For this week’s article, I thought I’d go over a lesser-known, relatively unpopular topic. Then I decided to throw that out the window and go for the biggest female music icon in history. (No, not Rebecca Black. Although you have to get down on Fridays. It’s the law.) Break out your lace tops, your fishnets, and your copious amounts of crucifixes.
Madonna Louise Ciccone was born in 1958 in Bay City, Michigan to an Italian-American father and a French-Canadian mother before being raised in the Detroit suburbs. As her mother was also named “Madonna”, the family called her “Little Nonnie” for the first years of her life. Tragedy struck the young Madonna at the age of five when her mother died of cancer; her father remarried three years later to the family’s housekeeper, irreparably damaging Madonna’s relationship with him. Despite the adversity and the tension in the home, Madonna was a stellar student, earning straight A’s and participating on the cheerleading squad. Upon graduation, she earned a full dance scholarship through her childhood of ballet lessons to the University of Michigan. However, she would go on to leave college at the age of twenty to pursue a career in entertainment in New York City.
When she arrived in Alphabet City with $35 in her pocket, she began studying with the dance troupes of Alvin Ailey, Martha Graham, and Pearl Lang with the goal of becoming a professional dancer. She always had an interest in music, though, and cycled through several musical acts in her young adulthood. She was a backup singer to disco artist Patrick Hernandez, a drummer for the Breakfast Club, and drummer, guitarist, and singer for Emmy and the Emmys. After a demo with the last band didn’t produce the results she wanted, Madonna decided to pursue a solo career.
Madonna networked with DJs throughout the nightclubs of New York in search of an opportunity; soon Mark Kamins at Danceteria (who also freelanced with Island Records as an A&R executive) attempted to loop in Chris Blackwell. Blackwell was nonplussed, so Kamins brokered a meeting with Seymour Stein of Sire Records. Stein signed Madonna to a three single deal with an option for a full album if they did well. “Everybody” came out in October 1982, and did so well that the option was immediately picked up. “Burning Up” followed up in March 1983, after a switch in producers from Kamins to Reggie Lucas. Lucas proved unsuitable for the album after conflict with both Madonna and the label, so Madonna asked John “Jellybean” Benitez (the in-house DJ at nightclub Fun House) to finish production and remix the existing tracks.
Madonna was released in July 1983, taking into its aesthetic everything Madonna had been a part of up to this point: the disco of Hernandez, the post-punk of Stein, the raw punk aggression of Breakfast Club and Emmy, and the stylistic panache that came with New York City’s early-Eighties nightclub scene. It was poppy, danceable, but with an edge that her contemporaries lacked. Madonna was among the first artists to realize the potential of music videos, and her visual appeal was at the forefront of her promotional push. Her fashion design was developed by Maripol, a compatriot of Madonna’s sometimes-romantic-partner, the modern artist Jean-Michel Basquiat. Thanks to the miracle of cable television, the nation soon swarmed with lookalikes who dressed in a combination of Latina street fashion, thrift store discoveries, reimagined Catholic school uniforms, and messy bleached hair, accented by bangles and crucifixes galore. The little girl from Michigan was rapidly becoming an icon.
By April of 1984, Madonna had begun work on her second album. Despite her wishes to be solely in charge of production this time around, Sire and Warner (their parent company) insisted on hiring a veteran producer to guide the relatively inexperienced artist. She selected Chic’s Nile Rodgers, who was coming off of the success of David Bowie’s Let’s Dance, which he produced to great acclaim. Although Rodgers would be expensive, Warner made the investment believing that their expenditure would be rewarded. With his guidance, Like a Virgin became a star-making release, eventually selling more than twenty million copies.
The ensuing Virgin Tour were Madonna’s first large scale performances to a national audience; previously, she had only played New York nightclubs or intimate television appearances. She recruited the Beastie Boys (who were amused at their inclusion, being familiar with her from the NYC club scene), as the Fat Boys were unavailable. Their impact with young audiences was a direct result of the exposure they earned with her. Initially, she was playing mid-sized theatres, but her management quickly expanded the tour in both number of shows and size of venues. After only two weeks, Madonna was playing arenas that could seat twenty thousand concertgoers.
After taking a break to work on the execrable Shanghai Surprise film, Madonna began working on what would become her next album, True Blue. She was finally a full co-producer on this album, working in conjunction with Stephen Bray and her tour’s musical director Patrick Leonard. On the strength of “Live to Tell”, “Papa Don’t Preach”, and the title track, it would go on to sell twenty five million copies.
She took another break to work on the film Who’s That Girl, which also failed both commercially and critically. The one bright spot from her film work was the soundtrack album of the same name, which featured four new Madonna tracks in addition to other Warner artists. The album sold well despite the film’s crash landing. Afterwards, she geared up for a worldwide tour named after the soundtrack. It was on this incredibly lucrative tour that Madonna earned a reputation as a diva, both in terms of crowd appeal and her behavior to those she considered beneath her. Stagehands weren’t allowed to make eye contact or speak unless spoken to, and icy receptions were given to all but the most valued (read: celebrity) visitors.
Her growth as an artist blossomed into her self-image as an Artist, complete with an ego to match. Like a Prayer was produced by the same group, with an assist from Prince here and there. It’s a much broader album than anything else she had recorded. incorporating a wider variety of influences beyond the dance-pop that dominated previous releases. Her imagery became much more provocative, playing further with the idea of blending the sacred (Catholic icons, crucifixes, rosaries) and the profane (short skirts, exposed flesh, explicit language). Her use of religious characters in the video for “Like a Prayer” led directly to being dropped from a lucrative Pepsi sponsorship, although she was able to keep her compensation due to a shrewd business acumen. The album itself sold fifteen million copies, a drop in part due to her controversies.
Not knowing her own limitations once more, Madonna starred in Dick Tracy, releasing another soundtrack album of her own making titled I’m Breathless after her character Breathless Mahoney. She went out of the road afterwards to promote both albums, with the Blond Ambition World Tour proving to be incredibly profitable. At the time, the only act making more in live performances was Michael Jackson, who she had a somewhat friendly rivalry with throughout the rest of his career.
In 1990, Madonna released what is probably her best record in The Immaculate Collection, her first greatest-hits compilation. If you are utterly unfamiliar with Madonna, first of all congratulations on waking up from that coma, and second of all, listen to this one. There are two new tracks on it that demonstrate her further exploration of transgressive topics: “Rescue Me” and “Justify My Love”. Both are definite attempts to inject heretofore unseen levels of sexual imagery into an already erotic milieu, and the results were mixed. Although the songs are good, was she pushing her audience to the point of discomfort?
Her next album Erotica answered that question with a resounding “yes”. It’s her most explicit work, and it showed where the limits were for the record buying public. Madonna released it in conjunction with her book Sex, the first work from her new Maverick Books imprint to accompany her new Maverick Records. Although the book was a profitable release, the album sold a disappointing six million copies. This was due in part to being banned in several countries (including China) and content that earned her a personal rebuke from the Pope. Undeterred, she embarked upon the Girlie Show concert tour, her most elaborate production to date. It earned nearly seventy million dollars, but cost a ridiculous amount to stage and orchestrate. Any show with fifteen hundred costumes and a twenty-four hour stage set-up is perhaps a bit overblown.
Recognizing that the envelope needed to be pulled back on the table somewhat, Madonna worked on the lighter and softer Bedtime Stories for a 1994 release. She worked with a new group of producers, pivoting to a more R&B influenced direction. It sold well (eight million copies), but it became clear that Madonna’s excesses had harmed her ability to sell albums to the degree she was able to do so in the True Blue era. Despite her shortcomings in the area, she pursued another film role, this time the movie version of Andrew Lloyd Webber’s Evita. She lobbied for the role for years, and her efforts paid off. It’s probably her best acting performance, and if that sounds like damning with faint praise, it is. She’s simply not that good an actress; her skills as a singer and as a “celebrity” only partially translate to the screen. The soundtrack is Webber songs, so shouldn’t count for her or against her. (They’d count against her, to be clear.)
1998 saw the release of Ray of Light, a conscious attempt to continue reinventing herself post-Erotica. It was a reflection of her growing fascination with non-western imagery, both East Asian and Middle-Eastern. She had begun meditating and practicing yoga, and the songs reflect that. Her production team shifted to British techno wizard William Orbit, who pointed the album towards a much less organic path than even her early electro-pop albums. Audiences finally accepted her as a grand dame of pop music, selling more than sixteen million copies. She had recovered from her trough and appeared to be heading towards a musical peak once more.
Music in 2000 turns even further towards the danceable music of her youth, just reinvented for new listeners. Orbit is joined by French producer Mirwais Ahmadzai, who incorporated more “world music” tones and textures into her songs. (I hate the term “world music” and all it stands for, but it’s a good shorthand for what’s going on here.) The results were more subdued, selling just eleven million copies since its release.
Ahmadzai would go on to solely produce her 2003 album American Life, continuing the sound established with the previous album. It sold just five million copies, and for good reason. It’s not good, y’all. It’s Madonna with all of the excesses of her peak with none of the goodwill she may have earned through her career. She was forced to make some drastic changes with her next album, and Confessions on a Dance Floor is certainly a drastic change. It’s the first time that her album is programmed like a complete work, rather than just a collection of songs. Critics fell in love once more, although I am not exactly a fan. Ten million purchases can’t be all wrong, can they?
Anyone who thought her next album Hard Candy was good, was wrong, though. The final album on her Warner Brothers contract (after the dissolution of her own Maverick imprint over the past few years), it’s unfocused and needs editing badly. It only sold four million copies, with no killer singles. The tone of the album is mindless dance-pop with no substance to speak of, and typically even in her glossiest moments there’s an intelligence at work. Hard Candy is just kind of dumb.
After signing with Live Nation for touring and Interscope for album releases, she put out MDNA in 2012. It was a fairly transparent ploy to latch onto more modern artists’ success, including Nicki Minaj and M.I.A. Their appeal to listeners didn’t translate, moving just two million copies. Granted, the musical landscape has changed a great deal since her beginnings in the early Eighties, but that’s not a lot of albums sold. 2015’s Rebel Heart is even more of an attempt to achieve symbiosis with current stars, including Diplo, Kanye West, and Avicii. It’s somehow even more of a sprawling mess than before.
The concert tours supporting these less than stellar albums, though, are more reflective of who Madonna had become: glorified greatest hits nostalgia shows, with a taste of “here’s something from my new album” during which the line to the restroom gets interminably long. Speaking of new albums, 2019’s Madame X (her latest) is fine. Nothing more, nothing less. It’s also the least successful album of her career, which I actually do credit the changes in the music industry. (“Why should I buy an album when I can just stream the singles?”). The promotional tour was directly impacted by COVID-19, as was the entire touring musical industry.
That brings us to the present day. Madonna is almost certainly the most important female musical artist of my lifetime, for better or for worse. Her impact is shown in the way musicians are promoted and managed to this day; every inch of skin shown by a young chanteuse or every controversial promo image can be traced back to the way she presented herself as not just an artist, but as an experience. Let’s go through what I believe to be her fifteen best tracks, starting at the bottom and ending up at my favorite Madonna song. These selections are mine and mine alone, so give me all the credit and all the blame. If you like it, let me know in the comments below or via any number of (ever-increasing) social media outlets. They’re all available in my Linktree.
Without any further ado, here’s number fifteen…
15. Crazy for You
“Crazy for You” is more of a landmark for John “Jellybean” Benitez than Madonna. Although he had worked extensively as a producer and remixer before, this was his first opportunity to work on a non-dance-oriented track. With his success here (Madonna’s second number one single), he paved his way to a lasting career. The song is a non-album track, recorded for the soundtrack of Vision Quest. Madonna made a cameo in the film, and leveraged her appearance into a spot on the soundtrack. It came out at the same time as Like a Virgin, and there was a minor scuffle as to whether she would be able to release both this single and the album at the same time. Cooler heads prevailed, as the main goal of making money became obvious.
14. Take a Bow
After the backlash of Erotica, Madonna attempted to pivot to something softer than its hard-edged electronic sound. Inspired by “When Can I See You Again”, she had her people reach out to Kenneth “Babyface” Edmonds, who met with her and decided to try to work out a path towards audience redemption. The result was the album Bedtime Stories and in particular the song “Take a Bow”. This marked the first time that Babyface used real strings instead of synthesized, a component insisted upon by Madonna and her arranger Nellee Hooper. The video, by the way, features designs from Donatella Versace, John Galliano, and a practically newborn Christian Louboutin.
13. Don’t Tell Me
This is the newest song on this list, and the only one from this millennium. (Sorry, not sorry.) I still think of this as her “late period” because time is made up and there’s a part of me that still believes in my heart that it’s 2005. Anyway, I think this is the most successful of Madonna’s flirtations with rootsier music like country or blues, despite her insistence that there’s gold to be mined in that vein. I’m not sure if it’s a conscious imitation of Sheryl Crow or an inadvertent mimicry at work, but there’s a clear comparison to be made. Her brother-in-law Joe Henry wrote the basics of the song as a throwaway when he set up his new studio; he had about thirty minutes to craft something to record. His wife sent it to her sister, and Madonna decided to make it into her own thing.
12. Dress You Up
In retrospect, it’s ironic that “Dress You Up” landed Madonna within the crosshairs of the PMRC (Parents Music Resource Center) that testified before Congress to attempt to censor “explicit” music. Considering her later work, the lyrics to “Dress You Up” are positively puritan in comparison to something like “Justify My Love”. To wit:
Feel the silky touch of my caresses
They will keep you looking so brand new
Let me cover you with velvet kisses
I'll create a look that's made for you
“Velvet kisses” and silky caresses are hardly cause for concern as opposed to anything in the Sex book.
11. Lucky Star
“Lucky Star” was the fourth single from her first album, and marks the birth of her music video supremacy. Thanks to widespread MTV distribution, a nation of young girls became infatuated with her Maripol-curated look: fishnet, ribbons, wild hair, and statement jewelry. Even her trademark half-gloves were almost instantly de rigueur in high school hallways throughout the nation. The credited producer is Reggie Lucas, but the version everyone knows is the work of John “Jellybean” Benitez, whose succes with Madonna led to an extensive production and remixing career of his own.
10. Vogue
Longtime readers may be aware, but recent invitees may not know of my abiding affection for house music of the early Nineties. “Vogue” is well situated among the pantheon of killer house tracks, thanks to the miracle of producer and co-writer Shep Pettibone. His deftness in creating such a memorable track cannot be overstated. The video, though, is what sets the tone. Choreographed by members of the House of Xtravaganza and fully implementing all of the stylistic hallmarks of ball culture, Madonna forever became associated with the dance even though she had nothing to do with its development. You know what? Just go watch Paris is Burning. Go ahead, I’ll wait. Shout out to Willi Ninja.
9. Who’s That Girl
The ill-fated soundtrack album Who’s That Girl is largely forgettable, but the title track is one of the best songs from this era of Madonna. It picks up where “La Isla Bonita” leaves off, pushing into the latin pop genre with more enthusiasm than tact. It’s a brash, bold song, built (as usual with her music) around a funky bassline with sprinkles of auxiliary percussion. Nearly every (good) Madonna song has both of those elements in effect, and “Who’s That Girl” is no different. The movie’s terrible, though. No redeeming that.
8. Holiday
With “Holiday”, Madonna’s chart success truly began. The bubbling up of “Everybody” and “Burning Up” landed her a record deal, but “Holiday” was the first single she released that really moved copies. It was her first top ten in any number of countries, and marked her first appearance on the Billboard singles charts. Initially, the song received airplay on what are now considered “urban” format radio stations, as Sire went out of their way to hide Madonna’s race from potential listeners. After the success of “Holiday”, though, they realized her appearance was a clear selling point.
7. Express Yourself
Although modern audiences may be more familiar with Lady Gaga’s cover of this song, “Express Yourself” is a landmark achievement in Madonna’s career. She was able to fully integrate a video and a song together to make a bold statement about female empowerment and the role of toxic masculinity in tearing down the power of women. The song itself is a strong club stomper, but her visual and especially her Gaultier-designed wardrobe make the lasting impression. Madonna’s image revolves around two poles: the street punk of Like a Virgin and the cone-bra excess of “Express Yourself”.
6. Like a Prayer
The entire Like a Prayer album, but especially the title track, is a declaration that Madonna has transcended the limitations of pop stardom and ascended to the level of an Artist with a capital “A”. Her incorporation of gospel music, in combination with her transgressive lyrics and frankly stunning visual iconography, shows her growth as a musician and as a cultural vanguard. Ostensibly the guitar parts are credited to David Williams and Chester Kamen, but at least some of the track was performed by none other than the purple one himself, Prince. Madonna tried to collaborate more with him for the album, but he had set himself up in Minneapolis, a city that she could not bear to stay in for any length of time.
5. Cherish
“Cherish” is almost a mash-up in and of itself. Combining the pop sensibilities of al of the late Sixties hits like the obvious (The Association’s “Cherish”) and the more obscure (Paul Anka’s “You Are My Destiny”) with modern stylistic conventions like synthesizers and drum machines results in a delightful little package of supreme listenability. Unfortunately, this single from Like a Prayer is one of Madonna’s least favorite songs. She noted a lack of understanding of what makes a song a hit, and used this song’s rather simple lyrics as a touchstone of her bewilderment. (She used much more offensive language in her criticism, but I digress.)
4. Like a Virgin
When you think of Madonna songs, this is probably the first or one of the first songs to come to mind. Initially, producer Nile Rodgers didn’t want to use “Like a Virgin”, thinking that the language would be off-putting to both consumers and radio programmers, and that it would be too provocative to sell. He was persuaded by Madonna herself, who believed in the song and the power of controversy to sell a brand. (That’s a skillset that would serve her well up until about Erotica, where things probably got out of hand.) The title track to her breakthrough album made her an international icon, and the song itself is pretty good.
3. Open Your Heart
Although she usually is dismissive of her skill as a songwriter, Madonna admits that she has a knack for the finishing touch on a track. In the case of “Open Your Heart”, it began as a rockier song to be pitched to Cyndi Lauper by the original writers Gardner Cole and Peter Rafelson. Madonna’s management heard the demo, then asked Madonna to take a swing at refining it to fit her vision for True Blue. She reworked it as a dance song, changing the lyrics to suit an explicitly female protagonist, and added the killer bassline. To her credit, she nearly always starts with a bassline and builds from there. Speaking as an appreciator of the low-end in all ways, this is one of her best.
2. Borderline
When Madonna went to record her debut album, she asked Reggie Lucas to produce instead of either Mark Kamins or Stephen Bray, both of whom had worked on the original demos and singles that earned her her deal. When she began working in earnest, she didn’t have enough original material to fill the album. Lucas contributed two songs, “Physical Attraction” and “Borderline”, to supplement the Madonna-penned tracks. However, Lucas’ vision was far more busy and complex than the relatively simple and sparse arrangements that Madonna preferred, leading Lucas to leave before the final mixes were done. The resulting thrown-together mix for “Borderline” is a hybrid of the two styles, and somehow it’s absolute magic. It would be her best track if it wasn’t for…
1. Into the Groove
Madonna’s best song was one that shouldn’t have been released. After being cast in Desperately Seeking Susan, she was asked if she had a song that was suitable to use in the background of one of her scenes. She suggested a demo that she and Stephen Bray had recorded (on Mark Kamins’ dime) for potential use for Cheyne, Kamins’ protege. Kamins was upset, leading to the end of their working relationship. Because the song was introduced to both the movie and the Like a Virgin too late for inclusion on the official US releases, it was put out as a B-side to “Angel” instead. It was released in the UK, though, where it became Madonna’s best-selling single of all time. It’s on numerous compilations, and it’s a hallmark of mid-Eighties dance music. She reached her peak with this one.
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