Madonna’s biggest hits: Which ones are our favourites?

What’s your favourite Madonna hit? With 80 official single releases to choose from, it’s no easy decision.

Madonna has become the Queen of Pop by regenerating her image and sound more times than a certain favourite Time Lord of ours, so picking out a particular era is no enviable task.

That said, with her 13th studio album Rebel Heart out on Monday (March 9), Digital Spy staff have managed to choose their favourite Madonna hits from her 30-year-long career so far.

‘Holiday’ (1983) – David Moynihan, Editor
A song as utterly ’80s as Rick Astley or the Pet Shop Boys, ‘Holiday’ is also surely the most evocative theme tune ever created when it comes to packing a suitcase and jetting off for beach cocktails.

Originally released in 1983 on Madonna’s eponymous debut album, the track was written by two members of post-disco band Pure Energy and picked up by the Queen of Pop when her producer rightly recommended it as a surefire smash hit. A feel-good pop giant with an infectious chorus – and the closest thing we have to bottled sunshine.

‘Like A Virgin’ (1984) – Amy Davidson, Music Reporter
It’s the one everyone knows. The one you’re never quite sure is acceptable to sing in front of your mum. The one that saw Madge dance mildly erotically in a wedding dress. Yep, 1984 was the year ‘Like A Virgin’ led from the front, ushering in an album that defined Madonna as more than a mouthpiece for the catchiest pop ditties.

Luring you in with the oldest pop trick in the book – an allusion to sex, ‘Like A Virgin’ soon causes befuddlement with its surprisingly ambiguous lyrics. The track is an irrefutable classic; inviting you to shimmy along to one of the best basslines in pop whilst fruitlessly attempting to hit the high notes of its instantly memorable lyrics (before furrowing your brow in philosophical contemplation if you so desire). With the added genius of Nile Rodgers, ‘Like A Virgin’ marked Madonna’s venture into a period that would seal her fate as a modern icon.

‘Into the Groove’ (1985) – Mayer Nissim, News Editor
‘Into The Groove’ is the quintessential Madonna cocktail. It mixes up equal parts NY Disco (“And you can dance!”), sensuality (“touch my body and move in time”) and top-quality mantraining (“boy, you’ve got to prove…”).

Above all that, it’s a celebration of music and dance (“music can be such a revelation”), a theme Madonna has come back to again and again. Like parent movie Desperately Seeking Susan, the song plays with the idea that you can remake yourself, set free by music.

‘into The Groove’ is a perfect collision of dance and rock and pop, all stuck together with sex and effortless cool. The melody from Madonna and her then-collaborator Steve Bray is appropriately euphoric.

Like David Bowie, Madonna’s greatest asset has always been her ability to not just grab the Zeitgeist, but throttle the ever living hell out of it and stomp on it triumphantly with a stiletto heel ‘cos she’s above it all. There is no better example than ‘Into The Groove’.

‘La Isla Bonita’ (1987) – Lewis Corner, Music Editor
Back in 1986/87, Madonna was dreaming of an escape to the beautiful island of San Pedro. It was the US star’s first foray into the Latin American soundscape; her wistful vocal gently breezing over a warm groove and light Cuban drums. Its mix of traditional Spanish guitar and sharp synths is immediately hypnotic, never failing to transport the listener to a more exotic climate.

The song was originally offered to Michael Jackson by co-writer Patrick Leonard, but the King of Pop wasn’t keen. Instead, the Queen swooped in, switched up the lyrics to suit her own style and went straight to number one in the UK with her serenade to the “beauty and mystery of Latin American people”.

‘Like A Prayer’ (1989) – Morgan Jeffery, TV Editor
The greatness of ‘Like a Prayer’ is often shrouded by the furore surrounding its controversial music video, but strip all that away and what you’re left with is not only unquestionably the best Madonna song, but also one of the best pop songs ever written.

It’s an utterly electrifying tune that begins with a near-isolated vocal from the Queen of Pop before exploding into synth-funk goodness, further incorporating rock and gospel elements, gifting the song a sweep and sense of the epic.

Marking a shift away from the engaging but more basic pop that had been Madonna’s brand – both in its sonic complexity and its more mature lyrical content – ‘Like a Prayer’ is as richly emotional as it is throughly danceable. It remains her pinnacle, some 26 years on.

‘Express Yourself’ (1989) – Kate Goodacre, Chief Sub-Editor
Taken from what’s arguably one of the finest pop albums ever produced, ‘Express Yourself’ is an upbeat, bold, effortless call to arms with a catchy chorus that’s inspired many a pop successor (including Lady Gaga’s ‘Born This Way’).

But behind that soaring, upbeat refrain, there’s a steely message still relevant today, best summed up by Madge herself in a magazine interview from the era: “If you don’t express yourself, if you don’t say what you want, then you’re not going to get it… No-one put the chain around this neck but me. I wrote ‘Express Yourself’ to tell women around the world that pick and choose the best for yourself, before that chain around your neck kills you instead.”

Then, there’s that iconic video, directed by a 26-year-old up-and-comer by the name of David Fincher, fact fans. Further cementing Madonna’s reputation for challenging, attention-grabbing promos, it was a hit with critics and, at the time, the most expensive music video in history.

‘Vogue’ (1990) – Harry Fletcher, Entertainment Reporter
Favourite Madonna track? Has to be ‘Vogue’. A wedding DJ’s go-to record since it was released in 1990: A guaranteed floor-filler. Everything about it – from the slow burning intro, to the irresistible house piano groove of the chorus – is dance music perfection. Madge even shows off her rapping chops towards the end of the track – what more could you want? Strike a pose!

‘Take a Bow’ (1994) – Tom Eames, Entertainment Reporter
Madonna may be better known for her pop bangers ranging from ‘Like a Virgin’ to ‘Hung Up’, and nowadays she seems hell bent on clinging onto her youth by only releasing floorfillers. But, Madge is arguably even better when she shows her vulnerable side.

Taken from her largely forgotten 1994 album Bedtime Stories, ‘Take a Bow’ is a beautiful ballad that took on a more mainstream R&B sound that toned down her act, following on from Erotica and the Sex book. It is an excellent sombre breakup tune that deserves more cred. While it reached number one in the US, it somehow stalled at 16 in the UK.

Honourable mentions also go to her other ballads ‘Oh Father’, ‘You’ll See’ and ‘What It Feels Like For a Girl’, but ‘Take a Bow’ is the most heartfelt and relatable. Plus, it was featured in a classic moment in Friends!

‘Frozen’ (1998) – Sam Rigby, Entertainment Reporter
While the name has been somewhat hijacked by a certain Disney film, there’s only one thing I think of when I hear the word ‘Frozen’ – and that’s Madonna’s ’90s masterpiece. Clocking in at an epic 6:07, the William Orbit-produced track is the perfect blend of ethereal vocals and a dramatic instrumental.

With the help of Orbit, Madonna reached new sonic heights with 1998’s Ray of Light, and ‘Frozen’ saw her showing off a more delicate vocal. Plus, who knew humming could sound so good?

Ask any of my friends and they’ll tell you I’m a sucker for any Madonna ballad, but this remains her greatest. It’s doubtful that she’ll record anything as interesting as ‘Frozen’ again.

‘Don’t Tell Me’ (2000) – Justin Harp, Entertainment Reporter
The minimalism of ‘Don’t Tell Me’ was a most unusual follow-up to Madonna’s bombastic 2000 single ‘Music’. This was a Madonna embracing alt-country guitars in a quiet but emphatic declaration of defiance. Nobody can tell Madonna how she should live her life or who she should love. ‘Don’t Tell Me’ also boasts lyrical sophistication that furthered Madonna’s transition into the elder stateswoman of pop in the era of Britney Spears and Christina Aguilera.

Originally written by Madonna’s brother-in-law Joe Henry for his own solo album, ‘Don’t Tell Me’ was re-shaped by producer Mirwais Ahmadzaï to blend folk with trip-hop and partially re-written by Madonna herself. The track eventually reached the number-four position on both the US and UK singles charts, while also topping Billboard’s Hot Dance Club Songs listing in America.

At the time of its release in 2000, ‘Don’t Tell Me’ was often compared by critics to the work of country rock superstar Sheryl Crow. Those comparisons actually did a disservice to a track that stands out as particularly unique in Madonna’s massive catalogue of hits. And certainly the sight of Madonna wearing a cowboy hat and line dancing in the ‘Don’t Tell Me’ music video still ranks as one of the iconic visuals from her four-decade career.

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