the sixty best madonna songs

the definitive list of her madgesty's greatest songs

by Michael Cragg
09 August 2018, 12:26pm

image from YouTube

What's the best Madonna song? Is it La Isla Bonita? Holiday? Music? Express Yourself? Frozen? Maybe it's the underrated Living For Love? Or how about Hollywood? Papa Don't Preach? Material Girl? How about Justify My Love? Or Deeper and Deeper? Beautiful Stranger? Like A Virgin?! See, it's tricky isn't it, when one of the greatest popstars of all time has a back catalogue that has basically propped pop up for the last three decades.

I'm not here to say more amazing things about all of Madonna's (mainly) amazing singles, instead, in honour of her 60th birthday, here are Madonna's best 60 album tracks/b-sides/etc. Enjoy it won't you. Remember this list is factually correct. Also, if you CBA to get work through to the bottom of this MDA list, we've prepared a handy spotify playlist:

Madonna (1983)

I Know It
Long live Madonna's debut album vocals that occasionally skirt very close to shrill!

Physical Attraction
It takes 32 seconds before Madonna starts singing. Maybe she was on the loo?

Like A Virgin (1984)

Over and Over
Producer Nile Rodgers unleashes the sort of galloping BPM that feels like a pop panic attack.

Madonna's tribute to Motown and doo-wop. More songs should be called Shoo-Bee-Doo to be honest.

Sounds like it was created using a Fisher Price keyboard, i.e. it's low-key amazing.

True Blue (1986)

White Heat
Dedicated to actor James Cagney, who is sampled at the beginning of the song.

Where's The Party
Inspired by Madonna's desire to just have a nice dance when things get a bit much. “I say, 'Wait a minute, I'm supposed to be having a good time here, so where's the party?' It doesn't have to be this way. I can still enjoy life,” she said of the song's inspiration.

Jimmy Jimmy
Another song about a film star, this time James Dean, who Madonna used to dream lived in the same neighbourhood as her.

Love Makes The World Go Round
This skipping synth-popper was originally performed at Live Aid in 1985 and was intended as the album's first single. It wasn't, obviously.

Who's That Girl (1987)

Can't Stop
A song about becoming ever so slightly obsessed with someone you think is pretty fit. Relatable.

Like A Prayer (1989)

Love Song feat. Prince
Prince played guitar on three songs on Like A Prayer, but remained uncredited. He's very obviously all over this oddity, which Madonna finished remotely because she couldn't stand Minneapolis.

Till Death Us Do Part
Originally called 'State of Matrimony', the surprisingly jaunty Til Death Us Do Part is about the dissolution of her marriage to Sean Penn.

Promise To Try
Perhaps the saddest entry in the Madonna canon of songs about her late mother.

Pray for Spanish Eyes
Unquestionably one of her best ballads, which is saying a lot.

Supernatural (b-side to Cherish)
Originally written for True Blue, the rock-tinged Supernatural eventually wound up as a b-side to 1989's Cherish.

I'm Breathless (1990)

Something to Remember
A sumptuous ballad written for the soundtrack to the woeful Dick Tracey film. Also gave its name to 1995's ballad collection.

Sooner Or Later
This Stephen Sondheim-written jazz-fest won the Best Original Song Oscar in 1991. Madonna took a date to the event, you might have heard of him -- Michael Jackson was his name.

Erotica (1992)

Imagine keeping Madonna waiting though. Not a good idea.

Thief of Hearts
A sonic warning to anyone brave enough to try and steal Madonna's man. "Bitch!/Which leg do you want me to break?" she snaps after the sound of broken glass opens the song. Blimey.

In This Life
Erotica's emotional centrepiece, written as a tribute to friends Madonna had lost to AIDS.

Secret Garden
A lovely, jazz-inflected ode to “the secret place where she could enjoy herself”. Many assumed she meant her vagina.

Bedtime Stories (1994)

A reference to her past? Check. Honeyed backing vocals? Check. A whiff of Soul II Soul? Erm, check.

In which Madge quotes Walt Whitman's poem Vocalism over a Herbie Hancock sample.

Inside of Me
You want breathy vocals, an Aaliyah sample and lyrics that sound like they could be about sex but are probably a bit more metaphorical than that? Great, here you go.

Ray of Light (1998)

Like so much of the Ray of Light album, Skin sounds like it was recorded underwater. It's also incredibly rehydrating.

Sky Fits Heaven
A gently pulsating ode to spiritual enlightenment that also references the Björk-written Bedtime Story. Elements of the lyrics are taken from Max Blagg's poem What Fits? which was also used in a 1993 Gap advert.

To Have and Not To Hold
To Have and Not To Hold is rumoured to be the inspiration behind Shakespeare's line, "To be or not to be".

Little Star
A trip-hop-esque ode to her daughter Lourdes. Imagine -- IMAGINE -- Madonna being your mum.

Has To Be
This gentle, sighing ballad -- “there must be someone out there, there just has to be” -- was only available on the Japanese version of Ray of Light.

Music (2000)

Impressive Instant
Altogether now: "I like to singy, singy, singy, like a bird on a wingy, wingy, wingy". This batshit electronic squiggle of a song was actually released as a club-only promo single but who cares right?

I Deserve It
“This guy was meant for me, and I was meant for him/ This guy was dreamt for me, and I was dreamt for him”. And she was married to fake gangster Guy Ritchie at the time, do you see?!

Nobody's Perfect
An auto-tuned ballad that flutters and struts in all the right places.

Paradise (Not For Me)
Also appears on producer Mirwais's Production album.

A lovely, lilting folk song given a slight electronic makeover by William Orbit.

American Life (2003)

Absolutely should have been a single, I'm sorry. Altogether now: “and I know that love will change us forever”.

X-static Process
Madonna plus guitars is always a bit hit and miss but this Stuart Price-assisted rumination on relationship woes is one of her top 5 hidden gems, please don't @ me.

Mother and Father
That rare thing: A pulsating electronic banger about a dearly departed parent.

American Life (remix feat Missy Elliott)
So you can polish a turd. Notable for Missy rapping “hotter than fat bitches dancing in a sweater”.

It's So Cool (original 2002 version)
Originally written during the American Life sessions, It's So Cool was eventually re-worked by Paul Oakenfold for the iTunes version of greatest hits compilation GHV2. The original leaked version is far superior.

Confessions on a Dance Floor (2005)

Future Lover
One of the first three songs written for the album in Stuart Price's loft. If you're impatient, it properly goes off after 90 seconds.

Forbidden Love
This isn't the only Madonna song called Forbidden Love. There's one on Bedtime Stories too. This one's better mind you. Of the use of the same song title, the Me Against The Music hitmaker said: “I mean, if I'm going to plagiarise somebody, it might as well be me, right?”

Like It Or Not
Produced by Bloodshy & Avant who helped create Britney's Toxic, which means they're basically pop royalty.

The lyrics interpolate The Police's stalker anthem Every Breath You Take.

Hard Candy (2008)

There are a lot of bad moments on unfairly maligned 2008's sickly sweet opus Hard Candy, but this Neptune's banger isn't one of them.

She's Not Me
During 2012's MDNA tour, Madonna segued Express Yourself into Lady Gaga's quite similar Born This Way before really hammering home the point with a snippet of She's Not Me. Amazing.

Beat Goes On
There's a version of this shimmering disco-tinged bop that doesn't feature Kanye West. That version is better.

Spanish Lesson
Madonna bloody loves Spain doesn't she.

Devil Wouldn't Recognise You
A Justin Timberlake-assisted mid-tempo that sounds like a FutureSex/LoveSounds off-cut. In a good way.

MDNA (2012)

I'm A Sinner
There are also some stinkers on MDNA. The William Orbit-produced I'm A Sinner, with its nods to Beautiful Stranger, is one of the highlights thank goodness.

Love Spent
Opens with a banjo but please don't let that put you off.

Falling Free
A properly underrated subtle ballad moment on a album that tries way too hard.

Beautiful Killer
Weirdly this song didn't make the main album, which is even more odd when you realise a song by Mika did.

I Fucked Up
Try “I fucked up, I made a mistake” next time you buy skimmed instead of semi-skimmed milk.

Rebel Heart (2015)

Devil Pray
About the lure of temptation. Features a line about a typical night round mine: “we can do drugs, and we can smoke weed and we can drink whiskey”.

Joan of Arc
One of Rebel Heart's softer moments, it features Madonna saying that yes she's a strong badass but sometimes she too feels a bit shitty.

HeartBreakCity is on the M4, just past junction three.

Inside Out
Yes the line “show me yours and I'll show you mine” does almost ruin it.

Best Night
Once again, Madonna references herself, this time reciting the lyrics to Justify My Love on this Diplo co-production.

Beautiful Scars
Frequent co-writer Rick Nowels returns for this genuinely lovely, BloodPop co-produced bop.

Rebel Heart (original)
Some terrible bugger leaked loads of songs from the Rebel Heart sessions in advance of it even being announced, including the title track. Pissed off, Madonna reworked it, the result being infinitely worse than the one that ended up on the album.

So that's it, our 60 favourite Madonna songs -- some killer, some thriller. What are your favourites?

ray of light