Say which flavour you like and I'll have it for you: Suedey's Madonna top 50

The singles from COAD were perfect. Sorry was the most commercial thing on there after Hung Up. Jump was obviously a bop, but it is very gay. Get Together is obviously the best song, but it was too much of a sultry gem to smash.
No lies detected.
 
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49. Like A Virgin (Like A Virgin, 1984)
UK chart position: 3
Key live version: Blond Ambition Tour (1990)
Key remix: Extended Dance Mix (1984)



I can almost hear the collective groans and see the eye rolls but hear me out please. ‘Like A Virgin’ = Madonna. It is as simple as that. It is a chameleon of a song in live format – just as she is. It is a delicious juxtaposition of contrasts – just as she is. And it is, quite simply, sordid – just as she is. Bubble-gum pop was never the same again after this song. I still marvel at the sheer audacity of her at that early stage in her career and in the ‘80s, blatantly singing about not being a virgin. A lot of feminists were up in arms at the time with headlines like Madonna setting back the women’s liberation movement by 50 years of something thanks to songs like this but they had it all wrong. ‘Like A Virgin’ is probably the most effortlessly feminist statement of her entire career (ironically penned by two men). In studio form it is quite simple, and the bassline is very reminiscent of ‘Billie Jean’ (which she acknowledged by interpolating into the Virgin Tour performances in 1985).

'It hurts. It hurts her. It shouldn't hurt. You know, her pussy should be Bubble-Yum by now. But when this cat fucks her, it hurts. It hurts like it did the first time.
You see the pain is reminding a fuck machine what is once like to be a virgin. Hence, "Like a Virgin."' (from Reservoir Dogs)

‘Like A Virgin’ really took on a life of its own with the 1990 Blond Ambition Tour performance where she simulated masturbation with two eunuchs in cone bras. It was brazen, filthy and absolutely genius. Since then, it has had many other incarnations including a cabaret-style reinvention a la Marlene Dietrich (Girlie Show Tour) and the morbid, underrated waltz of a performance in the 2012 MDNA Tour which she sang flawlessly in a far more comfortable lower register. Yes, it is overplayed; yes, it is every basic queen’s go-to karaoke song – but that does not take away its sheen. Not for me at least.
 
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As one of the few artists with multiple signature tunes I wonder what is the most signatory of the signatories?
 
My favourite LAV moment was the COAD tour - it was such a fun interlude between all the sparkling but moody electro in the opening medley. I’ve never been a fan of the song but I’ve had a new respect for its unapologetic joyfulness ever since then.

not in my top 50 though.
 
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48. Hollywood (American Life, 2003)

UK chart position: 2
Key live version: MTV VMA’s (2003)
Key remix: Stuart Price’s Thin White Duke remix (2003)




I suspect this may be another controversial choice but, anyway, my countdown – my rules. ‘Hollywood’ was originally actually conceived as part of the sessions for Music but apparently she was not happy with it then. Of course we all are familiar with the iconic Britney/Christina moment but I would bet that the majority of people would remember the kiss first, ‘Like A Virgin’ second and Missy Elliot third. ‘Hollywood’ itself is all but forgotten.

'How could it hurt you when it looks so good?'
I have always loved this song – it is not a Madonna classic and even though it debuted at No. 2 in the UK this was back in the day when single sales were in the toilet and it swiftly left the top 10 anyway. I love the guitar riff and just how palpably frustrated she sounds. In a way, it represented 2003 for me – it wasn’t a great year for Madonna, and it wasn’t a great year for me on a personal level either. So I really connected with it. The multi-tracks recently ‘became available’ online, and listening to them I really appreciated the layered production. The video I have mixed feelings about: another one of her famous ‘homages’, it was supposed to honour French photographer Guy Bourdin – his family were having none of it though, and they ended up suing her and Jean-Baptiste Mondino. She hasn’t worked with him since (probably due to this fiasco) and I find that a bit of a shame. My favourite scene is actually the fully-clothed hitch-hiking finale which goes full circle back to SEX.

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Hollywood too low. It’s one of those songs that still sounds as good today. I love how ”simple” it is, yet how layered the music is. The silly lyrics work well here with her semi-phoned in vocals (as opposed to the rest of the album). I love the theme of the song and thank God for that ”homage” because I think this was her last great video.

This bird has flown.
 
Hollywood is one of those songs that sounds nice in the background (more so as time goes by), but watching the video back, I remember how irrelevant she felt to the pop landscape when it came out. It's so strange, because only a few years earlier, she had been such a vital force.
 
Like a Virgin is such an exquisite pop song. The definitive version for me is the Confessions Tour version, which really elevates it from bouncy bubblegum bop to massive electro banger - it must be in my top 5 most played Madonna. The much deeper vocal she's serving also lends it a nice element of maturity that just felt right 20 years after the original.
 
Hollywood I think is fantastic, but I massively overplayed in the early years of my standom and now it's one I'd rarely go back to. but when I do, I really enjoy it - the airiness of the production, the breezy guitar riffs, the dorky but somehow successful pitch-shifted middle 8. the fusion of guitar and heavy electronic beats as it progresses makes it feel sonically adjacent a lot of the Music album.

I remember being stunned that it wasn't huge at the time. I was just starting to stan, I think American Life's singles were my intro point to Madonna (other than hearing Beautiful Stranger and Music a lot on the radio). commercially grim days for the good sis though.
 
Of course, I maintain that American Life (song) should have been a 16-week #1, and that the original video should have been released as intended (her career died on its arse in the US afterwards anyway, and it would have been vindicated as the years passed).
 
There’s something likeable about American Life even to this today. It has a subversive, almost punk quality to it. It’s not edgy or anything, it’s just unapologetic and the music fits the message and the tone. It shouldn’t click but it does. The fact that it can still hold up 20 years later given how divisive it was says a lot.

Hollywood however is a tuneless mess. I get that the chorus is MEANT to be sung flat but maybe it wasn’t the best idea to sing it live on a big stage in front of her peers when she’s generally rather underrated for having a good live voice. She didn’t do herself any favours. It sounded like she was off key if you weren’t familiar with the song.
 
That all being said, Nobody Knows Me is the only track I still go back to from that album. I really liked Love Profusion and Nothing Fails at the time, but they’ve very much stayed in 2003 for me.
 
I was never a big fan of Nobody Knows Me until THAT performance on the Reinvention Tour. It has so much more life than than the album version somehow.
 
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47. Promise To Try (Like A Prayer, 1989)

And so to our first entry from Like A Prayer – not to give too much away, but it certainly will not be the last song from that album. ‘Promise to Try’ is a simple, heartfelt tribute to her mother. When I was younger I didn’t quite understand that the song is actually written from the perspective of her father singing to her as a child. It is a raw, tender vocal like much of the rest of the album, which I suspect was recorded in a single take. Musically, it is a classic Pat Leonard composition written on the piano with accompanying strings. Lyrically, it is one of her most effortlessly touching efforts:


Don’t let me memory play games with your mind
She’s a faded smile, frozen in time
I’m still hanging on
But I’m doing it wrong

‘Promise To Try’ has never been performed live, but it was prominently featured in Truth or Dare/In Bed with Madonnachronicling the Blond Ambition Tour 1990 when she visits her mother’s grave. A highly divisive scene to this day which is either the height of tastelessness or a tender intimate moment (depending on which way you’re inclined).




I'm not sure whether we will ever see ‘Promise To Try’ live – the closest she may have come to considering dusting it off may have been the Tears Of A Clown shows in 2015-2016, but it appears to be all but forgotten unfortunately.
 
I hardly ever listen to it, but it is extremely lovely. And yes, I would love to see a latter-day stripped-down acoustic version live.
 
It is indeed a lovely song, but I don't put it on much either. It's quite understated and reminds me of early Tori, except that Tori probably would have put in a rousing middle eight, while M is keeping it simple and bare, which is probably not something one would usually say about her songs.
 
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46. Joan of Arc (Rebel Heart, 2015)
Key live performance: The Ellen Show (2015)


Madonna’s muses have almost always consistently been strong female figures: from Marilyn Monroe and Marlene Dietrich in the ‘80s to Frida Kahlo in the ‘90s and, increasingly, Joan of Arc in the ‘10s and beyond. In fact, the first hint was actually the Rima Akra dress she wore in the 2012 Golden Globe Awards, with its chainmail motif that, she said, was ‘very Joan of Arc’. Fast forward a couple of years later, and we have an entire song dedicated Joan (and it wasn’t to stop here – Madame X’s ‘Dark Ballet’ is another tribute).

This is my favourite song from the underrated Rebel Heart album. I only just prefer the studio version to the leaked demo version, though I believe that the latter, with its military march rhythm and slightly different lyrics, is more favoured in the fanbase. In true Trolldonna fashion, although the entire Rebel Heart Tour promotional photoshoot was based on Joan of Arc, the song would not feature on the tour setlist and the only proper live performance we have was the televised appearance on the Ellen Show.




Although vocally imperfect (she had a cold at the time), the performance is genuinely emotional and she is almost in tears towards the end. The song may not be an iconic or a life-affirming moment in her career, but I am a sucker for singer-songwriter confessional-type songs and to me that ticks the box perfectly.
 
Joan of Arc is probably my favorite from Rebel Heart alongside Inside Out and Ghosttown. Nothing earth shattering and probably wouldn't feature in my all time top 50, but has that lovely warmth she can exude even in recent years.
 
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45. Angel (Like A Virgin, 1984)

UK chart position: No. 5
Key remix: Extended Mix
Key live version: The Virgin Tour (1985)

1985 was perhaps the peak of MadonnaMania. She was, in fact, coming close to saturating the market – which may be why ‘Angel’ was released with relatively little fanfare and no music video. In the USA, it was a double A-side with ‘Into The Groove’ (which was never officially released there) peaking in the top 5 as it did in the UK.

This is such a euphoric, somewhat saccharine song typical of the Madonna/Steve Bray songwriting partnership at the time. It is very difficult for me to listen to this song without smiling. It is just so effortlessly happy. I really enjoy the vocal performance where she switches from her lower to upper register. It was only performed at The Virgin Tour in 1985 and was excluded from the home video release. The audio is available on YouTube (from 21:27 onwards). The verses are a bit wobbly but by the time she hits the chorus she sounds better.



I’d always had a somewhat troubled relationship with the Like A Virgin album, but in recent years I’ve re-evaluated it and I think it has aged really well. It was such a concerted effort at her entering the ‘big time’ and for the most part, thanks to songs like ‘Angel’, it works really well. It is also quite popular on streaming in her back catalogue in comparison to other, more critically lauded, albums.
 
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44. Rescue Me (The Immaculate Collection, 1990)
UK chart position: No. 3
Key remix: Titanic Vocal (1991)
It is easy to dismiss ‘Rescue Me’ as an inferior cousin to ‘Vogue’ that borrows heavily from Deee-Lite – and some of the criticism is probably justified, but there is no way I’d have a Madonna top 50 without ‘Rescue Me’ in it. The combination of her characteristic spoken word verses with the guttural, throaty chorus emblematic of the laryngitis-frenzy Blond Ambition Tour vocal cord damage is for the ages.

It was never really meant to be a single but radio picked it up and so remixes were commissioned (which are now finally available on streaming!) and the single was released. The lack of a music video is a shame (I won’t talk about the Who’s That Girl Tour medley video). It was used in a Japanese advert where she looked flawless and I’d like to think that could have been a proper video. But anyway it is what it is. In lieu of a video I shall post this fantastically dated MTV clubhouse clip instead.


 
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43. Dear Jessie (Like a Prayer, 1989)
UK chart position: No. 5
Madonna and twee? Not a good combination (hello English Roses 2003 era). Madonna and Christmas? Not a very successful combination in general – at least in the UK (‘Take A Bow’, ‘Love Profusion’ etc.). However, ‘Dear Jessie’ is the known exception to both of these rules. Yes, it is twee but it is also absolutely wonderfully whimsical. A string-laden ode to Patrick Leonard’s daughter (Jessie) sung by (at the time) a childless Madonna. Interestingly, the demo version had a faster pace with drums (see the leaked clip below) with a similar time signature to ‘Till Death Do Us Part’. It would be nice to hear the full demo version one day but to me the slower pace works much better, and the way it segues into the ominous ‘Oh Father’ opening on the album is genius.




Like A Prayer was a huge commercial risk for her but an artistic triumph as an album, and she finally was taken seriously by the misogynistic music press at the time. But with that, her commercial fortunes tumbled a bit. ‘Oh Father’ missed the top 10 in the USA – as a result it was not released in the UK and we got ‘Dear Jessie’ in time for Christmas instead. It’s never been featured on a compilation since and she has never performed it live, but it is one of her most well remembered and loved songs in the UK in my opinion – from random friends and work colleagues mentioning it to me (cwej-tastic evidence based remix) to the fact that I hear it often on UK radio. Anyway, it’s just lovely and that’s that.
 
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