15 Best Madonna Songs of All Time

8. “Justify My Love” – The Immaculate Collection (1990)

There has never been such an atypical number-one radio hit from another pop artist before or since “Justify My Love”. Predominantly spoken-word, “Justify” is a breathy, seductive, and sexual track that many have tried to emulate, but none have ever managed to duplicate—except for, of course, Madonna herself. Written by Lenny Kravitz, the song was inspired by a poem written by Ingrid Chavez. With added lyrics by Madonna, it inaugurated the hyper-sexual theme which dominated her career during the early ’90s.

Although snippets of her aggressive sexuality was apparent in videos for “Like a Prayer”, “Express Yourself”, and “Vogue”, it wasn’t until 1990 when “Justify” (and the accompanying controversial video) was released that Madonna went from stylish suggestion of sexuality to full-fledged explicitness. Although the video is the perfect visual representation for such a sexy tune (directed by Jean-Baptiste Mondino and banned just about everywhere for its frank display of queer sexuality), the song itself stands as one of the best and most innovative singles ever to grace the mainstream public.

It’s an atmospheric tune with a heavy rhythm section, perfectly spoken lyrics, and breathy backing vocals. It paved the way for many female pop artists to follow suit with their own versions of strong sexual subjects—Christina Aguilera’s “Dirrty”, Britney Spears’ “I’m a Slave 4 U”, and Lady Gaga’s… well, Lady Gaga just isn’t sexy. However, although those female pop tartlets tried in earnest to duplicate the sexual power that Madonna displays so effortlessly, there was always an impression that theirs was done with someone behind the scenes pulling strings.

With Madonna, there was never the impression that anyone other than herself was in control. Also check out the equally exotic and wonderful remix entitled “The Beast Within”, where Madonna reads through the Book of Revelations between choruses of her singing, “Wanting / Waiting / Needing / For you / To justify my love.”

7. “Drowned World/Substitute for Love” – Ray of Light (1998)

“Drowned World/Substitute For Love” is the least successful Madonna single listed here. It was never officially released in the US, but managed to crack the UK Top Ten UK and become a hit in most countries across Europe. Its place on this list is due mainly to the fact that — artistically, stylistically, and lyrically — it is her best recording. It is an honest and sincere portrait of a pop icon who saw her fanbase dwindling after the much-despised sexual controversy that plagued her career during the mid-1990s.

Although she managed some great successes during the time after Bedtime Stories and before Ray of Light, most had written her off as being incapable of climbing out of the hole that had she dug herself into. “Ray of Light” was her successful return to the dancefloor, but it was “Drowned World/Substitute for Love” (the perfect opener for the Ray of Light LP) that revealed a much more vulnerable and personal Madonna, stripped of pretense and her shameless “I’m-not-going-to-apologize-for-anything” attitude.

In the song she narrates the choices she had made throughout her career and the sacrifices that came with them. The track proved that when everyone believed Madonna was too full of herself to ever regain the public’s adoration, all she needed was to forget everyone was listening, take a page from some of the most introspective songwriters at the time, and make the kind of music that meant more to her than it did to everyone else. “Drowned World/Substitute for Love” is, in many ways, a sequel to the heartbreaking “Live to Tell”.

6. “Express Yourself” – Like a Prayer (1989)

Madonna was almost always seen as a strong independent woman, but it was “Express Yourself”, the second single from Like a Prayer (1989), that cemented her with that characteristic. For the song, Madonna positioned herself as a feminist preacher summoning her congregation to heed her views on self-expression in love and relationships. Now, the song might sound like a clichéd sentiment, but in the late 1980s, the third wave of feminism was only beginning to enter into the mainstream.

The video — directed by David Fincher and featuring a multitude of various Madonna personas — confused many fans and critics as to the true intention of the song. Was she calling for women to be stronger and independent? If so, why was she chaining herself to a bed and waiting in heat for her male lover to return? Madonna responded to anti-feminist criticisms saying that the song wasn’t about independence, but rather expressing yourself in a relationship with someone you love — not censoring your feelings and not accepting ill-treatment from your lover.

It was a testament for women to take control of their lives and demand the respect and love they deserved from the people who claimed to love them most. And in that proclamation, you can still be sexual, desirable, and super hot like Madonna too. That’s why “Express Yourself” is the perfect heterosexual feminist anthem about self-possession and love.

5. “Music” – Music (2000)

By the time Madonna was ready to release her ninth studio album, she was riding a large wave of comeback-ness. There was no denying that when the lead single “Music” hit (both the Internet and clubs) that Madonna had reclaimed her rightful place on the throne as “Queen of Pop”. “Music” was the first track to be released involving Madonna’s new collaborator Mirwais Ahmadzai — a collaboration which would see its demise much too soon in the failed follow-up to Music, American Life, only three years later.

The song has become an anthem for Madonna, reaching such iconic status as earlier hits like “Holiday”, “Vogue”, and “Into the Groove”. After the confessional Ray of Light, Madonna was ready to dance again, and like no one else can, she proved that her ability to write pure unadulterated mega pop hits was still in full form as she began the third decade of her music career. Not to jinx the success of her latest single “Give Me All Your Luvin'”, but “Music” remains Madonna’s last number one single in the US.

4. “Like a Virgin” – Like a Virgin (1984)

By the time 1984 rolled around, Madonna had released five tracks from her eponymous debut. A pop starlet at the time in deep competition with the critically acclaimed Cyndi Lauper, there wasn’t any real belief that her longevity in the music business would surpass so many pop stars before and after her. When “Like a Virgin” hit, Madonna’s status was elevated to that of pop culture icon. She proved (probably to herself as much as to the rest of the world) that she was more than a simple pop star — she was pushing buttons, exposing belly buttons, dressing in a manner all her own, singing about topics that no one else dared to tread, and loving every minute of it. Conversations over who had more staying power, Madonna or Lauper, began to cease, as Madonna became a household name.

Hailed by many as the song that defined for us who Madonna was (at the time) and would be turning into (in the near future), “Like a Virgin” went on to be her first-ever number-one US hit. Armed with a number of sexual double entendres, both titillating and provocative, she quickly became a strong sexually-charged young woman, unafraid of expressing her desires. And with “Like a Virgin”, Madonna became a liberating mainstream sexual force.

3. “Like a Prayer” – Like a Prayer (1989)

By the time 1988 was over, Madonna decided to appeal to a more mature crowd. Knowing that the fans who had stuck by her throughout the better part of the ’80s were maturing and aging, she decided to take a more personal approach in regards to her infectious pop genre style. Her fourth studio album Like a Prayer featured (at the time) some of the most personal songs of her career. Following her failed marriage to actor Sean Penn and a dismal movie career that was getting worse and worse with every film, Madonna struck back with some of the best music of the late ’80s.

“Like a Prayer” became the most provocative and controversial song and video of her career, and would remain so for about a year until “Justify My Love” was released. Featuring a number of taboo Catholic faux pas (burning crosses, making love to a black saint, juxtaposing religion with race), many cried “blasphemy” at her for her crude and incredibly honest depictions of the kinds of contradictions that almost every sexual little Christian-born boy and girl grew up feeling. She was denounced by the Vatican and lost her Pepsi endorsement deal — who had no clue what she was up to when she agreed to cross-promote the video of “Like a Prayer” with the soda company.

The track is one of her best: musicologically complex and lyrically intricate, here Madonna managed to create a massively successful and deeply complex song that layered on so many concepts it would make other pop artists’ heads spin.

2. “Live to Tell” – True Blue (1986)

“Live to Tell” has held up as the definitive Madonna ballad that perfectly encapsulates who she is as a person, performer, and cultural icon. It is her best ballad, and third-ever US number one single. A heartbreaking chorus has Madonna delicately singing, “A man can tell a thousand lies / I’ve learned my lesson well / Hope I live to tell / The secret I have learned, ’till then / It will burn inside of me.” However, it’s in the bridge when she sings, “If I ran away, I’d never have the strength / To go very far / How could they hear the beating of my heart / Will it grow cold / The secret that I hide, will I grow old / How would they hear / When would they learn / How would they know” that the real crux of the song shines through. Madonna is still a little girl yearning for the greatness and acceptance that so many of us desire.

There’s a vulnerability in “Live to Tell” that Madonna rarely exposes regarding her fears as a human being, living up to the career expectations she’s built for herself, and how she compares to those she admires. Christopher Ciccone has stated that when he wrote his “tell-all” book about what it’s like to be Madonna’s brother, his father commented that Madonna would react badly to the book, not because it painted her as a bitch, but rather as a human. Well, Madonna exposed her humanity 20 years prior in “Live to Tell”. Let’s just ignore that she sullied the beauty and honesty of this song when she climbed up that cross and sang it during the Confessions tour.

1. “Into the Groove” – Desperately Seeking Susan soundtrack (1984)

And so we get to the absolute best Madonna single ever released. “Into the Groove” (written for the film in which she gave her debut feature film performance, Desperately Seeking Susan) is Madonna’s finest single simply because it epitomizes exactly why she’s maintained such a long and significant career… she’s cool. In fact, the song is so cool that even Madonna doesn’t grasp the full degree of coolness it exudes. She has made many remarks about it being a very simple tune that she wrote in less than five minutes, and has never understood why it’s become so popular. Mystified by its serendipitous success, she has tried many times to duplicate the phenomenon that hit with “Into the Groove” — “Vogue”, “Music”, “Deeper and Deeper”, “Where’s the Party?”, “Hung Up”, and “Give it to Me” can all claim to be produced in the hopes of duplicating “Groove’s” brilliance.

Madonna’s inability to understand the coolness of “Groove” (especially that bassline!) represents the fundamental aspect of what makes her so mesmerizing to watch for nearly 30 years now. She is not a flawless icon — she is continuously trying and failing at close to half of everything she does — and yet, it’s this conflation she manages between iconography and humanity that draws us to her. We feel like we could be her, and yet simultaneously know that we never can. Madonna’s music has always felt as though she’s playing on a completely different field than everyone else, and “Into the Groove” is her ultimate anthem, even if she herself doesn’t want to believe it. Although “Holiday” is technically her most popular and mainstream song, recognizable to everyone the world over, “Into the Groove” is the hit that maintains the essence of what makes Madonna so amazing—she’s cooler than you, and you know it.

Editor’s Note: This article was originally published on 8 February 2012. It has reformatted and updated for modern browsers.