
Madonna picks her five most iconic songs
Ask even the most common music fan for the five most iconic Madonna songs, and it’ll likely be a different answer from each person. There’s arguably no other singular figure quite as defining of pop as Madonna, so defining in fact that she’s never needed a second name, just her star status. Even when the singer herself was asked, her answers stood apart from what might be the expected picks.
Madonna is iconic – there’s no other way to put it. From near enough the second she dropped out of college and ran off to New York, her star was on a course to the top. At first, she just wanted to be a dancer, but when she joined the Breakfast Club, it was clear that she needed to change course. As she wandered through New York’s art scene, dating Jean-Michel Basquiat and spinning her earliest tracks in the city’s underground clubs, Madonna seemed to be a legend right from the very start, mixing the pure pop sensibilities that would make her a commercial smash with a gritty edge that kept her in tune with the bubbling subculture.
Decades on from her breakout with ‘Like a Virgin’, Madonna remains a star on the scale that the world had never seen before and maybe won’t see again. It wasn’t just that her songs were huge, even though they were. But her celebrity was bigger than that, spanning the worlds of film, art and fashion. She was a style icon, helping to define the look of the 1980s especially. The combination of her music and her general cultural presence has made her a household name.
But with so many hits to choose from, scattered across so many eras and decades, it’s tough to decide which of them are the most iconic. However, during an interview with HuffPost, the singer herself had no issue.
First, naturally, came ‘Like a Virgin’, the title track from her 1984 second album. While her debut established her, it was really this track that caught the whole world’s attention following a performance on Top of the Pops. It became her first number-one hit in the US and on the UK dance chart, and the song, with its playfully sexual lyricism, became a sensation.

She then picks two songs from Like A Prayer, her fourth album. The title track obviously makes the list as one of her most defining songs, covered to no end by other artists and drunk singers on karaoke night. Elevating her from a sexy pop kitten into a total pop star, ‘Like A Prayer’ levelled up the scale when it came to Madonna’s compositions and productions, expanding into true anthemic arenas with its gospel edge.
But her pop golden touch remained as she also picked out ‘Express Yourself’ as a track she believes to be one of her most iconic. While this might be one contested by fans who might pick out songs like ‘Hung Up’ or ‘Holiday’ instead, no one could argue that ‘Express Yourself’ is a slice of catchy glory that feels directly responsible for the wave of empowering, feminist pop stars around today as she sings, “Don’t go for second best, baby.”
Her next choice might be a contested one, too, as she picked ‘Ray Of Light’. As the title track of her 1998 album, this marked a moment of all-change for Madonna. The pop she was known for gave way to a more eclectic sound, merging elements of electro, ambient and psychedelic music into her own unique take on something different. ‘Ray Of Light’ launched his new era, which some fans loved, considering the album to be her best work, while others were left behind, still clutching to their 1980s sounds. For Madonna herself, it’s clearly a track she loves.
Her final choice is an inevitable one. It would be impossible to consider Madonna’s most iconic tracks and not include ‘Vogue’. Not only is ‘Vogue’ still her biggest and best-known song, but it has become a timeless queer anthem, bringing the sounds and style of the underground ballroom scene to the masses. Released only as part of the soundtrack for her film I’m Breathless; it’s a song so big that it didn’t even need a proper release or an album to exist on to make it a sensation.