Key learnings from watching every Madonna video

Last year I set myself the challenge of watching every Madonna video – all 68 of them. I generally enjoy Madge’s oeuvre, and she is indeed noteworthy not just as a pop singer but also as a video artist. She helped shape the emerging art of the music video.

But yet I was pretty sure I hadn’t seen every one of her music videos, particularly that period in the late ’90s when I’d sort of gone off her for a bit. Details of my Madonna-watching journey can be found over on Tumblr, but here I present my key findings.

Madonna has a reputation as a constant reinventor of her look, but when it comes to fashion, she’s actually a bit more conservative than you’d think. Madonna knows that certain shapes flatter her more than others, and she largely sticks with those.

1990s screen saver styles in "Love Profusion"
1990s screen saver styles in "Love Profusion"

1940s-style dresses and suits pop up a lot. One first appeared in “Live to Tell”, and I can’t help get the feeling that this was the start of Madonna’s campaign to be cast as Eva Peron in “Evita”. In fact, the video to “Take a Bow” was especially styled like that as an unsolicited audition. But even after “Evita”, Madonna stuck with the look, donning a 1940s floral frock in “Love Profusion”, which seemed to attract a swarm of popstar-eating CGI fairies.

Toned arms and boofy hair in "Papa Don't Preach"
Toned arms and boofy hair in "Papa Don't Preach"

The corset top is another fave. When it first appeared in “Papa Don’t Preach”, Madonna had been working out and had ditched the baggier boytoy-era clothes. The corset top was perfect for showing off her toned arms and leaner figure. Sometimes it’s part of a dress, like in “Like a Prayer”, and it fit right in with her pervy Madonna phase. And the biggest advantage – after having a couple of kids and getting older, a corset top is just right for holding everything in, like when she’s prancing about with Justin Timberlake in “4 Seconds”.

A monocle, a mansuit and a crotch-grab in "Express Yourself"
A monocle, a mansuit and a crotch-grab in "Express Yourself"

Then there’s the mansuit. You know Madonna – she’s so confident with her sexuality as a woman that she can dress like a man. Madonna dressed liked a boy in “Open Your Heart” and “Who’s That Girl”, but it wasn’t until the power video of “Express Yourself” where she got in full mansuit mode. But it’s a mansuit that always has a bra underneath it, as if to prove she’s still got the lady skills under that big old suit.

Madonna appears in cartoon form in three music videos. In “Who’s That Girl”, Human Madonna (dressed as a boy) sees a fortune teller who shows her Cartoon Madonna, a likeness of Madonna’s “Who’s That Girl” film character, Nikki Finn. Wait, what? It seems a elaborate way for Madonna-the-popstar to distance herself from Madonna-the-actress.

Gap-toothed cartoon Madge in "Music"
Gap-toothed cartoon Madge in "Music"

“Dear Jessie” was only released as a single in Europe and Australasia, so Madonna didn’t participate in the music video. Instead she’s animated as a twee fairy, flying about, being all delightful and shit.

And animated Madonna appears for the third time in “Music”. Human Madge is out on the town with her girls, when Cartoon Madge appears on a TV. A superhero, she flies around a city, kicking arse, knocking about neon signs of her old song titles, hits the dancefloor, before falling to earth. Why is that part done as a cartoon? Did the video’s CGI budget not stretch that far?

Madonna has done a lot of songs for film soundtracks. She had a small role as a nightclub singer in “Vision Quest”, a romantic drama which also explores the serious issue of manorexia. She contributed two songs to the soundtrack – “Crazy For You” and “Gambler”. Unfortunately “Gambler” is not a cover of the Kenny Rodgers classic.

Madonna makes a poor lifestyle choice in "Into The Groove"
Madonna makes a poor lifestyle choice in "Into The Groove"

Madonna’s feature debut is the ace feminist caper flick “Desperately Seeking Susan”, for which she also contributed the perfect pop of “Into The Groove”. The video of this solely consists of footage from the film, but cleverly edited to thematically match the lyrics.

There’s also “Vogue”, which was on the “Dick Tracy” soundtrack but didn’t actually feature in the film. The music video only vaguely alludes to 1930s style. Nonetheless, it’s one of her strongest, most evocative songs and is great to dance to.

Madonna gives Madonna the bash in "Die Another Day"
Madonna gives Madonna the bash in "Die Another Day"

What, you think achievement hound Madonna would pass up the opportunity to sing the theme tune for a James Bond film? With the legendary John Barry long retired from Bond composing duties, Madonna teamed up with a French progressive-electronica producer and made something that sounds like a battle between a robot and ’80s Madonna. The video is bombastic, with Good Madonna battling Evil Madonna. “Sigmund Freud,” she murmurs, “analyse this.” Better than the actual Bond film? Take that, Lee Tamahori.

And you know what else has to be mentioned? Evita. The only original music video is for “You Must Love Me”, probably because the film performance was sung live with Eva on her deathbed. That video features Madonna singing the song behind a grand piano, trying to not look heavy with child. The other two videos – “Don’t Cry For Me Argentina” and “Another Suitcase in Another Hall” were montages from the film, most likely due to Madonna having just given birth to babby Lourdes.

Well ahead of the furry trend in "Like a Virgin"
Well ahead of the furry trend in "Like a Virgin"

Rewatching all the old Madonna videos reminded me of the period when Madonna was controversial. Moral groups and the Vatican seemed to perpetually condemn her for all the sensual writhing she did in videos, and the power combo of religious icons with lady bits. Not the mention the alarming “Like a Virgin” video, in which Madonna is far ahead of the curve with furry love.

I was at exactly the right (wrong) age when parents were concerned that Madonna smoking in “Desperately Seeking Susan” (and indeed the “Into the Groove” video) would influence young girls. But it didn’t make me want to smoke. It made me want to live in a grungy Manhattan loft with a boyfriend who looked like Aidan Quinn. Neither of these futures happened.

I was surprised to discover the very clear distinction made between Madonna and the characters she plays in the videos. In “Material Girl”, the Marilyn Monroe-esque Madonna is set up as a character played by the down-to-earth Actor Madonna. In “Like a Prayer”, the video ends with the cast taking a bow as the curtain falls on their dramatic performance. Yeah, that time when Madonna kissed the black Jesus? That was just a character she was playing.

If you were to plot the moral tone of Madonna’s videos on a graph, it would look like a sine wave, a gentle flow between moral and immoral and back again.

Madonna is also ahead of the loldogs trend in "Human Nature"
Madonna is also ahead of the loldogs trend in "Human Nature"

This is how to seems to work – Madonna pushes the envelope as far as she can go, but as soon as things start to get too outrageous, she’ll bring out something sweet and lovely. When I say outrageous, it’s not just stuff like the Vatican condemning a particular song, but when album sales suffer from songs being a bit too pervy.

So you’ve got the race-and-religion shocker of “Like a Prayer” and the in-your-faceness of “Express Yourself” followed by the sweet, mermaidy “Cherish” and the maternal “Dear Jessie”. And the sexual fantasies of “Justify My Love” and whips-n-chains seriousness of “Erotica” are followed by the repentant “Bad Girl” (“I’m not happy when I act this way”). But pervy Madonna keeps surfacing. Even the real-life phase of being a nice English mum was soon enough followed by 51-year-old divorced Madonna grinding up against Jesus, her hot 23-year-old model boyfriend in the “Celebration” video, and look – Madonna’s doing some freaky yoga moves in the “Sorry” vid. You can’t keep the old girl down.

Madonna still has it in "Sorry"
Madonna still has it in "Sorry"

My top 10 fave Madonna videos

  • Burning Up (1983) – Crazy postmodern imagery and Madonna’s clearly in charge.
  • Material Girl (1985) – The boytoy look takes a break for Hollywood glam and, why, hello Mr Carradine.
  • Papa Don’t Preach (1986) – The first 16 seconds are perfect, the rest is a swell melodrama.
  • Express Yourself (1989) – Inspired by the groundbreaking “Metropolis”, directed by David Fincher, it’s a stylish masterwork.
  • Justify My Love (1990) – Madonna at her perviest, but keeping it cool by bursting out with laughter at the nutsness of it all.
  • Deeper and Deeper (1992) – A bangin’ house track given an arty video with Madonna playing a rather young woman with a thing for older men.
  • Rain (1993) – Directed by Mark Romanek and starring Marc Newson’s Lockheed Lounge chair, every frame is beautiful.
  • Don’t Tell Me (2000) – Cowgirl Madonna kicks up her heels with some cowboys, subverting the cheapie greenscreen video.
  • Hung Up (2005) – Madonna dances, the kids on the street dance, then she goes to a club and shows the DDR game how to dance.
  • 4 Minutes (2008) – Giant black screen terrorises Madge and Mr JT!

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