Madonna’s 20 best songs

The icon recently turned 59

Being a total don comes naturally to Madonna, who’s spent the last 34 years redefining the rules, making brilliant music, and shooting unmissable videos to accompany it all. Let’s take a look at some of her best songs.

‘Into The Groove’ (1985)

This straight-up bop soundtracked the 1985 film Desperately Seeking Susan, in which Madonna played the titular Susan Thomas. It’s about dancing, of course.

Key lyric: Only when I’m dancing can I feel this free

‘4 Minutes’ (2008)

2008 found Madonna flipping to the ‘Ti’ section of her phonebook to rope in Timbaland and Justin Timberlake for an apoca-jam of epic proportions. As if the carpe diem message weren’t hitting you hard enough already, she and JT also hammered the point home in the video by dancing around in front of a massive countdown timer.
Key lyric: Tick tock

‘Take a Bow’ (1994)

Madge works a bit of Shakespeare into this contemplative and downbeat soother from ‘Bedtime Stories’. At first it sounds like a comparison between a broken relationship and a curtain call, but the video pivots the story to paint the bad guy as a deadly matador.
Key lyric: You took my love for granted, why oh why? The show is over, say good-bye.

‘Material Girl’ (1984)

Boasting one of the most iconic synth lines ever, ‘Material Girl’ has a Marilyn Monroe-inspired video, and entirely unironic lyrics about loving, erm, stuff. In ’86 Madonna said: “You are attracted to men who have material things because that’s what pays the rents and buys you furs. That’s the security. That lasts longer than emotions.”
Key lyric:
If they don’t give me proper credit I just walk away 

‘Deeper and Deeper’ (1992)

‘Erotica”s head-over-heels slice of dance-pop preaches pure “love is love” and includes a lyrical callback to ‘Vogue’, the single that preceded it. Don’t miss the bit in the middle, which we’re cautiously terming a ‘Flamenco drop’.
Key lyric: 
I can’t help falling in love – I fall deeper and deeper the further I go.”

‘Don’t Tell Me’

Arguably better than ‘Music’ – the title track from Madonna’s cowboy-style 2000 album – ‘Don’t Tell Me’ is a country-dance experiment that boogies around over a twanging guitar line, gobby synth, and bits of vocoder noise – and strangely appropriate lyrics about the importance of following your instincts.

Key lyric: Don’t ever tell me to stop.”

‘La Isla Bonita’ (1986)

This Latin-inspired melody, written originally for Michael Jackson, instead went to Madonna for her album ‘True Blue’ – and in it she pays tribute to samba, San Pedro, and the chill life.

Key lyric: Last night I dreamt of San Pedro… It all seems like yesterday, not far away“.

‘Holiday’ (1983)

Thanks to contemporary homages like Shura’s ‘Indecision’, we’re still feeling the influence of this funky vacation bop, whose video handily doubles as the perfect out-of-office autoreply. Sadly Madonna herself doesn’t actually like it all that much any more, saying in 2008 that she didn’t want to ever sing it again “unless somebody paid me, like, $30 million or something.”
Key lyric: Put your troubles down – it’s time to celebrate.”

‘Music’ (2000)

You can accurately date this song by any number of factors: its drum-machine claps, its electropop borps, its strange music-video cameo from Ali G, its trip to the strip club, or even Madonna’s cowboy-hat bling. But none of that stops it from being a total banger.
Key lyric: Music makes the bourgeoisie and the rebel“.

‘Borderline’ (1983)

Some silky smooth synths introduce this bouncy, complex track from Madonna’s eponymous debut. In the lyrics she mourns her dissatisfaction in love; in the video she takes it out on her useless boyfriends.
Key lyric: 
Don’t you know you drive me crazy? You just keep on pushing my love over the borderline“.

‘Beautiful Stranger’ (1999)

For a while it looked like this pop smash would permanently be associated with Austin Powers. Luckily, it’s been covered brilliantly by DMA’s and The Big Moon in recent years, taking on a new form in the collective memory as a banging rock anthem.
Key lyric: To know you is to love you

‘Express Yourself’ (1989)

Not just a tune, this five-minute anthem blasts gender roles using oppressive imagery from Metropolis, and at the time its budget of $5m made it the most expensive music video ever.
Key lyric:Long stem roses are the way to your heart but he needs to start with your head“.

‘Frozen’ (1998)

Essentially a sad, goth version of All Saints’ best song ‘Pure Shores’ – which actually sampled this very song – ‘Frozen’ is full of longing “mmm”s, and its video encompassed Evanescence’s entire aesthetic better than Evanescence ever did. 10/10.
Key lyric:If I could melt your heart we’d never be apart

‘Justify My Love’ (1990)

As heavily censored as notorious sex jams like George Michael’s ‘I Want Your Sex’ and Donna Summer’s ‘Love To Love You’, this heavy-breathing song got banned by most networks for its depiction of a threesome, and its sprinkling of sadomasochism. It accordingly topped the charts in the US, Canada and, of course, Finland.
Key lyric:I want to know you. Not like that – I don’t want to be your mother.

‘Ray of Light’ (1998)

Madonna dips into Eurodance and trance with this hazy, effects-laden banger for the ages, which peaks just after the 4.20 mark. Is there a playlist this song wouldn’t improve?
Key lyric: Faster than the speeding light she’s flying, trying to remember where it all began“.

‘True Blue’ (1986)

So ’80s it hurts, ‘True Blue’ has an upbeat pop melody and crushing lyrics about love gone wrong. Naturally, it topped the UK singles chart.
Key lyric: Your heart fits me like a glove and I’m going to be true blue“.

‘Like A Virgin’ (1984)

Filming the video for this unstoppable single in a centre of Catholic conservatism – Venice, specifically – Madonna maxed out her playful contrast of innocence and flirtiness, certifying her status as a masterful pop icon.
Key lyric: Like a virgin, feels so good inside when you hold me

‘Hung Up’ (2005)

Beautifully sampling that arpeggiated bit from Abba’s ‘Gimme Gimme Gimme’, breakup banger ‘Hung Up’ is quite easily the best Madonna song this side of the Millennium, taking the Number One spot in 41 countries. In its instantly recognisable video, Madge dances in a neon-pink leotard while people do some #parkour in London. It was 2005, after all.
Key lyric: Every little thing that you say or do, I’m hung up on you“.

‘Vogue’ (1990)

The song that took voguing mainstream was totally open about its inspirations in the fashion world, name-checking icons and idols like Greta Garbo, Marilyn Monroe and Bette Davis, and homaging the fashion photography of Horst P Horst in its video.
Key lyric: Come on, vogue – let your body move to the music

‘Like A Prayer’ (1989)

Gospel and pop join forces here, forming a praiseworthy confection of sexual and religious ecstasy. Its video, featuring shots of the KKK’s burning crosses, was one of Madonna’s most controversial, with vocal condemnation from the Vatican and many other religious groups. Bitch, she’s Madonna.
Key lyric: It’s like a little prayer, I’m down on my knees, I want to take you there“.

What’s your favourite Madonna song? Let us know in the comments.