My Madonna Top 20 Countdown

Madonna has one of the most impressive catalogues in all of pop music. She has more top 10 hits than the Beatles! Let that sink in for a minute. Her career as a pop star is longer than most besides someone like Cher. That said, Madonna has had a much more consistent presence on radio and the charts than Cher who seems to go through cycles of popularity and switches back and forth between movies and music much more easily than Madonna. True some of Madonna's more recent material isn't among her best work but it has its merits too. At this point its kind of thrilling to see just how far she is able to go as a female pop star in an industry that thinks of female pop stars as disposable after a certain age. Also comparing music off Ray of Light to that of Like a Virgin is tricky because while they are both pop music they are very different forms of pop music made at very different times in both Madonna's career and pop culture as a whole.

Overall my general thinking for Madonna is that the 80s was her best decade for singles, the 90s was her best decade for albums, the 00s is hit or miss with some real high points and some real low points and the 10s is mostly consistent but doesn't reach the highs of her previous decades. There are exceptions to this line of thinking of course but that's generally how I view her career.

All this is to say that at just 20 songs there is a lot music not here that I love. There's really no deep cuts here either which makes me think I may do a second countdown of my favorite deep cuts by Madonna at some point down the road. She is one of those artists that I am completely and utterly invested in where I do listen to all her music and digest the whole albums as they come out. So these 20 songs are the ones that I seem to go back to the most for the past 22 years as well as the songs that shaped my taste and perception of pop music as a whole. These songs are the ones I'm always ready to hear no matter what mood I am in and that really showcase why I love her and why I think she is the best female pop singer of the past 4 decades. She may not have the strongest voice but she has the strongest personality and drive which I think is sometimes more important to pop music then just being able to sing well. Madonna's music is also among the most timeless for this kind of pop music and is still extremely influential. All the pop girls of the past 30 years owe some sort of debt to Madonna. Because Madonna was there right at the start of the music video age she set the template for all other female pop stars to follow (much like Michael Jackson did for all male pop stars.) As a result she remains THE key figure for pop music since the early 80s and until there is another massive shift in pop music that goes beyond music videos she will remain the touchstone for female pop stars.

Anyway as always this is just my opinion and not a definitive ranking. Still I feel that if you don't like anything off this list chances are you don't like pop music.

20. Material Girl

The song that haunted Madonna for years to the point that she didn't like it anymore. Every newspaper and magazine would refer to her as The Material Girl for years. It's only been in the last decade or so that she seems to be ok with it again. The song is interesting in that it shows Madonna is not a woman who gets used by men, instead she's the one who uses the men. Many people thought the song's celebration of materialism and treating men as disposable was offensive and anti feminist despite the fact that male musicians have delivered the exact same message since the beginning of pop music and continue to do so to this day. Of course as a young boy I just loved how catchy and girly the song was and I loved her pink Marilyn Monroe dress in the music video too. At the end of the day it's just a pop song that's fun to listen to and has a bit of wish fulfillment that's always been one of the biggest appeals of pop music.

19. Die Another Day

A lot of people think this is the worst Bond theme of all time. Those who say that obviously have not heard Another Way to Die by Jack White and Alicia Keys and have forgotten about the Man with The Golden Gun by Lulu. I can see why as a bond theme that this is divisive but I really love it. It's Music era Madonna meets James Bond where the weird synths and beats meet dramatic string flourishes that I feel juxtapose against each other quite well. The overall song feels like it's being propelled by a real sense of urgency and danger which makes it compelling for me as a listener. Also for what it's worth both my husband and my Dad love this song so there's that.

18. Music

Madonna's first # 1 since Take a Bow and her last #1 hit in the U.S. Music once again saw Madonna on the cutting edge even as she was entering her 3rd decade as a pop star. The production by Mirwais sounded like nothing else on the radio at the time. There's a reason this shot ahead of Britney Spears’ Lucky and Christina Aguilera's Come On Over in the fall of 2000 (Britney was dominating at this time but her music felt of the times because it was all created by Max Martin who seemed to be writing and producing all the big hits at that time. It would be a few more years before Britney was leading the pack in terms of innovation.) Music is another example of how Madonna can be ahead of the times while still tapping into the zeitgeist of the times. Also I love music video where Madonna flips the bravado of hip-hop on it's head and creates a ladies night out to remember.

17. Like a Virgin

Seeing the music video of Madonna dancing around a gondola in Venice connected with me instantly when I first saw this Like a Virgin in the fall of 1997. I was over at a friend's house and we were watching a special on Weird Al because my friend was a fan of his. MTV was playing all his videos, but before his videos they would play the original music video he parodied. As soon as Like a Virgin finished I needed to own it. I was buying what Madonna was selling hook, line and sinker. It's a pop song that is both familiar (with a melody borrowed from a Four Tops song) and progressive with the way Madonna brought the word Virgin to the pop charts and had the gusto to not only be sexy but own that sexiness. Her performance at the 1984 MTV Video Music Awards was controversial because Madonna was exuding sexiness in a way that good girls were not supposed to do unlike men such as Mick Jagger, Rod Stewart or Prince who are allowed to be sexually explicit. Like a Virgin is so iconic as a song now that just saying the word Virgin elicits this song for most people. When I saw Myylo one of the opening acts made a joke about something being a first at a concert, which led to the singer saying quickly "Like a Virgin!" The song itself is so iconic it's practically short hand now. Like a Virgin taps into the Madonna mythos beautifully because it's not just a pop song by a woman who owns her sexuality and freedom, it also elicited a sexual awakening for an entire generation of girls (and gays!) and would continue to do so for years to come. I didn't know what the word virgin meant yet at age 11 and I wasn't completely sure how sex worked either, but I knew I was different from the other boys and I didn't have any role models to look up to yet. As soon as I saw Like a Virgin I had a mini awakening. Here was someone who had a lot to teach me about sex and about being feminine while still not conforming to society's standards or what other boys wanted you to be. That's what made Madonna's music so powerful because it empowered those who did not fit into society's strict rules of binary relationships. At 11 I realized I had a lot to learn from this women and I never looked back.

16. Cherish

Cherish feels like the last time Madonna made a really cute pop song just for the sake of it. Something she did quit often throughout the 80s but as the 90s dawned she would head into more mature territory. There's not much to say about this one other than it's a perfect pop song that makes you feel good while you are listening to it which is why I listen to it so much. The hunky mermen in the music video are an added benefit too ;).

15. Don't Tell Me

This was a song that didn't click with me until it was released as a single but after that it soon became one of my favorites. It's a really interesting song because it doesn't sound like anything else I have ever really heard. We have a little country here, a little bit of strings there, some subtle dance beats and a melody that worms it's way into your brain slowly but surely. It's a slow burn type of song that doesn't seem like much at first but reveals itself as a great pop song the more you listen to it. Again even in 2000 Madonna was still making pop music for the masses that didn't conform to what else was on the radio.

14. Like A Prayer

When I first heard this one the radio Thanksgiving weekend 1997 I was swept up immediately. The song has a real sense of drama and scope to it that makes it feel grander and more ambitious than most pop songs. There's a reason it has so much religious imagery and iconography in the lyrics and that's because listening to Like a Prayer feels like a religious experience even though it's not. The music video of course drove home the religious imagery to the point of controversy and backlash. What gets forgotten though when discussing the music video for Like a Prayer is that it's about racism in America. It's about how black men are mistreated and blamed for crimes they didn't commit. It's about Madonna turning to faith to do what is right and help free a black man from a murder he didn't commit. It's a song that feels like Madonna's most timeless with a video that 30 years later still says a lot about institutionalized racism in America.

13. Deeper and Deeper

This is one of Madonna's most underrated singles. Yes it hit the top 10 in the fall of 1992, but following up the Erotica single and coffee table book Sex gave it a disadvantage as people began to really turn against Madonna more than they had before. As result this seems to be a top 10 Madonna hit only her diehard fans remember. It's a brilliant dance song with some smashing Spanish flamingo guitar and early 90s house piano. It feels like the conclusion of the Shep Pettibone Trilogy which began with his remix of Express Yourself, peaked on Vogue and concludes here. She even does a call back to Vogue at the end which is intentional. Vogue celebrated a dance made popular in the gays discos around that time. Deeper and Deeper is about a young gay man who has struggled with his sexuality, but is finally coming to terms with it through the love of another man. That went over my head when I was 12, but now it feels like a powerful statement about overcoming internalized homophobia and learning to live your life free and open as a gay man. Knowing what the song is about now makes these lyrics hit even harder for me:

"Someone said that romance was dead
And I believed it instead of remembering
What my mama told me
Let my father mold me
Then you tried to hold me
You remind me what they said
This feeling inside
I can't explain
But my love is alive
And I'm never gonna hide it again."

This also explains why the music video is the only one where Madonna doesn't lip sync because it's not about her it's about the gay community. The video celebrates the gay community most in the middle when Madonna goes to a gay disco to dance and we see a representation of people across races, genders and sexualities. At a time when being gay was not being celebrated in most pop music and the AIDS crisis was at its peak Madonna was giving the community a platform and visibility that was being denied to them at the time.

12. Dress You Up

For years Dress You up was kind of forgotten despite being a top 5 hit in 1985 and there's a few reason for that. First is that the previous singles off Like a Virgin were era defining songs that solidified Madonna's status as THE female pop icon of the 80s and Dress You Up couldn't compete with that. On top of the Like a Virgin singles Madonna was also dropping soundtrack songs that were blowing up too such as Crazy for You and Into the Groove. The Dress You Up music video is also just taken from the opening of the Virgin Tour, which was also available to purchase on video around that time so it doesn't have an iconic music video in all honesty. I think the biggest reason though is because it was left off the Immaculate Collection. That greatest hits is both incredible and frustrating. Incredible because having all those Madonna hits stacked together shows how impressive her run was in the 80s. Yet at the same time it's incredibly frustrating because not only are most of the songs edited and remixed into inferior versions from their original album mixes, but some of Madonna's biggest hits are left off as well. That collection kind of defined the Madonna cannon for years, especially when CDs ruled the world. I strongly believe radio stations and jukeboxes filled their Madonna quota by just having The Immaculate Collection CD. So the songs not on The Immaculate Collection ended being forgotten for a while during the 90s and 00s. Now in the streaming age and radio that is nostalgic for 80s music more than ever Dress You Up has made a mini comeback. I now hear it on the radio, it got included on her 2009 greatest hits Celebration and overall it seems to have taken it's place among her greatest 80s hits. That guitar solo rocks btw!

11. Lucky Star

Madonna's self-titled debut is Madonna at her most accessible. Before the controversy and button pushing she just cut one of the best dance records of the decade. The singles from this album are beloved by people of all ages including those who don't really like Madonna because those singles are just so likable. Lucky Star was played at my wedding and it filled up the dance floor. It's really one of the best pop songs ever written, simple yet exciting at the same time. The key changes throughout the song keep you on your toes but it's always danceable, easy to sing along to and most importantly fun. I also remember trying to dance along with the music video choreography too when I was younger. The dancing in this video is just complex enough to be interesting but simple enough for 12 year old me to follow along in my bedroom. I did a lot of double kicks into the air in my bedroom with the door closed when I was in middle school.

10. Hung Up

American Life is an album I didn't care for at the time but have grown to appreciate over the years. Still there's no denying that Madonna's career took a huge hit because of the commercial failure of that album and she never really fully recovered. Madonna knew she had to come back strong in order to get back on to the charts and the resulting album Confessions on a Dancefloor turned out to be a late career mini peak that briefly made Madonna the queen of the dance floor one more time. Hung Up might be Madonna's last truly transcendent single. She had many good songs ahead of her but this feels like the last real classic from her. Hung Up is the last time she made a song worthy of being compared to past triumphs like Into the Groove and Vogue. I also just remember hearing it with my friend Mallory for the first time in her dorm and we were so giddy about how good it was. I remember Mallory clapping her hands and saying "Yay Madonna!" I remember introducing it to my friend Brandon who quickly fell in love with Madonna. I remember dancing to it and the other songs off Confessions at the bars and gay clubs after I first came out and started going to such things. It stayed on the dance charts and was played at the gay clubs for almost 2 years and it was completely warranted. I couldn't have asked for a better song to soundtrack my coming out party!

9. Burning Up

From the moment I first saw this music video on MTV I loved Burning Up. The combination of that throbbing synth line with the heavy metal guitar makes for one of Madonna's most electric and addictive dance numbers in her entire catalogue. Also as her first music video for MTV (She had a video for Everybody but Burning Up was the first video sent to the network) it couldn't have been a better introduction. As Madonna dances and gyrates in the middle of the road she sings "Unlike the others I'll do anything! I have no shame I'm on FIRE!" With those lyrics Madonna announced who she was and what her mission statement was going to be for the rest of her career. Pop music was never the same again!

8. Live to Tell

Live to Tell is a pivotal moment in Madonna's career. Up until this point despite all the success she had seen in 1984/1985 people were convinced Madonna was never gonna last (much like Britney Spears). People thought Madonna was just a pop tart with no soul and that Cyndi Lauper was going to be the pop star to go the distance. Then Live to Tell came out and people started reassessing their view on the once and future Queen of pop music. This was the first time Madonna showed there were not only more layers to her than people originally thought but it was also their first glimpse at Madonna the shape shifter who's image, music and presentation was going to change with the times. Live to Tell has a dark but compelling sense of drama and storytelling to it and that is conveyed perfectly through Madonna's singing which got a little deeper and more soulful here. All of a sudden it was clear Madonna could get more serious when she wanted and be a compelling storyteller as well. Live to Tell is the moment Madonna went from being a huge pop star to THE pop star of the MTV era. Also I love the production flourishes during the bridge which add to the sense of drama and darkness this song perfectly exudes. This song can give me goosebumps if I'm in a certain mood.

7. Take a Bow

Madonna's longest running U.S. #1 (7 weeks) was also used in the season 1 finale of Friends and won her best female video at the 1995 MTV video music awards. Like Live to Tell Madonna is in storytelling mode with Take a Bow. She conveys the sadness and heartbreak of this song perfectly. Yes she can't sing like Mariah or Whitney but she doesn't need to. This song feels more emotional because of her more limited vocals and the sadness Madonna conveys through her voice throughout the entire running time is devastating as it is beautiful. Babyface was the hot songwriter/producer of the moment in the mid 90s and this just might be his peak. The back and forth between Madonna's vocals and Babyface's are lovely. The music video meanwhile is one of her best and helped Madonna snag the lead in Evita. Few ballads have been as beautifully sad as Take a Bow.

6. Secret

Bedtime Stories the album sometimes gets lost between Eroctica and Evita/Ray of Light but it might just be my favorite Madonna album of all time. It's her most seductive and cohesive album in her whole career and it features some quiet moments of brilliance like the lead single Secret. It's one of Madonna's most stripped down performances featuring a bluesy guitar, drums and subtle use of strings but it works wonders proving Madonna can hold down a song without tons of production swirling around her. Whoever plays guitar on this btw is really good.

5. Open Your Heart

This is a pop song that starts at 11 and just goes up from there. This is the opposite of Secret. From the start we hear a drum machine that is turned up to the limit and those synths throb and sparkle all over the place. Nothing deep is going on here from a lyrical standpoint and that's OK because Open Your Heart is all about the sugar rush great pop music delivers when it's firing on all cylinders. And oh yeah the boy in this video who wishes he could dance like Madonna that was totally me at that age. When he gets to dance off into the sunrise with Madonna who is now just his best pal, let me tell you that was every gay boy’s dream! I know it was mine.

4. Into the Groove

Into the Groove is a celebration of dancing and pop music that has few peers. Into the Groove captures the thrill and giddy high pop music can give you when you let yourself be taken over by music as attractive as this. It captures everything we love about Madonna and pop music in general. For most pop stars this would be their one crowning achievement but for Madonna this was just another day at the office. Also another Madonna song that filled up the dance floor at my wedding.

3. Beautiful Stranger

Ray of Light is a great album but I don't find myself reaching for the individual songs much. It works best as a complete experience. That said I like it more as an adult than I did when it first came out. It was Madonna so I liked it back in 1998, but it was much more adult and serious than what 12 year me was ready for. I wanted more songs like Burning Up and Open Your Heart.

Enter Beautiful Stranger.

Produced and co-written with William Orbit, who was the mastermind behind Ray of Light, it feels so much lighter and more fun than everything on that record except maybe the title track. I loved Beautiful Stranger the moment I first I watched the world premiere on TRL back in 1999. It was a just a great pop song that gave you a sugar rush like her 80s hits. Also all my straight guy friends liked it thanks to the Austin Powers connection so I could listen to it around them with no shame. The music video, which features Mike Myers as Austin Powers, is also wonderfully hilarious and fun. As I became a bigger fan of the 60s I learned to the love the song more for all the ways it recalls the 60s while still feeling modern. I especially love that 60s flavored flute that plays at the end. This was my favorite Madonna song that I got to experience in real time and it's still a bop 20 year later.

2. Express Yourself

This is Madonna's best feminist statement where she tells girls that it doesn't matter how much money or material possessions their guy has, if he doesn't treat them right he's not worth it. It's the opposite of Material Girl but only Madonna could make both songs sound like feminist statements. It's also one of her best pop songs, which features one of her most soulful and energetic vocal deliveries. In fact Express Yourself is always the highlight of any concert she does because she goes all out with both her dancing and singing. While it's hard to pick a favorite the Girlie Show performance gets my vote because it might be my favorite Madonna performance ever. She is on fire throughout that performance of Express Yourself. I used to watch this performance over and over again on my VHS copy of the Girlie Show: Live Down Under. Skip ahead to the 1:00 minute mark in this YouTube video because that’s where Express Yourself begins.

The music video directed by David Fincher is also another career peak. It's an updated adaptation of Fritz Lang's Metropolis and it is a wonder to behold. It truly feels like a mini film. I also remember practicing the choreography where she comes out in the blue power suit and grabs her "crotch" at the end. I loved the energy and androgyny of that moment. Years later I remember in college I took a course called the history of the future where we learned how people looked at the future and what that said about those times. We watched parts of Metropolis and I was able to convince my teacher to play the music video of Express Yourself in class off my video cassette of the Immaculate Collection I had owned since I was 12. Also as cheesy as it sounds I thought of this song too when I broke up with my first long term boyfriend. I realized he showered me with gifts and praise without actually treating me as a person with wants and needs and I realized he was not the big strong hand I needed. For my wedding I asked the DJ if he could find a mash up of Express Yourself and Born This Way and to his immense credit he did! I was able to dance to a song that now represented feminism and gay rights and it was wonderful.

1. Vogue

When I think of Madonna the year & image I think of first is 1990 when Madonna had the Dick Tracy Hollywood glam look and the cone bra & pony tail look from the Blonde Ambition Tour. It feels like peak Madonna at her most iconic and glamorous and in the middle of all that there is Vogue. It is both a celebration of classic Hollywood and Gay Culture that remains a high water mark for not just Madonna but for pop music in general. Voguing came from the gay discos and ballroom scenes. It's a form of dancing that gives gay man strength and power through beauty and movement in a world that wants to tear us down constantly. While most of the mainstream think of Vogue as a dance fad it's still a huge part of the gay ballroom scene which is why Vogue endures. Other songs from 1990 have been forgotten but not Vogue. Up and coming pop stars, especially gay ones like Troye Sivan, still put this on their pride playlists because it's still an anthem that resonates with our community. There’s a reason that the second season of Pose, which takes place in 1990, revolves around the success of Vogue that year.

The music video was also a celebration of Queer culture featuring mostly gay back up dancers who would eventually join Madonna on her Blonde Ambition tour and would be immortalized in the documentary film Truth or Dare. Yet, Vogue taps into the more universal feelings of wanting to be noticed, to be beautiful, to be strong and to be fabulous, which is why it became a huge # 1 hit in 1990. This was the genius of Madonna, by taking something from the gay underground and bringing it to the mainstream she managed to sneak gay culture and gay people into the living rooms of middle America. Like Into the Groove it's also a celebration of dancing and few songs fill the dance floor up quicker than Vogue and yes once again it was played at my wedding. I also danced to Vogue as a 12 year old at another wedding and broke out all the entire routine! Yes I was that that gay at 12. For me Vogue is the standard against which all other dance songs are measured against. Few pop songs celebrate a specific culture while speaking to everyone else at the same time and that's why Vogue remains Madonna's peak.