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Madonna has dominated the radio and video airwaves for quite some time, and although the moniker of “King of Pop” is firmly affixed to Michael Jackson, “Queen of Pop” gets bounced around to every new fluffy pop tartlet who claims to integrate music and fashion like it’s something that’s never been done before

This compendium of the most significant Madonna singles ever attempts to traverse the vast terrain of subjects, styles, and themes that Madonna gravitates towards most across her long career. Before I (and a friend) began shortlisting Madonna singles, we decided that in order to do this list justice we would need to determine the most significant themes in Madonna’s body of work, so as not to end up with 15 dance songs, 15 ballads, or 15 random songs. The songs on this list aren’t necessarily characterized by just how huge the single was in terms of critical reception or chart performance, but rather how significant they are (without potentially repeating themselves) in helping to shape this iconic woman.

Madonna has always been, first and foremost, a dance artist. There is no denying that her music is almost always catchy and meant to get you to step to the beat. Some of her most popular songs are her simplest — “Into the Groove”, “Holiday”, “Vogue”, “Hung Up” — and the list could literally go on and on. So, the pop/dance theme was a major consideration when making this countdown. Madonna has also never shied away from integrating elements of her private life that she feels comfortable divulging to the media-hungry public.

Although her more personal tracks don’t always stand up as some of her best, it is undeniable that at times Madonna has managed to compete with some of the most introspective singer/songwriters around. Sexuality and gender have also been big recurring themes in her music — image being closely tied to the former and power integrating with the latter. In addition to being a powerful and sexual female, Madonna has oftentimes — more so in her image and personal messages — evoked some controversial and provocative interpretations of religion, be it Kabbalah, Christianity, or Judaism. Wrapped in her bombastic persona is her penchant to be provocative and controversial.

There are of course a number of other significant thematic recurrences in her music, but when distilling Madge down to her essence, she comes up as a powerful and sexual female dance/pop artist with the capacity to evoke some insightful and introspective songs from time to time. She’s more than just fluff, she’s more than just sexual, she’s more than just female, and she’s more than just powerful: she is Madonna!

15. “Take a Bow” – Bedtime Stories (1994)
There was a time in the early 1990s when Madonna was hated! You probably don’t remember, but she was the target of so many “$l*t” jokes, being ridiculed for her obscenities and lambasted for presenting herself as a down-right whore. In less than three years she released two explicit music videos (“Justify My Love” and “Erotica”) both banned from MTV airplay, published a sex-themed coffee table book, released a full-length sex-themed album (Erotica), played the key role in a raunchy erotic thriller (Body of Evidence), and made a surprise appearance at the 1992 Gaultier fashion show where she removed her jacket to reveal her exposed breasts underneath. The mainstream public saw a lot of Madonna being naked, and they hated her for being so forthright with her sexuality.

Finally, in 1994 she put away the explicitness that characterized her for the first few years of the 1990s and became more suggestive. Oftentimes dismissed for its occasionally schmaltzy sentiments, “Take a Bow” was a huge success for Madonna, a track accented perfectly by the fantastic video (produced as an audition tape for the lead role in the film Evita, which she would later go on to win). “Take a Bow” features a more demure Madonna, confident in her termination of a doomed relationship, and the music is accented by characteristically Asian orchestration and lovely poetic lyrics.

Also, instead of shying away from her sexuality completely, the video features the scantily dressed singer making love to a television—a scene just as explicit as her previous work, but this time more poignant and significant. Madonna quickly learned that the way back into the public’s collective hearts was to focus more attention on the music than on the frankness of her sexual image.

14. “Ray of Light” – Ray of Light (1998)
Madonna rode a pretty high wave for awhile, finally earning some of the respect of Hollywood (she so desperately sought) for turning out a wonderful performance as Eva Peron in the film version of Evita. Although she was somewhat praised for that role, even winning a Golden Globe for Best Actress in a Comedy or Musical, she was still slightly on the outs with the music buying public, who hadn’t forgotten her earlier raunchy ways and were more and more moving away from dance/pop tunes (grunge being particularly huge at this point).

So, at a time when Madonna was beginning to lose her musical significance, she searched inwardly and released arguably her best album to date—1998’s Ray of Light. The album was magnificently produced by William Orbit (whom she has re-recruited for her soon-to-be-released MDNA album), and beautifully written with her most intimate and poetic lyrics. The title track characterized the “new” Madonna that took the world by storm, and won back the hearts of those who had written her off as having reached the end of her music career.

Up until Ray of Light, Madonna had always kept the public at arm’s length, never fully granting access into her spiritual and personal side. Borrowing elements from the growing popularity of underground electronica, “Ray of Light” revealed that side of Madonna that fans and non-fans had never been exposed to before, and was received with open arms from her adoring public. Madonna was back!

13. “Who’s That Girl” — Who’s That Girl soundtrack (1987)
There is a side to Madonna’s career that we would all like to better forget. However, it is undeniably an aspect of what has made her such a flawed cultural icon. She’s not magnificent at everything she does, which is part of what elevates her above most other frivolous pop acts, but everything she does is done on as grandeur a scale as she can muster. “Who’s That Girl” was written solely for the purpose of promoting her lead role in the film of the same name—a film too quickly dismissed, if you ask me. Although the film was met with dismal critical reception and an even worse box-office performance, the song went on to be her second simultaneous number one hit in the US, UK, and Canada, second to “Papa Don’t Preach” only a few years earlier.

“Who’s That Girl”, in many ways, represents two significant aspects of Madonna’s career: 1. The side that sees her desperately trying to win the admiration of fellow thespians;and 2. Her ability to write and record wonderful thematic songs that oftentimes eclipse the movie for which they were written (ranging from “Crazy For You” for Vision Quest to her recent offering “Masterpiece”, for W.E.). If “Who’s That Girl” and the subsequent Madonna songs from that soundtrack are any indication of how she can deftly capture the theme and feel of a film, one can only wonder what she could do scoring an entire soundtrack. Occasionally overlooked when compiling “best of Madonna” lists, “Who’s That Girl” is an insta-party from the moment it begins.

12. “Vogue” — I’m Breathless (1990)
What has kept Madonna afloat for so many years is her knack to pick out emerging trends happening in the fringes of culture and bring them into the limelight. For this track and its wonderful video, Madonna borrowed elements from the vogueing craze that was making its way through many gay clubs. Originally intended as a b-side for the single “Keep It Together”, record executives deemed the song much too good to be wasted as a b-side, and thank God they did! “Vogue” was released as a lead single for Madonna’s half-album/half-soundtrack I’m Breathless (Music from and Inspired by the film Dick Tracy), going on to become her biggest hit at the time.

The significance of “Vogue” however, cannot be isolated on the merits and quality of the song itself. It’s undeniable that Madonna’s cultural icon status is heavily influenced by her visual imagery, which perfectly complements (and sometimes overshadows) the audio. This symbiosis between the visual and the aural is none more so exemplified than in the success of “Vogue”: not only was the promo (directed by David Fincher) a commercial success, but the tune itself glorifies and epitomizes the synergy and importance between combining imagery and audio. As the song and video have gone on to become anthems of both Madonna and fashion/style trends, “Vogue” is delivered with all the class, attitude, and panache that made Madonna so world renowned.

11. “Holiday” – Madonna (1983)
Needing a radio-ready dance hit for her debut album, “Holiday” was given to Madonna by then co-collaborator and producer John “Jellybean” Benitez, who had discovered the demo floating around for some time (having been rejected by many pop acts to whom it was offered to). “Holiday” was Madonna’s first hit single, and though it never really reaching the coveted top spot, it nonetheless went on to become the staple party song played at every wedding ever! It perfectly characterizes the beginnings of a monumental career that few will ever know.

Quite arguably Madonna’s most recognizable and popular track, the appeal of “Holiday” traverses across a variety of music lovers who both love and revile her. Those who claim to not own a Madonna album will most likely admit to enjoying this simple tune when it’s pumped up in a crowded club or social event. It’s too infectious to not dance and sing along too, and too iconic to ignore. When the opening melody of this cross-genre hit begins, you know it’s a holiday.

10. “Hung Up” – Confessions on a Dancefloor (2005)
Two years after the disastrous American Life saw her potentially catapulting of out of the limelight for good, Madonna struck back against all those who loathed that album. Instead of facing it dead on (the way she did 10 years previous with “Human Nature” from Bedtime Stories), she decided to step lightly around the topic, for America had become significantly less forgiving than ever before and her brazen “absolutely no regrets” attitude wouldn’t have gone over so well. “Hung Up” struck big. It rode the wave of speculation that surrounded the release of the phenomenal Confessions on a Dancefloor, which saw Madonna return to her disco roots.

But wait! Madonna was never a disco queen — she came out in the early 1980s with much more rock/pop-inspired dance numbers to ever be considered disco. Ah, see, she fooled us all. Confessions is much more of a prequel to her debut — a pre-Madonna if you will. “Hung Up” was inspired by the music that Madonna enjoyed during her early twenties frequenting the Danceteria in New York mashed together with her love of ABBA.

“Hung Up” is exceptional for a number of reasons: 1. It marks the second time in history that ABBA has agreed to let another artist sample their music, citing nothing but admiration and respect for Madonna; 2. It is the biggest global hit Madonna has ever had (to date), earning her a place in the Guinness Book of World Records; 3. It has sold more than nine million copies worldwide; 4. It’s kick-ass; and 5. And, it proves that even after 21 years Madonna can still dominate pop/dance charts the world over. Rocking Farrah-hair and a leotard in the video, “Hung Up” stands as one of the best post 1990s Madonna singles.

9. “Crazy for You” – Vision Quest soundtrack (1985)
Madonna was only two albums into her career when she recorded this cu from the Vision Quest soundtrack. Up until this point, she had only one other ballad under her belt—the failed “Love Don’t Live Here Anymore” from Like a Virgin — but we’re not going to talk about that. “Crazy for You” marked a new direction in which the pop-artiste would excel. Here Madonna proved that she still possessed all of the same charisma and persona in a slowed-down sultry and subdued offering.

The song went on to transcend its appeal beyond the already loyal Madonna fans by reaching those who had dismissed the singer too early on. Although Madonna didn’t have a hand in writing the ballad, it stings of her presence. Her delivery suggests a stronger sense of yearning and desire that a lesser performer would have surely fumbled over. It was also the high-school slow dance song for many, many years to come. Who among you can tell me that you don’t immediately scan the room for someone to dance with when you hear the opening drum fill and orchestration?

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.

(Source: PopMatters)