Top 10, Listen

Top 10 Madonna Songs

Madonna had her heyday back in the 80s and early 90s, but that doesn't mean she isn't relevant today. In fact, the Queen of Pop has been in the news lately thanks to her recent collab song "Vulgar" with Sam Smith. (And also that nasty bacterial infection she's had to overcome.) She may be in her 60s, but the woman still knows how to keep up with current musical trends and social attitudes.

Madonna's early story as a musician is a classic hero's journey. She boldly dropped out of college and moved to New York City in 1978 – at the humble age of 19 and with only $35 in her pocket – to pursue a career in modern dance. After performing as a drummer, guitarist, and vocalist in the rock bands Breakfast Club and Emmy, she rose to solo stardom with her debut studio album, Madonna (1983). She followed it with a series of successful albums, including all-time bestsellers Like a Virgin (1984), True Blue (1986), and The Immaculate Collection (1990), as well as Grammy Award winners Ray of Light (1998) and Confessions on a Dance Floor (2005).

Madonna's pop music is paradoxical in the sense that it can be extremely radio-friendly while also stirring up controversy. She's always been bold in her style and artistry. And that's why so many other successful musicians – such as Lady Gaga, Britney Spears, Rihanna, Katy Perry, and Beyonce – have been influenced by her. As Rodrigo Fresán has put it,"saying that Madonna is just a pop star is as inappropriate as saying that Coca-Cola is just a soda. Madonna is one of the classic symbols of Made in USA."


Check out our selection of free stations streaming Madonna music at Live365.com.


Now, we're finally listing our Top 10 favorite Madonna songs! Please note: due to the INSANE amount of hits in Madonna's catalogue, we haven't been able to mention all of her tunes that we adore. Regardless, we hope you agree the 10 bops below are some of her best work. Let's get into the groove!

10. "Lucky Star"

Twinkly, romantic, and carefree, "Lucky Star" is an upbeat dance-pop tune that was released as the fourth single from Madonna’s self-titled debut album. It was the young artist's first top 5 hit, charting at #4 on Billboard’s Hot 100. Madonna originally wrote the song for Mark Kamins, the DJ who produced her first single “Everybody,” but she eventually took it for her own.

The simplistic music video, which MTV put on heavy rotation, kickstarted the interest in Madonna’s unique fashion sense that dominated 80s pop culture. Madonna initially didn’t want to release the happy-go-lucky song as a single. However, since she was getting sued and needed money at the time, music executive Jeff Ayeroff was able to convince her that releasing the song as a single would get her the money she needed. Hopefully Madonna counted her lucky stars, because he was right!


9. "Borderline"

This is one of those Madonna songs that's STILL played regularly on radio stations. "Borderline" was Madonna's first Top 10 hit and was released in 1984. Produced by Reggie Lucas, the song depicts the ups and downs of a relationship. On the one hand, Madonna's happy when her lover holds her in his arms. But on the other hand, she sings in the second verse, "something in your eyes is making such a fool of me." He lets her down over and over again, and he keeps pushing her lover "over the borderline."

The popular video that accompanies this song depicts Madonna in her iconic clothing style. (She rocks every denim and leather jacket she puts on.) The pop starlet spends time with her temperamental boyfriend in the hip hop scene on city streets. She also models for a snobby photographer.


8. "Papa Don't Preach"

"Papa Don't Preach" is a lyrically easy-to-follow song that can be interpreted in many different ways depending on the values of the listener. Created by songwriter Brian Elliot after overhearing gossiping teenagers, it tells the story of a young woman that has a close relationship with her father. Despite being his "little girl," she shares her apprehension: she reveals she's been seeing a lover he disapproves of and that she is now pregnant. She then reveals that she's made up her mind, and will be keeping the baby.

Of course, all the different interpretations of the speaker in the song stirred the controversy pot. Many feminists and reproductive rights activists were concerned about the character's decision. Alfred Moran, the executive director of Planned Parenthood at the time, made a statement. Parents were worried their teen girls would want to run off and get pregnant. But Madonna loved the critiques. "There were so many opinions. That’s why I thought it was so great," Madonna told Rolling Stone. "Is she for ‘schma-smortion,’ as they say in Knocked Up? Is she against abortion? It just fit right in with my own personal zeitgeist of standing up to male authorities, whether it’s the pope or the Catholic Church or my father and his conservative, patriarchal ways."


7. "Express Yourself"

Considered Madonna's most influential tune, "Express Yourself" is a feminist anthem and a sonic homage to the ‘70s funk-soul of Sly & The Family Stone and The Staples Singers. It offers an important message to women that they should not be afraid of the outcome of relationships. There's no point staying in one of they're being subdued by their partner.

Madonna explained to The New York Times, "The message of the song is that people should always say what it is they want. The reason relationships don’t work is because they are afraid. That’s been my problem in all my relationships. I’m sure people see me as an outspoken person, and for the most part, if I want something I ask for it. But sometimes you feel that if you ask for too much or ask for the wrong thing from someone you care about that that person won’t like you. And so you censor yourself. I’ve been guilty of that in every meaningful relationship I’ve ever had."

Fun fact: the music video for "Express Yourself" was directed by David Fincher. Y'know, before he put out hit movies like The Social Network, Gone Girl, Mank, and Zodiac.


6. "Holiday"

The cheery song that put Madonna on the map. “Holiday” is Madonna’s third single, being the singer’s first mainstream hit. In the United States, it peaked at #16 on the Billboard Hot 100 – it was Madonna’s first single to enter the chart. The song was also #1 on the Billboard’s Dance Club Songs chart and top 10 in several countries.

According to setlist.fm, "Holiday" is the song Madonna has performed the most live. It makes sense, given it's a simple tune about taking time to relax and cherish the good times. "Holiday" reminds us that we all need to take one day out of life to celebrate!


5. "Like a Virgin"

"Holiday" may have cracked onto the Billboard Hot 100 first, but "Like a Virgin" is considered the breakout hit that forever cemented Madonna as a pop deity. This was the first of Madonna's bangers to top the charts and hit #1 at the end of 1984. Catchy and melodically sweet, this song communicates the healing power of being in a healthy relationship, and how it can feel like your very first time in love. Therefore, when Madonna's with her lover, she feels "like a virgin, touched for the very first time".

Fun fact about this tune: it was originally meant to be sung by a male performer. Its lyrics tackle the relationship woes of writer Billy Steinberg. He explained to the Los Angeles Times: "I was saying...that I may not really be a virgin — I’ve been battered romantically and emotionally like many people — but I’m starting a new relationship and it just feels so good, it’s healing all the wounds and making me feel like I’ve never done this before, because it’s so much deeper and more profound than anything I’ve ever felt."


4. "Into the Groove"

What makes "Into the Groove" different from your average dance club song is the passion with which Madonna sings about dancing. "Into the Groove" is a love song both to a stranger she's just met on the dance floor, as well as an ode to the act of dancing itself. Perhaps this concept is best exemplified in the pre-chorus lyrics: "Only when I'm dancing can I feel this free / At night I lock the doors, where no one else can see / I'm tired of dancing here all by myself / Tonight I want to dance with someone else."

"Into the Groove" was recorded for the film Desperately Seeking Susan – hence why the music production has a dramatic edge to it. It was also featured on the re-issue of Like A Virgin. Not only is "Into the Groove," well, groovy...it's also a reminder that Madonna's first love wasn't singing, but dancing. Her infatuation with the art is utterly infectous.


3. "Material Girl"

A song about consumerism that's actually positive for a change. We think "Material Girl" is probably the most fun Madonna song there is. Between those iconic guitar riffs, the robotic-sounding man voice interludes ("li-ving in a ma-ter-i-al world."), Madonna's high-pitched energy, and that Gentleman Prefer Blondes inspired music video, "Material Girl" is a classic through-and-through. In a way, the Like a Virgin song feels like a microcosm for the hyper-consumerist culture of the 1980s. Case in point: that mall scene from season 3 of Stranger Things.

But don't get it wrong: Madonna isn't bashing true love and humility in "Material Girl." She's not being a cold gold-digger. Rather, she's saying Mr. Right should be loving, affectionate, and provide her with financial security. Materials are a symbol of stability, after all. It's this important message to women – that you should use both your heart AND your head when finding the right person – that makes us love "Material Girl." And we also adore the truth of that line, "experience has made me rich and now they're after me." It reminds us that if we love and work on ourselves, the suitors, as well as the materials, will come naturally!


2. "Like a Prayer"

Only Madonna can craft an earwormy song that intertwines God and sex. Towards the end of the 80s, she wanted to cater more to her adult audience. So in 1989, she released “Like a Prayer,” and it signaled a more artistic and ultra-personal approach to her songwriting. The woman's name is Madonna after all...of course she'd want to craft a banger about religion!

There's some incredibly naughty-but-genius wordplay in this bop ("When you call my name / It's like a little prayer / I'm down on my knees / I want to take you there), and the gospel choir vocals? Chef's kiss. "Like a Prayer" became her seventh chart-topper, and was critically lauded for it's musical complexity.

Of course, we can't talk about "Like a Prayer" without mentioning the controversial music video, which is considered one of the best visuals of the 80s. It follows Madonna after witnessing a homicide, seeing a Black man falsely accused for it, and wandering into a church as she contemplates what to do next. People were up in arms about the burning crosses and Madonna kissing a Black saint, but those were the reasons why MTV gave the video heavy airplay. Despite the Vatican protesting the video and Madonna losing a Pepsi campaign over the controversy, the visual received great reviews from critics and won the Viewer's Choice category at the 1989 MTV VMA's. Coincidentally, the award show was sponsored by Pepsi that year.


1. "Vogue"

A debatable choice, given a plethora of other Top 10 Madonna Songs lists have placed "Like a Prayer" at #1. Yes, that song is considered her most commercially successful work. But we beg this question: if it hadn't been for the buzzworthy music video, would the legacy of "Like a Prayer" have been as great?

This list is judging Madonna's music, not necessarily her imagery. To us, "Vogue" is to Madonna's discography what "Toxic" is for Britney Spears: not the first song you think of when you think of the pop princess, but lyrically meaty, vocally impressive, and sonically powerful enough that it still sounds cutting edge several years later. It can also be seen as a precursor to Lady Gaga's hit "Born This Way." as "Vogue" is similarly about embracing your unique identity and letting out your inner superstar.

There's so much more to unpack with "Vogue" than there is with "Like a Prayer." For example: the fact that this brought the New York underground ballroom scene – as well as the heavily LGBTQ+ inspired dance style of voguing – into the limelight. Then there's that iconic old Hollywood rap in the bridge ("Greta Garbo, and Monroe / Dietrich and DiMaggio..."), the chic black-and-white music video with shots that could all be magazine covers, and that genius Marie Antoinette-inspired VMAs performance with the fan toss trick that – rumor has it – miraculously went right despite several failed attempts in rehearsals.

"Vogue" was supposed to be associated with Madonna's I’m Breathless soundtrack meant to accompany the film Dick Tracy (1990). Instead, it rang in the glitz and glamour of the early 90s, particularly in the metropolitan club scene. Whenever this flashy song plays, we can't help but strike a pose, move to the music, and go with the flow.


Check out our selection of free stations streaming Madonna music at Live365.com.

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Article Image: Image of Madonna's "True Blue" album cover on vinyl. (Ralf Liebhold via Shutterstock.)

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About Kathryn Milewski

  • New Jersey