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Happy 60th Birthday, Madonna: A Trip Through Her Best Songs

By Kayleigh Donaldson | Celebrity | August 16, 2018 |

By Kayleigh Donaldson | Celebrity | August 16, 2018 |

Madonna Met Gala Getty.jpg

The Queen of Pop, Madonna Louise Ciccone, turns 60 today. Better people than me have written thesis after thesis on her remarkable musical legacy: Her consistent boundary-pushing, both as a musician and performer; her game-changing music videos that transgressed social mores as frequently as they forced the medium to evolve; her chameleonic looks and business savvy; her astounding live shows; and, of course, her terrible movies. Where does one even begin with her work? It’s impossible to cover everything, so I won’t bother. Instead, we shall celebrate her best songs, the biggest landmarks in her career, and a few of the under-appreciated numbers.

Don’t just stand there, let’s get to it.


Her first hit remains one of her top pure pop tunes. It’s utterly infectious, a testament to ’80s dance-pop and with a hook you’ll just never get out of your head. It’s the song that signalled the arrival of a new pop princess, but it didn’t hint much at what lay ahead.

Material Girl

Madonna has always been a cinephile. Her music is littered with classic Hollywood references, as is her impressive videography, but this was really the calling card for that. Material Girl sees her appropriating Marilyn Monroe’s famous Diamonds Are a Girl’s Best Friend performance from Gentlemen Prefer Blondes, right down to the smallest detail. A lot of people wrote off the video and song as skin-deep narcissism - the wannabe icon draped in the image of a true icon - but that ignores the rest of the video, wherein Madonna is acting the part of a material girl as a big shot Hollywood filmmaker has his interest piqued in her show. In terms of her establishing her ability to change her persona at the drop of a hat, it’s mega savvy. And of course, that’s a banging tune.

Like a Prayer

Ah, the song that’s confused many a college acapella group and Christian youth choir. Madonna’s always tested boundaries, but Like a Prayer wasn’t so much a button pusher as an atomic blast. Stylistically, it’s a beautifully composed song, combining pop, rock, and gospel. Madonna’s never sounded more emotional and it’s hard not to be completely roused by the 5 minutes of pure force. But of course, the thing that angered everyone was the music video. The Vatican condemned it! Catholic groups protested! Pepsi dropped her sponsorship deal! Good times. And it’s still one of her best songs.


What does one say about Vogue that hasn’t been parroted by critics for years now? Madonna took inspiration from the ball scene of New York and had the legendary Jose Gutierez Xtravaganza choreograph her homage to both the escapism of the club scene and classic Hollywood. Her spoken word name drops of the era’s most iconic stars created a new cultural context for something many of her fans may not have been aware of at the time. It’s an anthem, pure and simple. And yes, David Fincher’s direction on that video is flawless, as it is on Express Yourself.

Justify My Love

Justify My Love is not a great Madonna song but its importance is major for two reasons: One, it samples Public Enemy, putting Madonna in conversation with hip-hop for the first time, and two, that video. How do you top pissing off the Church? You go full BDSM! Fetish, bisexuality, dominatrix garb, cross-dressing, corsets… It was all too much for MTV but it was simply another step forward for Madonna’s transgressive approach to sex. Why be ashamed of something almost everyone does? Madonna also pioneered releasing music videos on VHS after MTV refused to air this one, which offered her a hefty profit as well as a major stage to talk about artistic censorship. She’d continue down this path with the album Erotica and her book Sex, which is amazing and weird and features Vanilla Ice and Udo Kier. Together at last!

Bedtime Story

Erotica led to people claiming Madonna was wilfully overexposed - often literally - and her follow-up album Bedtime Stories feels like a response to that in many ways. It’s trippier but still musically accomplished, reminding critics and audiences that she could still deliver the goods. Bedtime Story was co-written by Björk and feels more in line with trip-hop than anything else Madonna had ever done at that point. The video, directed by Mark Romanek, also remains one of the most expensive music videos ever made.

Human Nature

More R&B than pop, Madona’s ‘fuck you’ to her critics from the Erotica era is almost a sequel to Express Yourself. Where that song is an empowering proclamation for women everywhere to demand better from their men, Human Nature is the aggressive clap-back to everyone who calls said liberation ‘too much’. Madonna has always positioned herself as the canvas for social commentary. It doesn’t always work but this one proved immensely satisfying.

I’d Be Surprisingly Good For You

Look, Madonna is not an actress. Despite her best efforts and her ability to steamroll over every indication that movie star fame just wasn’t going to happen, she never had the inherent talent. That’s not to say she couldn’t be good in the right role. She’s perfectly cast in Desperately Seeking Susan and she’s delightfully vampy in Dick Tracy. For Evita, she was both all wrong and utterly right. She’s wrong in that her vocal range is nowhere near what the role of Eva Peron requires, but as Patti Lupone famously said, that role was abhorrent for any woman to sing 8 shows a week. However, if you want to tell a story about a highly ambitious social climber with an acute understanding of their own appeal as a celebrity, Madonna is, if nothing else, great meta-casting. Evita is not a great musical or a great movie but Madonna’s actually very good. Her best song was never released as a single, but in I’d Be Surprisingly Good For You, she nails a seduction number.


For me, Ray of Light is the peak of Madonna’s abilities as a musician. It’s as close as she’s gotten to a perfect album. I could honestly put all her songs from that album on here but I’d decided to go with one: Frozen. What is there to say about this witchy and deeply melancholic number, equal parts mystical and epic? It’s the sort of song that makes you want to go after every many who ever broke Madonna’s heart. Seldom has chilliness sounded so entrancing.

Don’t Tell Me

Music was a mixed bag for Madonna but Don’t Tell Me is a stand-out. The Sheryl Crow comparisons are obvious, but the layers and textures to this country-tinged number go deeper than that. The combination of beats and guitar riffs give it an oddly sensual feeling. The strength of the song is all the stronger given its status as a follow-up to the decent but unremarkable Music.

Hung Up

The American Life era was not a great time for Madonna - oh god the rapping, the bad social commentary, the disastrous cover of American Pie - but Confessions on a Dance Floor more than makes up for it. Madonna returns to her musical past and proudly homages disco as well as placing herself in conversation with her forefathers, the legendary ABBA. This is a song with one giddy but certain purpose - to get you dancing in the club, and boy does it do that!?

Living For Love

The past few years haven’t been creative peaks for Madonna. It’s been a wee bit sad to watch someone who always stood at the edge of the Zeitgeist now frantically run behind new trendsetters and try to keep up. I can’t deal with the crap about her needing to ‘grow old gracefully’ because it’s sexist and ageist as all hell. I kind of admire her refusal to stop making the sort of youthful pop bangers that she made her name with, even if I do wish they were just stronger on a basic musical level. Rebel Heart, her most recent album, felt like a step in the right direction. It’s wildly uneven, but when it’s firing on all cylinders, it’s a great dance-pop record. Living For Love is easily the best song she’s released since Sorry.

So happy birthday to you, Madonna! May you celebrate disgracefully.

What’s your favourite Madonna song? Let us know in the comments.

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Kayleigh is a features writer for Pajiba. You can follow her on Twitter or listen to her podcast, The Hollywood Read.

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