous occasion by taking her greatest hits out on tour but health problems got in the way. Although her Celebration Tour has been postponed because of her June hospitalization—rescheduled dates are on the horizon—the time remains ripe to celebrate a body of work that’s lost none of its vibrancy, as this list of 40 essential songs attests.

previous arrow39. “What It Feels Like For A Girl” (2000) next arrow
Madonna - What It Feels Like For A Girl (Official Video) [HD]

Based on its sleek veneer and smooth electro-pop rhythms, “What It Feels Like For A Girl” could’ve been an exquisite chill out moment on Music but Madonna constructed the track as an explicitly feminist song. “What It Feels Like For A Girl” isn’t an anthemic rallying call. Rather, it comes from a place of empathy with Madonna exploring distinctly feminine emotions of tenderness and strength. While it’s not quite autobiographical, it’s difficult to imagine Madonna writing “What It Feels Like For A Girl” without going through the emotional journey documented on Ray Of Light: it has a richness and complexity carried over from that spiritual quest.

66 Comments

  • fireupabove-av says:

    I have way too many thoughts on the order of this list to type them all, so I’ll just say “Like a Prayer” should be number one and leave it at that.Also wanted to drop that “Ray of Light” is sort of a cover of “Sepheryn” by British folk duo Curtiss Maldoon

    • samo1415-av says:

      Oh wow, thank you for sharing this fact. I had no idea it was a cover song.Edit:  Loose cover…

      • fireupabove-av says:

        Yeah, it’s definitely different enough but the whole first verse and some of the chorus are basically identical.

    • jek-av says:

      Came here to make the same remark about Like a Prayer, which IMO is Peak Madonna.

  • thepetemurray-darlingbasinauthorithy-av says:

    *opens list for “Frozen”*Ah. Good. Love those 90s Dream Pop vibes. 

  • coolblues-av says:

    No-one who lived through the 80s is putting Vogue at #1. Does this 20-year-old have any conception of how ahead of its time Papa Don’t Preach was. Jeezus. 

    • why8-av says:

      Erlewine, 20s? He wishes.

    • jennyjazz-av says:

      Did you just call longtime respected music journalist (and 50 year old) Stephen Thomas Erlewine a…20 year old?

    • paranoidandroid17-av says:

      Madonna had a one-in-a-generation 1985 on the charts: Like a Virgin, Material Girl, Crazy for You, Into the Groove, Dress You Up. Imagine all those songs being released across different albums and soundtracks over such a short span of time.. we will not see that kind of dominance in our lifetimes with actually good pop music that stands the test of time.

    • sarahmas-av says:

      And Like a Prayer.But I thought about it and I can’t rank her songs. I think I could do like top 5, top 10, top 20 but ranking one by one would change based on my mood.

  • rob1984-av says:

    Solid list. I would like to say that with songs like Like A Virgin and Material Girl, not only did Nile Rodgers produce, he brought in Bernard Edwards and Tony Thompson. Basically it’s the Chic organization backing her up on a bunch of tracks on that album.

  • taco-emoji-av says:

    I will never understand why people feel compelled to rank things like this. Completely tedious activity

    • thepetemurray-darlingbasinauthorithy-av says:

      Google loves it. It think information put in a list is higher-quality than other forms of delivery. This isn’t me taking the piss or anything, that’s literally the reason. 

    • marty-funkhouser-av says:

      Because it can lead to mostly fun conversations? When The Avocado did a Madonna Song Tournament hundreds of Madonna fans to to share memories and favorite songs and what Madonna means to them. It was all fun and harmless. Stepping off your lawn now … 

    • bcfred2-av says:

      Because it gives music fans something fun to bounce around with?  

    • ninjabandit-av says:

      No to mention the scandalous omission of Hanky Panky

    • fuckyou113245352-av says:

      I will never understand why people click on shit and comment on content they know they won’t like before they click it.  You must be retarded.

  • bs-leblanc-av says:

    Maybe it’s because I was watching A League of Their Own recently, but I’m a bit surprised “This Used to Be My Playground” isn’t on here.

    • draculamountain-av says:

      Great tune!

    • paezdishpencer-av says:

      Same….its got a great haunting melancholic melody and I would honestly argue it was one of her best ballads. Happy to see Beautiful Stranger on here. I thought it was a fun song that really fit Madonna well at that time plus she seems to be having the time of her life in the video playing up against Mike Myers….they always seem to enjoy each others company (her SNL send up of Truth or Dare with Mike as Wayne Campbell can still crack me up “Look at the unit on that guy!”)

    • ninjabandit-av says:

      It’s omission tells you a lot about this bogus list

  • marty-funkhouser-av says:

    The Avocado did a Madonna Song tournament. Without resorting to a slide show, the top four were:4. Ray of Light
    3. Into the Groove
    2. Express Yourself
    1. Like a Prayer

    • sarahmas-av says:

      I really appreciate Don’t Tell Me ranked as high as it is on this one though. My fave song on that album, I played it obsessively

    • ol-whatsername-av says:

      I didn’t love “Vogue” at the time, particularly, but I love it now. I am a little shocked that I know all the words.Having said that, I’d probably go with “Express Yourself” as the best (the single version, not the album version). What a fantastic song, in all ways.

  • cosmicghostrider-av says:

    Everywhere else: *has recap of Secret Invasion finale posted already*
    AV CLUB: this is the one time a show premiere’s at 3am that we don’t have a review ready first thing the next morning.

    I will be going elsewhere to find out what happens on that boring boring but possibly mandatory MCU show thank you.

    • thepetemurray-darlingbasinauthorithy-av says:

      I thought you didn’t have to watch the shows to understand what goes on in the MCU? 

  • SpaceyKacie-av says:

    I think “Die Another Day” doesn’t get enough love

    • thepetemurray-darlingbasinauthorithy-av says:

      Ah, yeah, see, this is a list of songs by Madonna, the pop start from Detroit, Michigan. USA.“Die Another Day” was performed by Madonna “Madge” Chittingshelm-Smythe-Smythington-Ritchie, who is a proper, authentic, Brrrrrrritish ladeh, with mahogany cabinets filled with fine bone china and crumpets and corgis and such.

  • fuckyou113245352-av says:

    vogue ain’t what it used to be.

    • bcfred2-av says:

      She wanted Katherine Helmond’s results, and instead got those of the friend who had complications with her complications.  

  • recalcitrant-doogooder-av says:

    Who?

  • mikolesquiz-av says:

    Doing a Top 40 Greatest Madonna Tracks seems wildly ambitious. I think we can limit her Best Of to a single disc and that’s plenty by any measure.

    • paranoidandroid17-av says:

      A collection that’s, in a sense, immaculate.

    • michaeljc-av says:

      I had a hard time narrowing all of her hits down to 40! She has so many amazing songs.

    • buckfay-av says:

      I assume that disk is a 45? I can’t think of one song of hers I liked, let alone, two, but I’m feeling generous.  I honestly believe she has the weakest and least pleasant voice of any popular singer ever.

      • allisonkj-av says:

        Why are you even here? I will never understand people who pipe up on posts just to say “This thing that a lot of people love and is wildly hailed by critics? I just want you to know that I personally don’t care for it.” No one cares.

    • ohnoray-av says:

      nah, even this list made me realize it’s insane how much I know of her discography. true legend.

  • rayoso-av says:

    It’s a crime that “Angel”, “Dress You Up”, and “Who’s That Girl?” were left off of “The Immaculate Collection”.

  • blpppt-av says:

    I friggin love that bouncy melody in “Who’s That Girl”. Also there’s something about that 80s synth riff in “Live to Tell” that hits me with strong nostalgia. Like “Sunset Grill” and the synth horns.Some things just instantly take you back to the 80s, lol.Edit: Oh, and as for “Material Girl” — Steve forgot to give credit to that simple but very groovy drum work to the late great Tony Thompson.

    • jomahuan-av says:

      i was a dumb 9-year-old and that damn synth on ‘live to tell’ used to make me cry.
      also, give it up for ‘causing a commotion,’ which is basically ‘into the groove, part 2.’

  • carltonmackenzie-av says:

    God she sucks.

  • evanwaters-av says:

    While I like a lot of her later stuff I still think “Borderline” has something about it that just puts it at the top, or near enough to it. Just the way the chorus goes is so unusual that it sticks in your head forever, and it nicely reflects the singer’s mixed feelings.(I also really like “Voices” off of Hard Candy.)

    • bcfred2-av says:

      Her voice was still pretty thin and nasally in most of those early hits, even if they were catchy and fun. I think many people felt she was a MTV product until proving herself with bona fide radio hits.

  • seven-deuce-av says:

    “What it Feels Like for a Girl” is waaaay too low.“Vogue” may be the most overrated song she ever wrote.That is all.

  • knukulele-av says:

    She would have been forgotten long ago if not for that sweet sweet Weird Al Yankovic bump.

    • hanssprungfeld-av says:

      Yeah, but the way she assassinated him at an awards show left a bad taste in my mouth. Surprised she hasn’t caught more heat for that, tbh.

  • bhlam-22-av says:

    I always found “Borderline” and “Material Girl.” kinda overrated. Would put “Hung Up” and “Lucky Star” higher. Kinda mean to MDNA and Rebel Heart that nothing shows up from them. Putting “Vogue” at number one? I mean, if you want. It’s great. Not my pick. A little rude to shut out I’m Breathless otherwise. It’s goofy, but there are good tracks. Otherwise, it’s hard to argue with a list of great songs from one of the most prolific pop artists ever. 

  • danniellabee-av says:

    Like a Prayer at #5? Blasphemy! In my heart it is #1. 

  • shark73-av says:

    The only post-1990 Madonna song I’ve loved was “Beautiful Stranger,” but I hate electronica and club music, so it makes sense that I stopped paying attention to her when I was a sophomore in high school. However, those early days when I was a child and she was a young adult and Bette Midler introduced her at LiveAid… great days. I still play the first three albums a lot.

  • bgunderson-av says:

    None of these are Diana Ross songs. Perhaps you misunderstood the assignment.

  • theotherglorbgorb-av says:

    Madonna always struck me as the type to push boundaries just for the notoriety. As in she actively sought it. She was never subversive, just obvious. I guess it’s good that she still has a music career, but has she been relevant in a couple of decades?And then there was this:
    https://uproxx.com/tv/madonna-jimmy-fallon-the-tonight-show-history/

  • bcfred2-av says:

    Surprised to see Cherish so low – I’d rank it above at least half the songs ahead of it.

  • peterbread-av says:

    The video from Guy Pratt talking about how he came up with the bassline from Like A Prayer is worth a watch.

  • jackstark211-av says:

    How in the hell was this song not on the list.

  • jhhmumbles-av says:

    I used to like her early stuff, like Borderline.  But when she got on that Papa Don’t Preach phase I tuned out. 

    • ol-whatsername-av says:

      That was it, huh? That “phase”? What about the 75oo “phases” that followed? It’s MADONNA, after all – she was multitudes!

      • jhhmumbles-av says:

        I wouldn’t know because I die offscreen. But somehow my one comment here tells you everything you need to know about me.

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  • alanlacerra-av says:

    Checks to see where “Frozen” falls on list. High, but not high enough. Close, though.

  • alanlacerra-av says:

    No love for “Where Life Begins”?

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