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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.
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.
“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.
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.
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.