This article originally ran in 2014 and has been updated in honor of Madonna’s birthday on August 16th.
Here’s a funny picture: In July 1983, metalheads and popsters all stormed into their closest Sam Goody, where they likely collided head first in the aisle at M whilst clamoring for Kill ‘Em All or Madonna. Parents scoffed at the time, but either party held the debut album to the future leader of their respective genres. Wild, huh? It’s almost like something out of a Far Side comic; the two most opposite musical forces, both then and today, essentially born as twins. Cowabunga.
Of course, as history goes, Madonna’s self-titled debut didn’t exactly blow out the mall doors upon arrival. The album entered the Billboard 200 at No. 123, and it wasn’t until over a year later that it peaked… at No. 8. It took her third single, “Holiday,” to finally turn heads, which was then followed by “Lucky Star” and “Borderline.” Although her followup, 1984’s Like a Virgin, really introduced the world to the Madonna we champion and pay $300 to see today, the trail of glitter did start here.
So, in light of its 30th anniversary — shh, Madge can’t know, she’ll just get upset — we carved out our top 20 favorite songs. Don’t scoff, we gladly took it upon ourselves to listen to hours and hours of catchy, incandescent pop music. It was a fun process that’s even more addicting than it sounds. (Seriously, I’ve listened to “Borderline” far too many times for one’s own health.) Yet because she’s the Queen of Pop and reigns over a pyramid of hits, we’re sure there will be some omissions.
On the plus side, there’s no room for disappointment — just dancing. Enjoy, and scroll to the end for a playlist of all 20 tracks.
— Michael Roffman
20. “True Blue”
True Blue (1986)
It’s hard to picture Sean Penn when you listen to the cutesy love song “True Blue,” but as Madonna’s then-husband he was the lucky receiver of her heart at that time. Originally written for Penn, the retro feeling song incorporates doo wop in its chord progressions alongside Madonna’s trademark synth chords. What was more unexpected was how the song found itself being covered by the punk rock band Digger. Let’s just hope in this case they were dreaming of Madonna instead of Penn. — Allison Franks
19. “This Used to Be My Playground”
Something to Remember (1995)
Penny Marshall not only brought us a historic film starring Madonna, but also a chart-topping single from A League of Their Own. While it’s beautiful and serene retrospective demeanor stands up on its own, it’s hard not to associate it with the film; being the film’s theme song and all. Plus, it honestly captured the heartfelt emotions of each and every one of those ball players. Just remember, there’s no crying in baseball… the dance floor, however. — A.F.
18. “Open Your Heart”
True Blue (1986)
Madonna’s clever play on cabaret and female empowerment shines through in the coy pop melody “Open Your Heart.” Originally dubbed as a “simple love song,” “Open Your Heart” quickly rocketed into a feminist stomping ground for complaint no thanks to its video. Featuring a young boy seeking out a strip club, only to run away with one of its stars (Madonna) wasn’t necessarily what people wanted to see, but behind the curtain it stood for so much more. It even spawned a wacky industrial polka cover by Atom & His Package in 2001 further proving this song is more than meets the eyes. — A.F.
17. “Take A Bow”
Bedtime Stories (1994)
It’s rare for a song to be both overwhelmingly sexual and heartbreaking at the same time, but “Take A Bow” hits the nail on the head. Perhaps we can blame its iconic music video for its blatant sexual nature; featuring a half-naked Madonna gyrating on her bed. Regardless, it’s not surprising that this song became her longest running single in the US, but more astonishingly her last number one single in the ’90s. I suppose “all the world is a stage and everyone has their part.” — A.F.
Bedtime Stories (1994)
Madonna has received both positive and negative connotations for her sex icon status. However, in 1992, after the release of her controversial book, Sex, and her equally controversial album, Erotica, pretty much everyone was screaming in her ears, “You’ve gone too far, girl!” So, in an attempt to tone things down and show her fans/critics her softer and even sweeter side, “Secret” was released as the lead single for Bedtime Stories. However, did she achieve this? Well her coy and innocent smile in the music video speaks for itself, but the song can’t hide its true meaning for long. After all, there’s nothing sexier than a secret. — A.F.
“Music makes the people come together.” Yeah, pop can be pretty literal, but it doesn’t get more basic than that. Yet here we are talking about what’s arguably one of her biggest hits to date. Produced by French DJ Mirwais Ahmadzaï, who she thought was “the shit,” the track is nothing more than a comeback anthem, something to turn heads, and given the critical and commercial success of Ray of Light, she really needed something epic to slam down.
So, on August 21st, 2000, “Music” punched hard: on the charts, on the radio, all over MTV and VH1, and, most importantly, every club across the world. It’s almost meta come to think of it; the song did make people come together. Hey, Mr. DJ… — M.R.
14. “Deeper and Deeper”
Erotica‘s eccentric second single was an aural sigh of relief when held up to the exaggerated sexual album as a whole, regardless of its perverted lyrical metaphor (depending how you read into it). The fusion of flamenco guitars, chummy disco, and castanet percussion helped orchestrate a tale of a young man accepting his own homosexuality — a bold move given it was still a taboo subject in 1992.
What’s even bolder was its nods to The Sound of Music and past single “Vogue,” not to mention its accompanying nutbar video which featured cameo appearances by the likes of Udo Kier, Sofia Coppola, and Debi Mazar. Udo Kier! — A.F.
Who knew a song about male chauvinism would be so fun to dance to? “Borderline” is that very song which helped push Madonna into the limelight on her debut release. For its time, the sentimental track proved itself as ahead of the curb blowing audiences away with her sober lyrics and complex synth harmonies. And with the help of its video, Madonna quickly became a role model for young girls. What teenage girl doesn’t aspire to be that care free and strong woman who’ll wreak havoc on your walls? — A.F.
Ray of Light (1998)
The tribal mid-tempo ballad off Ray of Light remains one of Madonna’s most introspective hits. It’s the Material Girl doing Portishead and it’s brilliant. From the desolate Chris Cunningham-directed video to William Orbit’s silky production, the single should reek of late ’90s sensationalist pop, but it doesn’t.
It’s an emotional piece that resonates with each listen; the elegant strings and digital percussion marry Madonna’s tragic pitch and let it soar. Lyrically, its mundanity comes across as a threat, a dark and sordid tale, making it one of her bleakest moments. As she told The New York Times: “Retaliation, revenge, hate, regret, that’s what I deal with in ‘Frozen.'” — M.R.
11. “Lucky Star”
Nursery rhymes were brought to a new level of sexual energy with Madonna’s “Lucky Star” back in 1983. Juxtaposing the male body with the stars up above was just the first trick up her sleeve as she chimed, “Come on shine your heavenly body tonight ‘cause I know you’re gonna make everything all right.” Then, she shyly remarks, “You may be my lucky star, but I’m the luckiest by far,” only sparking the innocent romance further. Who can resist that? Who? — A.F.
10. “Hung Up”
Confessions on a Dancefloor (2005)
Okay, so most of the credit goes to ABBA for that riff, that’s agreeable. Still, “Hung Up” is a meticulously designed pop song whose sole purpose is to cling to the listener and get them to dance. There’s no subtext, nor any revelatory beat, but it’s something to marvel at from a production standpoint. The galloping bassline, the battle cry of a sample, and Madonna’s lyrical hooks all make this a blissful exercise in post-disco pop. “Time goes by, so slowly,” she cries. “Every little thing,” she yelps. “I’m hung up on you,” she coos. “I want to listen to this again,” said everyone. — M.R.
09. “La Isla Bonita”
True Blue (1986)
Thanks to Madonna, San Pedro has always seemed like an exotic vacation spot. Too bad it’s only a myth, right? Known best as her first song to carry Spanish influence, featuring Cuban drums, flamenco style guitar and, of course, maracas, “La Isla Bonita” has been referred to as one of her most influential and timeless songs. It’s a little slice of escapism for adventure seekers and home dwellers alike — and probably the only worthy track you’ll hear on Lite FM at your dentist’s office. — A.F.
I’m Breathless (1990)
Since “Vogue” exploded all over the radio in 1990, it’s become the quintessential gay club song. Drenched in glamour and glitz, the I’m Breathless single brings out the inner model in all of us, urging listeners to be nothing more than fabulous. Thanks to another David Fincher-directed video, the track spawned its own dance style, “vogueing,” for stylized house dancers seeking to strike a pose with angular and rigid body movements.
Looking back, the real irony of the track is that at its core, it’s a modern disco track, a genre that was so not in vogue at the time. Then again, the fact that this incredibly ’90s-sounding track eschews any sort of irony when it’s rolled out today speaks volumes to its timeless nature. — A.F.
07. “Human Nature”
Bedtime Stories (1994)
Looking back at 1995, most people probably remember Michael & Janet Jackson’s bondage style space adventure, “Scream,” more so than Madonna’s wacky “Human Nature” video which was actually released first. However, “Human Nature” marked more of a drastic shift for Madonna musically than most people realize. Bringing Madonna more towards R&B, the song rings as a big fuck you and even carries a CrazySexyCool vibe to it with its nonchalant lyrics: “Did I say something true? Oops I didn’t know I couldn’t talk about sex (must have been crazy).” Don’t we all know Madonna’s not afraid of breaking the rules? — A.F.
06. “Into the Groove”
Desperately Seeking Susan (1985)
Every teenage girl wanted to be just like the strange and elusive Susan in the ’80s. And thanks to the film Desperately Seeking Susan, they could imitate all her crazy antics on the dance floor with the irresistible drum machine sensation “Into the Groove.” The song’s all about luring boys with a reckless attitude by saying “We might be lovers if the rhythm’s right” and teaching girls to just let go, feel the music, and maybe throw one’s guard down. Sometimes we look too far into things, but “Into the Groove” just urges the listener to dance and have fun with it. It’s “Music” before we complicated things. — A.F.
05. “Material Girl”
Like A Virgin (1984)
Diamonds are a girls’ best friend, don’t ya know? In 1984, “Material Girl” was at the heart of every valley girl’s fantasy, conjuring up thoughts of materialism in lieu of real relationships. Let’s face it, it fit the decade perfectly and has since been covered by a slew of pop stars as obvious as Britney Spears and as uncanny as Elton John. The simplistic, catchy synth arrangements and robotic echos have charmed our radios for almost 30 years now and we still can’t get enough.
Oddly enough, though, Madonna has remarked on several occasions that she regrets the song’s release as it became a pseudonym for her in mainstream media. That may be true, but that hasn’t stopped it from becoming an All-American anthem. — A.F.
04. “Express Yourself”
Like A Virgin (1984)
To this day, “Express Yourself” holds strong as a female empowerment pop funk song urging ladies to never go for second best (and Lady Gaga to redefine these themes for modern audiences). At the time, it was revolutionary, but as the gender-bending video displays, the same ideology should be applied to men as well.
“Express Yourself” is uplifting regardless of your sexual orientation, paying tribute to soul masters Sly & the Family Stone, all the while as an upbeat dance-pop song. Wild, isn’t it? As of 2022, its David Fincher-directed video remains the third most-expensive music video to date. — A.F.
03. “Like A Prayer”
Like A Prayer (1989)
Inspired by her Catholic upbringing, “Like a Prayer” capitalizes on elements of gospel music to portray a rather strange and scandalous interpretation of religion, sex, and life in general. However, the song’s uplifting backup choir speaks divinely to one’s heart, making everyone question the idea of sin altogether.
As she chimes, “Oh god, I think I’m falling,” her bra strap slowly falls, to which she cries: “Out of the sky I close my eyes/ Heaven help me.” This only leaves a sea of boys (and plenty of gals) to think, “God help us all.” If the King of Pop had his life affirming moment with “Man in the Mirror,” consider this the Queen’s. — A.F.
02. “Ray of Light”
Ray of Light (1998)
Fit for the closing credits of a Danny Boyle picture, no thanks to producer William Orbit, “Ray of Light” has and always will be one of the best electronic pop tracks of its kind. Welding together traces of techno, disco, rock ‘n’ roll, and enough sound effects to blow up a Kenner toy gun, the 1998 single is one of the most complex tracks in Madonna’s storied repertoire.
Unlike, say, fellow album track, “Frozen,” there’s a depth to her lyricism that’s not only alluring, but downright creative. “Zephyr in the sky at night I wonder/ Do my tears of mourning sink beneath the sun,” she repeats throughout, sounding less like the Material Girl of yesteryear and more like a balmy Billy Corgan. Influential for the millennials, a favorite amongst the veterans, and a regular staple 15 years later — it doesn’t get better than that for a single off one’s seventh album. — M.R.
01. “Like A Virgin”
Like A Virgin (1984)
Adolescence is a strange time for everyone, but Madonna’s iconic “Like a Virgin” still turns the subject of virginity on its head. Combining sexual experience with a desire to regain childhood innocence, the Queen’s first No. 1 single will always remain a cultural artifact of the 1980s. (As will the infamous Weird Al cover “Like A Surgeon,” but that’s another story.) After all, this is what helped transition Madonna from the radical cover girl into the rebellious sexual enigma that’s changed the genre forever.
And while “Like a Virgin” first threatened her career as a one-hit wonder, Madonna’s 30 year-long resume of visionary and scandalous pop, instead, makes it the prologue. So, when your kid shrieks at the new Lady Gaga or Katy Perry record, put this one on for a spin with the advice to “start here.” — A.F.
Madonna’s Top 20 Songs Playlist: