Deeper and deeper: Madonna's hidden gems and deep cuts you need in your life
We all know Madonna's huge hits, the 13 Number 1s (a chart record - 59 more incredible chart facts here), and her signature tunes, but what about the rest?
With a collection of work like Madonna's, it's only natural some songs – even those released as singles – would be overlooked. Some will be fan favourites, unheard recordings, or songs you never even knew you couldn't live without.
As the Queen of Pop celebrates her 60th birthday, let's go deeper and deeper into the songs that made Madonna. We've compiled the songs into a playlist at the bottom of the page.
Is Angel Madonna's most underrated single? Very possibly. Despite being a Top 5 hit in 1986, this Like A Virgin cut never had a video, doesn't make it into her live shows, and is generally forgotten by even the most devoted stans. This is a travesty. Showing a softer side to Madonna, Angel's lyrics perfectly describe overpowering, all-consuming adoration for a lover. The 12" version features disco legend Nile Rodgers, who produced the album, among a crowd chanting "Madonna! Madonna!" and is a thing of wonder.
Till Death Do Us Part
Often, and justifiably, lauded as the best Madonna single that never was, on first listen the raw and heartbreaking lyrics seem at odds with the upbeat, frenetic, jumpy and urgent backing track, until you realise that's what Madonna is trying to convey: the outer veneer of the perfect, happy marriage with the murky, violent truth lurking beneath the surface. It's harrowing and haunting, yet a total tune, which makes it all the more unsettling. A must-listen for anyone who thinks Madonna can't do "deep".
Madonna's first ever single doesn't get that much attention these days, but when she revived it at a live performance to mark the release of Confessions on a Dance Floor in 2005, the song had just as much energy as it first did over 20 years earlier.
This noisy, stilted electronic bruiser is the result of Madonna and Benny Benassi locking horns. Madonna has said this was the most difficult to write of all the songs on MDNA, and it shows, but she pulled it off: she demonstrates a lyrical flair here that's maybe missing from a lot of the rest of the album.
Dress You Up
Yet another overlooked single from Like A Virgin, Madonna seems to be making amends – she included it on her third greatest hits album Celebration and has performed it live in recent years after over 20 years of ignoring it. Comparing her love to a shopping trip to Topman, its lyrics are smart and sexy and very Madonna, and it went Top 5 in 1986. Again, no official video, just a live performance. Sigh.
Express Yourself (original version)
We can hear your necks snapping back in horror at this one, but stay with us! The Like A Prayer album version of Express Yourself never gets the credit it deserves. Shep Pettibone's (very good) housey remix nabbed its place in history when it accompanied the iconic video, and of course was the inspiration for the brilliant Vogue. But the album version was a note-perfect '80s soul KC and the Sunshine Band pastiche that kind of matches the song's motivational message better.
This B-side shows Madonna contemplating having sex with, and becoming pregnant by, a ghost. What's not to like? Originally heavy on guitars, it was remixed into a very '90s housey hip-hop bop by Sly & Robbie for the Red, Hot & Dance charity album.
All the Confessions singles went Top 10, but as an album it's pretty much unique among Madonna's back catalogue that pretty much every track had single potential. Of them all, Future Lovers seems like the hit that never was. It's an intoxicating rush of motivational disco, which takes its cue from Donna Summer's I Feel Love. In fact, the version of the song which opened Madonna's Confessions Tour and interpolates Donna's hit should be considered definitive.
Madonna's Rebel Heart album contained her poppiest efforts in a long while, and while the album may have lacked cohesion, it certainly threw out some excellent curveballs, including this mystic BloodPop-produced tune. Madonna tries out all her best automobile metaphors on this summery song.
Nope, not a typo! We all know Erotica, of course, with that infamous video of Madonna hitchhiking with no clothes on, but did you know about this version, which was included with her controversial SEX book? It features rather different lyrics to the album version – mostly about Madonna hinting she's going to tie you up with bin bags and bang the crap out of you – and the backing track is stripped back and wonderfully gloomy. It's also worth checking out William Orbit's remix, which predates their work together on Ray of Light.
Promise to Try
Madonna's ballads often get short shrift, Crazy for You and Live to Tell aside, but Promise to Try shows off her talents. It's mainly just a piano, Madge, a whole bucket of emotions and the eerie presence of her late mother. Don't listen to it drunk: it will destroy you.
This song got to Number 3 in 1991! 3! And who remembers it? Nobody. And that's a shame because it's really great. Madonna does her best talk-singing in the verses – with some of her most impressive lyrics – like she's reciting poetry, before letting rip in the chorus of this Immaculate Collection track. It's made all the better by the fact she's clearly a bit hoarse from her gruelling Blond Ambition Tour the year before.
Thief of Hearts
Back in 1992, repeating the word "bitch" throughout a song was quite shocking, and Madonna really goes for it here, by kidnapping and possibly maiming a woman who stole her man. Added bonus is the sound effect of Madonna chewing her way through a whole packet of Juicy Fruit.
Back in Business
Madonna was certainly unpredictable in 1990. By the end of the year she'd be tearing about hotel corridors in her lingerie for Justify My Love, but during the summer she reinvented herself as a big band singer from the 1930s, thanks to her role in Dick Tracy. Of the songs "inspired by" the movie on her album I'm Breathless, this tale of mobster revenge is the best. The backing vocals trilled in perfect gangster parody accents are priceless.
I'm Going Bananas
Another one from I'm Breathless that she definitely wouldn't get away with today. It uses some rather problematic terms for impaired mental health, and features Madonna singing in an accent that is at the very least culturally insensitive. And yet, despite being a garbage fire on paper, I'm Going Bananas is a riotous, Latin explosion that shows off Madonna's kooky side. Thankfully, it's short.
Third single off Erotica, this got to Number 10 and shows off Madonna's storytelling abilities in its (rather depressing) lyrics. Her performance of Bad Girl on Saturday Night Live is widely thought to be one of her very best live vocals.
Love Tried to Welcome Me
Madonna is great at doing miserable, even though she doesn't wheel out the melancholy that often. From one of her most overlooked albums, Bedtime Stories, Love Tried to Welcome Me is almost a sequel to Bad Girl, an atmospheric, epic, emotive ballad. It also demonstrates Madonna's clairvoyant skills: the lyric "Instead of spring, it's always winter" is a clear reference to 2018's "Beast from the East" weather phenomenon which froze the UK out of our minds until April.
Look through all of Madonna's single and album artwork:
Substitute for Love
A Number 10 hit in 1999, and released in very few countries, this is yet another of Madonna's overlooked slowies. She looks amazing in the video and it's one of the few songs about the perils of fame that doesn't have you reaching for the tiniest violins in the world.
This zingy bonus track from the Confessions era features Madge musing on what it would be like to be President, among other fantasies. Maybe she'll do it one day, and during her inauguration can vogue out of the White House to this bop.
Trippy electronica! Death! Madonna on top vocal form! More death! The closing track of the Ray of Light album is a brilliant downer.
This laidback, atmospheric duet with Ricky Martin mixes acoustic and electronic and its abrupt finish leaves you wanting more – just the way Madonna likes it.
Like an Angel Passing Through My Room
Yes, that's right. We said it. Rarer than hen's teeth – although a leaked demo is online – Madonna tackled the closing track of ABBA's final studio album The Visitors in the sessions for Music. And you know what? It's good. William Orbit's lullaby-esque production and Madonna's restrained vocals (she sounds a bit nervous, actually) certainly do the song justice.
It still hurts, tbh, that this Music album track was never an official single. It's a pulsating, sweaty, relentless dance banger in which Madonna compares herself to a bird, using the most perfect couplet in pop: "singy singy singy/wingy wingy wingy". It would've been Number 1 for centuries, right?
Paradise (Not For Me)
Madge got French and moody on this Mirwais-produced atmospheric tune. She did a great version of it on her Confessions Tour – not long after leaping down from a huge crucifix, you know what she's like – and it remains one of her better midtempos.
Yes, OK, she's banging on about fame again but this is a kind of hopeful, wistful tale of motherhood, ageing and still having more to give. When Mirwais and Madonna get together, there are always fireworks, but it does seem they gel best on contemplative tracks like this.
Hard Candy gets a bad rap as an album, and seemed like something of a misstep after the euphoric and floor-filling Confessions, but Madge hates to repeat herself. Among the best songs is this Pharrell-produced bop, on which Madonna regains her youthful innocence and sounds much freer than she does on any other song on Hard Candy.
Some would argue the leaked demo version of the song – which was like Madonna doing vulnerable ABBA-esque pop – was the better version. And they are right. However, the Rebel Heart final edit has its pluses, and carries off the '90s house throwback vibe rather more successfully than the album's lead single Living for Love did.
As collaborator Diplo said, this song should've been a hit and may well have been had another artist been singing it. She looked epic in the video too.
Listen to a playlist of our selection of Madonna's hidden gems, plus some you suggested! Let's go FULL MADGE.