Back in school in early ’84 I still had no idea who Madonna was despite the fact that she was ‘burning up’ the charts with her debut album. It took an image of Madonna on the cover of the UK edition of Smash Hits in a lime green sweater for me to eventually take notice of her. By the time I scrounged up enough money to buy her debut album Madonna (1983), Like A Virgin was just beginning to race up the charts. Seriously, I just couldn’t keep up with the Madonna onslaught on the charts and in the media. Almost every girl at school wanted to be Madonna and there wasn’t a month that didn’t pass that she wasn’t on the cover of some sort of music magazine publication. There wasn’t only a dance pop revolution going on in music in the mid ‘80’s with Madonna singlehandedly taking the lead, but she was also at the forefront of bringing sex out in the open often to the dismay of many conservatives. In short, Madonna would go on to transform pop culture with her single-minded drive and fierce independence.

In an impressive (almost) four-decade-long career Madonna has managed to reinvent herself seemingly over and over again. There is no one like her and there will never be anyone like her ever again. In the ‘80s and 90’s she was the biggest pop star of her generation who has outlasted almost everyone. At 60, we are still talking about her and one of those reasons why we still do is because she never seems to shy away from controversy or the spotlight. More recently, she apparently let slip that she believes that today’s music all ‘sounds the same.’ I suppose, it’s typical of Madonna to still be pushing people’s buttons, even after all these years, in an attempt to stay relevant. After all, she is I’m told gearing up to release her first album in three years.

Love her or hate her, and despite some of the cruel age-shaming that Madonna seems to attract nowadays, she is in no hurry to disappear. Late in 2016, Madonna began to fight back and take aim at those critics by saying, “People say I’m controversial. But I think the most controversial thing I have ever done is to stick around.”

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Madonna has appeared on the cover of hundreds of magazines since she first hit the charts in the early ’80’s. This small fraction of Madonna memorabilia I have sporadically collected over the years has become increasingly collectible.

To celebrate the pop icon’s 60th birthday, I hope you will stick around, as I reveal for the purposes of this article a small sample of my favourite songs that have shaped my listening habits from Madonna’s extensive back catalogue. Wait, what! Only a small sample I hear you say. Incredibly, Madonna has released 13 studio albums (and various compilations and soundtracks) and a little over 80 singles and at present I don’t have the patience to rank an extensive list of songs that are all my personal favourite. Over the course of the next few months I will aim to present a short Madonna series that will inevitable throw some light on her influence over me as one of my favourite female artists of all time. Without further ado, please check out these seven worthy classic here below. Honourable mentions to Justify My Love, Like A Virgin, Like A Prayer, Vogue, Secret and Erotica and many others which I will talk about at a later date. Enjoy!

Borderline (1984).

My favourite track on Madonna’s 1983 debut self-titled album is without a doubt Borderline. It was picked as the inescapable follow-up to Holiday which showed an early mature side to Madonna, both lyrically and vocally, as she calls out and feels regret over someone she loves. If you ask me I love how it draws you in instantly from the get-go with its playful introduction but then proceeds to hit you straight up with its sobering message. “Something in the way you love me won’t’ let me be/ I don’t want to be your prisoner, so baby, won’t you set me free”.  

The songs key lyric  “You just keep on pushing my love/ Over the Borderline” is also particular difficult to get out of your head. In short, this is a gem of a song.

Ray of Light (1998).

Somewhere around the mid ‘90s, it was assumed Madonna was finally out of steam. After the release of the musical drama film Evita, some critics and analyst thought Madonna’s best days as a ‘shock factor’ and pop star were finally well behind her. Quietly many of her young fans were also beginning to desert her and began to embrace instead the monumental shift in music, for instance, towards alternative rock. However, Madonna never really went away and released her groundbreaking electronic masterpiece Ray of Light in 1998. Let’s just say it blew everyone’s socks off. It not only marked a new chapter in her illustrious career but showed her contemporaries that she wasn’t about to slow down.

Twenty years on, it still holds up as an epic song. I really like the clanging sound of guitars in its intro and the insanely contagious beat that follows. The song’s lyrics are also pretty cool, especially the line “Faster than the speeding light she’s flying/ Trying to remember where it all began.” Interestingly, Madonna’s voice is pretty amazing too. Apparently, all the vocal training she did for Evita had a positive effect upon her.

Into The Groove (1985).

You couldn’t escape this song even if you tried. It is infectious, lively and arguably Madonna’s greatest song. It was originally released as a non-album single. It appeared in the movie Desperately Seeking Susan as the background music in the disco scene. What’s it about? Madonna once said that the inspiration for the song came her love of dance. “The dance floor was quite a magical place for me. I started off wanting to be a dancer, so that had a lot to do with the song. The freedom that I always feel when I’m dancing, that feeling of inhabiting your body, letting yourself go, expressing yourself through music. I always thought of it as a magical place…”

Human Nature (1995).

The shitstorm that followed the simultaneous release of Madonna’s fifth album Erotica and her controversial book Sex was unprecedented in late 1992. Madonna was herself perplexed by the uproar and came to the conclusion that she was ultimately being punished because she was a successful and powerful single woman. In a 1994 interview Madonna explained, “I feel I’ve been misunderstood. I tried to make a statement about feeling good about yourself and exploring your sexuality, but people took it to mean that everyone should go out on a fuckfest and have sex with everyone, and that I was going to be the leader…”

When it came to the release of her sixth studio album entitled Bedroom Stories, she decided to somewhat tone it down but also exact revenge on her critics via her song Human Nature. The hook sets the initial tone for the song where Madonna mutters almost under her breath “Express yourself, don’t repress yourself”. She would also go on to repeatedly declare in the chorus “And I’m not sorry.”

Madonna best sums up Human Nature in her own words in an exclusive interview she did with Sheryl Garratt in ’94. “It’s my definitive statement in regards to the incredible payback I’ve received for having the nerve to talk about the things that I did in the past few years with my Sex book and my record….It is defensive, absolutely. But it’s also sarcastic, tongue-in-cheek. And I’m not sorry. I do not apologies for any of it.”

To my mind, Human Nature is one of Madonna’s best songs of the ‘90s. It is carried along by an amazing synth undercurrent and knockout bass. I especially love the lyric “Oops…I didn’t know I couldn’t talk about sex”. Pure gold!

Material Girl (1985).

In 1984, Madonna was the hottest female music artist around, with her hit singles Like A Virgin and Material Girl racing up the charts. It is the latter single’s music video that caught everyone’s attention, an homage to Marilyn Monroe’s performance, of the song Diamonds Are A Girl’s Best Friend from the film Gentlemen Prefer Blondes (1953). Madonna was truly inspired by her admiration to imitate Marilyn’s figure-hugging erotic and manipulative song and dance on a bunch of guys too stupid to know otherwise.

Express Yourself (1989).

The reaction that Express Yourself received from all quarters especially women was incredible. I don’t know how many times I heard many of my female friends say “I love that song!” It is the ultimate ‘girl-power’ anthem. The standout lyric surely has to be “Don’t go for second best baby, put yourself to the test…” The music video is equally controversial and outrageously ambitious (apparently it was the most expensive video for its time). In short, the video was Madonna’s salute to the classic film Metropolis (1927).

Holiday (1983).

I read somewhere that Madonna said you would have to pay her millions of dollars to perform Holiday ever again. I’m not sure she should entirely dismiss it as pop trifle yet. After all, it can’t be that bad if she was happy to introduce it to her adoptive twin daughters and post a video of them dancing to it. Holiday was Madonna’s third single from her debut album and stands today as one of her signature songs. Although, it would only peak at No.16 on the Billboard Hot 100, it nonetheless set in motion the beginnings of what would become Madonna mania. In short, Holiday is a celebration of everything that was fun about early ‘80s synth pop.

Photo credit: The collage created from various magazines with Madonna on the cover was assembled and photographed by the author from a personal collection of Madonna memorabilia. I am not the uploader of You Tube clips embedded here.

Posted by Robert Horvat

Robert Horvat is a Melbourne based blogger. He believes that the world is round and that art is one of our most important treasures. He has seen far too many classic films and believes coffee runs through his veins. As a student of history, he favours ancient and medieval history. Music pretty much rules his life and inspires his moods. Favourite artists include The Beatles, Pearl Jam, Garbage and Lana Del Rey.


  1. Great post! My favourite Madonna songs are Borderline, La Isla Bonita, Express Yourself, Get Into The Groove, and Holiday. My parents would often play these songs in the car whenever we went on road trips.


    1. Thank you. There is definitely more to come!


  2. She is an icon. Great post! I’m a compulsive Voguer 😁


  3. Great work. She’s truly an icon with an incredible work ethic.


  4. Wonderful post Robert. I was a huge Madonna fan back in the day (though I haven’t cared for much of her output since 2000). My favorites are Vogue, Take a Bow, Crazy For You, Papa Don’t Preach, Into the Groove, La Isla Bonita, Ray of Light and Live to Tell, but love many many more of her songs.


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