Top Ten Madonna Songs

Into the Groove. Could it top the charts?

We met. Did I tell you that?

Did I ever tell you I met Madonna once? It was in Cipriani’s in Park Lane. Prince Andrew (Booo!), Sarah Ferguson and their kids were also dining there that night. As was I. Anyway, she and I met, but briefly. You can read my account about meeting Madonna in this very blog. For her side of the story, you’d need to ask her. Recollections may possibly vary but - for myself - I’ve said all I’m going to say about the incident. Unless asked. Or pissed.

Love her or loathe her, she’s certainly had a long career. From her bouncy lightweight pop in the early 80’s to her move toward more convention-defying music of the early 90’s through to producer-led techno of the mid 90’s onwards thru to soundtracks, she’s produced a decent catalogue of songs.

Now, dear reader, I know I’m famous for my reviews of classic rock (really Tim?) but a decent pop song will always get me going. Songs date you, they place you in a certain time and certain place. I span all Madonna’s career. As she was breaking through I was just starting to go to clubs (discos in those days, kids). We’ve kind of had a parallel existence; her dominating the pop world and me, well, yeah.

The Top Ten

So, I thought I’d do my top ten Madonna tracks in homage to her, our brief time together, some memories of a bygone era and because her stuff always creeps onto my playlists when I’m off for a long drive. Don’t expect a deep dive here; they’re not really that kind of songs. We’re talking a feeling, a hook, a look, a place and a time. We only met once, but, through her music, we coalesced multiple times.

Scanning through the candidates for the top ten you’ll notice there’s eleven on the list. Why? Well, who said I can’t subvert the listette convention. No rules, man. But I genuinely found it hard to slim the list down to ten, so I chickened out on which songs to leave out. So, eleven it is. The other unsuccessful songs from my long list appear below. You think this stuff is easy?

In reverse order:


10 - Music

Hey Mr DJ, put a record on!” A firm number 10 on the list. A solid dance floor hit. Electronically treated with an earworm high pitched guitar punctuating each phrase. It could be dismissed as Madonna enslaved to production but she’s too good to be pigeon holed for that. It’s got a chorus, it’s got a groove, it’s talks about dancing. Must be Madonna. Video’s not bad either. Aiyee!


9 - Vogue

“Strike the pose” Madonna self styling herself as a serious artist, an artist of the dance floor. Am I alone in picking up a little bit of ‘Going to a Go-Go’? No? Just me then. Love the stepped housey piano on the chorus - whatever happened to that keyboard sound? And then Madonna starts riffing about famous movie stars, they’re all a bit obvious - Dean, Monroe, Harlow, Fred and Ginger - but I’m sure they appreciated the call out. It fits with the song though “vogue, vogue, vogue.”


8 - Sorry

The latest track on the list. To be honest, I missed this when it came out being otherwise distracted by, well, life so I came across it relatively late. Je suis désolé. I was blown away that Madge had pulled out a classic at this late stage in her career. It’s driving, well produced and stands up against her earlier stuff. If she mimed to this at a concert I’d happily do that Tim sway thing along with the earlier classics.


7 - Deeper and Deeper

I bought this single. A cassette single, if I remember. (Ask your parents if you don’t know what this is.) A decent dance groove, one of those tracks where Madge babbles about music setting you free. I’m down with that. Frankly, I’m amazed it’s not higher on the list as I probably play this more often than some higher on the list. My ways are inscrutable. Depends when I’m writing this and what I’m drinking. Deep. And deeper, Tim.


6 - Ray of Light

A comeback of sorts. We were all into Britpop, Oasis and lad bands in the mid 90’s. And then Madonna puts out her 1998 album of the same name which was a massive return to form. The lead single, Frozen, was a turgid misstep but Ray of Light is a shining pop tune for the ages. “And I feel!” she sings as she ramps up the temperature propelling this track into a floor filling classic. She means it, man. I still hit the clubs back in those days and I know I spilt lager on the dance floor to this one.


5- Drowned World / Substitute for Love

Same album. A deep cut. A couple of tunes melded together, stitched together by a beautiful synth guitar part in the middle. Like grunge rock - this is the quiet bit, this is the loud bit. With Madonna, it starts slow and then gets all noisy as the track progresses. This isn’t lightweight pop anymore. This is the older Madonna holding the mic and telling her truth (with a shit load of production helping her). “I now I find, I’ve changed my mind” she sings. I certainly did.


4 - Holiday

Who wouldn’t like this? Bouncy early 80’s lightweight pop. We all like holidays. We all like Madonna’s track singing about holidays. Reminds me of Rochdale which is not a non sequitur. The discos pounded to this when it came out and I started going out! Peak early Madonna. I think - and I may be wrong - that this is the first Madonna song I heard. Certainly the first one I heard in a club. Thing is, when you listen on earphones or on a phone (or earphones attached to a phone) it can sound a bit tame. But at a club, bass turned up, floors bouncing to the music and the dancing, tracks like ‘Holiday’ rocked. Join in - ‘Holiday!’


3 - Skin

“Do I know you from somewhere?” That line always gets me. It’s like she’s singing to me, remembering our one in-person meeting. Another from the Ray of Light album. Techno treated, producer playing the boards but underneath it, a great - slightly melancholic dance track. As you may have realised, Ray of Light, is the only Madonna album I’ve actually bought. The only album I’ll actually play all the way through whilst cooking. There is no higher honour for an artist. Fuck Grammys. If it passes the Tim in the kitchen test, then you’ve made it. When we met, we didn’t discuss this. I might have said “I’m not like this all the time!”


2 - Like A Virgin

This one came out of the blocks and propelled young Madonna away from getting her kit off for ‘arty’ nude photo shoots and into pop royalty. This was the one. Slightly naughty, an effortless pop classic. Obviously Quentin Tarantino’s deconstruction of the lyrics in Reservoir Dogs has added a slightly more layered interpretation but it was always meant to be provocative. Young - and older Madonna - always wanted to create headlines by controversy. Here she succeeds but in doing so rides a great song. Synth bass and lightweight vocals date this slightly but the verve, the melody and the lyrics keep this a seminal Madonna track.


1 - Into The Groove

My go to Madonna track. You have to know the words to the spoken word intro (You can dance. For inspiration. Come on! I’m waiting.). Peak 80’s synth groove. The best Madonna dance track. She likes to dance. She feels free there. Feels a bit jiggy when she dances. Maybe I should have met her in a club instead of a restaurant? Mmm, you’re overplaying your one connection Tim - you’re not bullshitting on a date now. I know. I know. This track reminds me of flecked suits, yellow shirts, sharp haircuts and hair gel. Girls with big hair, discos that burnt down for the insurance money. And Madonna playing loud, bass bouncing off the wooden dance floor, light shows periodically spotlighting your crap dancing as you ‘get into the groove’. Top tune. Top vibe. Number 1. Watch it here.

Bonus Track: Dear Jessie

I debated booting this one off the list and so I did. But. But it’s Beatle-esque production, and my love of it when it came out, demands I keep it at my slightly illegal number 11. Madonna would appreciate my transgression. However, it earned its place with a younger Tim and so - as the solipsism is strong with this one - I kept faith with my younger self. Shout out - love you man. So Dear Jessie is here. Still very Beatles-esque. Its charm wears out quickly though.


Do You Agree?

So that’s my list. I had to whittle it down which wasn’t easy. Borderline. Material Girl. True Blue. Hung Up. They all fell by the wayside as I ruthlessly edited it down to 10 (or 11, yeah, yeah). It was hard. Not as hard as, say, The Beatles, but I’ve spent two years on this blog post so I’ve put the hours in. She’s a major artist and deserved it.

Do you agree? I’m not sure I do myself. Comment below. I usually respond to comments unless they’re weird and have a whiff of your Mum’s basement about them. And so I’ll end by insulting my readers.

Read on

Obviously you HAVE to read my meeting with Madonna. I may have mentioned it a couple of times already in this article.

Maybe my top ten 80’s tracks - one a year I believe.

Or just go to my music section of the features page and select and curate your own reader experience.

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