While no one wants to hear this (least of all ageists or the Beyhive), Madonna remains, despite Billboard’s recent list to the contrary, the greatest pop star of the twenty-first century. A statement that, of course, could be deemed as “fighting words.” Oh sure, many would agree that such a claim could easily be made about M if one were talking about greatest twentieth century pop stars, but the truth is that many more would contest giving such a title to Madonna even in that century. The one she inarguably molded and shaped (the back half of it anyway) in a manner so indelible that it set the tone for the next one. Such detractors would instead try to insist that it was one of her other rivals in the “1958 trinity”—Michael Jackson or Prince—who warrant “the greatest” title for the twentieth century. Hell, even those who would rather give the title to Janet Jackson (*cough cough* Lizzo—though one wouldn’t take her opinion too seriously these days).
In short, anything to avert giving Madonna her credit where credit is due. And that includes the twenty-first century just as much as it does the twentieth. But the thing about being a pop star—especially a female pop star—is that you’re automatically discounted from such accolades once you’ve “been around the block” enough times. And Beyoncé, at forty-three, and Taylor Swift, at thirty-five, are still “young-but-old-enough” to fit neatly into the box of this Billboard categorization (coming in at number one and number two, respectively). That Madonna wouldn’t even be taken into consideration for this list is telling of two larger issues: 1) obviously, ageism and 2) the idea that just because a musician is “of a certain age,” they can no longer be capable of making an impact on “the culture.” Indeed, such a thought is inconceivable to most people. And yet, that is precisely what Madonna has done in her “later career”—the one that’s unfolded for, as of 2024, slightly longer in the twenty-first century than in the twentieth. As a matter of fact, she’s released an equal amount of studio albums in both centuries—seven and seven. With the announcement of another album (produced, again, by Stuart Price), she’ll soon have eight in this century. Which means, objectively, she’s been more prolific in her “later years.”
To that end, it was with 2019’s Madame X (Madonna has now been on the longest album “hiatus” of her career since the release of said record) that Ms. Ciccone continued to prove why she remains worthy of “the greatest” title. As some of her most daring work to date, Madonna, as one of the few/only pop stars to have this much longevity in her career, reminded that the best way to stick around for this long (a feat that M once quipped is the most controversial thing she’s ever done) is by being unafraid to experiment and explore. To test your own artistic boundaries, in addition to the “expectation” boundaries of listeners. This is also, in part, why Madonna wasn’t even a thought on the Billboard list. Because to deviate from the norm is to, inevitably, risk losing popularity.
Pop, as many often forget, is short for “popular” (incidentally, the title of Madonna’s first original/non-repurposed single of the 2020s, marking her as one of the only musicians to have a single enter the Billboard Hot 100 over the course of five consecutive decades). And yet, the genre has come to mean something else entirely to most listeners. For it has a still immediate connotation of being associated with people like Harry Styles and Shawn Mendes on the male front and people like Taylor Swift and Sabrina Carpenter on the female front. In other words, “pop star” is a phrase that has an extremely white overtone. Which is yet another reason why, whether pop enthusiasts wanted to admit it or not, there was so much “outrage” about Beyoncé snagging the top spot on the list. Because, yes, it’s true that artists like Beyoncé and the embarrassment she’s married to, Jay-Z, are not associated with that genre of music at all. Which is why, along with Rihanna, Usher, Bad Bunny, Lil Wayne, Kanye “Ye” West and others who made the top twenty-five on the list, it seems somewhat unexpected. What with Billboard itself being the entity to long separate “pop” music from rap, hip hop and R&B. The elephant in the room being that the category of “pop star” has typically been one reserved for whites. But that’s not what makes Beyoncé’s ascent to the top of the list so “controversial” (particularly to Swifties who were subsequently called out for racism because of their tantrum over Taylor not securing the number one position). It’s that, like Swift, when compared to Madonna, her constant mainstream presence in the lives of the masses was not as key to the way that pop culture continued to be formed and manipulated by one of its postmodern progenitors.
Naturally, one will try to argue: how can you say Madonna’s presence was more felt in the mainstream in the twenty-first century? She wasn’t mentioned half as much as Beyoncé or Taylor. Well, what one means by “felt” is that the things she did to promote her work (as well as the work itself) still continued to set the bar for others—your beloved Beyoncé and Taylor included. And not just that, but the music she released altered the course of twenty-first century sound from the very beginning of it, starting with 2000’s Music. Like Madame X, it was an album that dared to say, “I have nothing left to prove and I don’t give a fuck about mainstream approval.” And this came at a time when it was also key for Madonna to remind the masses why she offered something different than the cookie cutter pop sounds being doled out by the next generation of princesses: Britney Spears and Christina Aguilera (the former made number six on the list, while the latter was relegated to the “Honorable Mention” section). Something altogether her own sound. And with that unique sound was the unique image to go with it. In 2000, that image was ghetto-fabulous/glam cowgirl. An image that, needless to say, Beyoncé would repurpose in 2024 for Cowboy Carter.
But reinventing the sound of music through Music wasn’t the only avant-garde thing she did in 2000. Madonna was also among the first pop stars to truly maximize the internet’s potential in terms of her reach by livestreaming a promotional concert from the Brixton Academy in London on November 28, 2000. As MSN’s then marketing manager, Tracy Blacher, put it, “No one has ever attempted anything on this scale before. We gave people the chance to see and hear Madonna’s fantastic return to the stage and witness the first online live performance for free.” In short, Madonna, as usual, was one of the only pop stars to be ahead of the curve on wielding new technology to her advantage. This occurred again in 2005, when she promoted her lead single from Confessions on a Dance Floor, “Hung Up,” by way of a Motorola commercial.
Leaning into the then new phenomenon of listening to music on your phone via iTunes, Madonna was joined by other musicians, including Iggy Pop, Alanis Morissette and Little Richard, cramming themselves into a phone booth. The premise all designed to accent that, for the first time, your phone could contain all the music you wanted to listen to, courtesy of the iTunes “media player.” In fact, this edition of the Motorola phone was the first to integrate iTunes before the iPhone itself, released in 2007 (the first version of it, anyway). All of which is to say that, long before anyone knew the power that the internet and smartphones would hold over music listeners, Madonna was embracing rather than resisting the change. Using it to her advantage as she always did when it came to media and technology (this would later extend to mediums like Snapchat and NFTs).
And she would have a lot of damage control to do while using that skill to her advantage in 2005, which also marked the year that Madonna fell off the horse she was riding in honor of her birthday (August 16th), celebrating it at Ashcombe House, the estate where she lived with her husband at the time, Guy Ritchie. Considering that the ageist remarks against her were already rampant, Madonna didn’t need fuel added to the fire with regard to the perception that she was some “feeble” “old” woman. So yes, after breaking three ribs, her collarbone and her hand, Madonna was metaphorically back in the saddle soon after, filming the video for “Hung Up” in the fall, which was choreo-intensive, to say the least.
It set the precedent for Madonna’s swift recovery after suffering from a bacterial infection in the summer of 2023—one that almost caused her to die. Mere months later, she was embarking on the rigorous world tour she had been rehearsing for when the bacterial infection happened. Some speculated that the infection was caused by her overworking perfectionism, which weakened her immune system. Others were likelier to point at the fact that bacterial infections can also be caused by surgical procedures. And it’s no secret at this point that Madonna is fond of those. When she woke up in the hospital, as Madonna tells it, she was surrounded by her children. The “accomplishments” she continues to say she’s most proud of. Which brings one to another indelible way that Madonna affected pop stardom in the twenty-first century: she officially made it “okay” to be a mother while still being a badass sexy pop star.
Before Madonna, no one else had done that (something that her recent biographer, Mary Gabriel, calls out in Madonna: A Rebel Life). Madonna was there—continuing to be the rebellious, controversial woman she had always been after having kids—long before Britney Spears or Beyoncé had their children and suddenly seemed to make everything solely about motherhood (you would never catch Madonna cheesily clutching her baby bump). And the difference between Madonna and them is, not only did she fortify a strong relationship with her children despite her media frenzied existence, but she never kept them shrouded in secrecy (that’s Beyoncé’s thing). Spears probably would have if she had been given more of a choice in the matter, but she had the unfortunate luck of being at the peak of her fame at a time when the paparazzi could do just about whatever they wanted, totally unchecked.
In 2012, the year that Madonna got mentioned on Billboard’s Pop Star of the Year list for being the “Comeback of the Year,” she performed at the Super Bowl. A year before Beyoncé would do the same. Just another prime example of Madonna always being the one to do it first, to blaze a trail and to remind audiences that, out of everyone, she’s the person who knows how to put on a fucking show. Knows that it’s all about spectacle, while cleverly hiding one’s “political agenda” within that spectacle.
She persisted in doing so less subtly for that year’s MDNA Tour, which would not only find her at the center of several controversies (some involving Pussy Riot and Marine Le Pen, to name a few), but also become the highest-grossing tour of 2012. Just as the Re-Invention Tour was the highest-grossing of 2004 and the Sticky & Sweet Tour was the highest-grossing of 2008. Madonna continued to set touring records as recently as this year, becoming the first artist to put on a show of The Celebration Tour that would become the most attended free concert of all-time (attracting 1.6 million people to Copacabana in Rio de Janeiro).
The various ways in which Madonna has shaped the industry in the twenty-first century also often included, as usual, taking a bullet for those who came after her. Case in point, the leak of her 2015 album, Rebel Heart. While leaks had been known to happen before, it was never quite on this scale. The type of scale that would prompt Madonna to bump up her album release date by roughly six months. Originally intended for a late spring 2015 release, Madonna chose to make Rebel Heart available for pre-order in December of 2014, which automatically downloaded six of the tracks from the album. Eventually traced to an Israeli named Adi Lederman, it was also revealed that he was the culprit behind leaking a demo of “Give Me All Your Luvin’” in 2012. And while, sure, Madonna had been well aware of the potential for leaks that came with the twenty-first century, in the past, it seemed she had been more capable of getting ahead of them. For instance, “fake leaking” American Life so that when, in 2003, someone tried to download the song or album on a file-sharing website like Kazaa, they would be met with a cheeky Madonna asking, “What the fuck do you think you’re doing? Tried to sneak past me now, didn’t ya?”
As a matter of fact, it is Madonna’s wry sense of humor that has been part of the problem with her “translating” into the twenty-first century as it goes on. With the increasing literalness of everything, it’s apparently a challenge for people to understand when someone is being ironic. In short, when they’re doing something tongue-in-cheekly—which is what Madonna has always done. This includes a video like “Music,” directed by Jonas Åkerlund, wherein she embodies the role of a ghetto-fabulous man—as a woman. Complete with going to strip clubs and pouring champagne in limos…the license plate of which reads, “Muff Daddy”—because it was still a time when Puff Daddy could be referenced without scandal. On that note, Billboard’s Pop Star of the Year title went to Puff Daddy in 1997, a “wilderness year” for Madonna that fell in between Evita and Ray of Light. In the interim, she simply collected awards for the former. Yet despite her omnipresence in the 90s as well, Madonna never managed to get Pop Star of the Year after the 1980s, garnering the honor in 1985 and 1989 (while getting “Rookie of the Year” in 1984, arguably one of her biggest moments that would also warrant receiving the title, but it was given to Prince). They couldn’t even be bothered to give the award to M in 1990, when “Vogue” and the Blond Ambition Tour made her more pervasive than ever. Instead, Janet was the victor that year.
In point of fact (and much to Lady Gaga’s chagrin), Madonna, Janet, Beyoncé and Rihanna are the only pop stars to have been named Pop Star of the Year more than once (Madonna, as mentioned, in ’85 and ’89, Janet in ’90 and ’93, Beyoncé in ‘03 and ‘14 and Rihanna in ’07 and ’12—the latter year being when Madonna was given “Comeback of the Year” for her Super Bowl performance and MDNA topping the Billboard 200). One might note that Madonna is the only white woman on that list. Which feels pointed considering she’s often freely stated that she has always identified more with the Black (and gay) community.
Oddly, Britney Spears—who made number six on Billboard’s list of Greatest Pop Stars of the Twenty-First Century—was given the title just once, in 1999—back in the twentieth century. During some of her biggest twenty-first century years, 2000, 2001, 2003 and 2007, the title instead went to *NSYNC (the injustice!), Jennifer Lopez, Beyoncé and Rihanna, respectively. Just further fanning the flame of the theory that Billboard might not necessarily know what the fuck it’s talking about sometimes. Which is why, even though Madonna is the only “elder” female pop star who has put out a consistent breadth of impactful work in this century (unlike, say, Cher or Janet Jackson), it has meant, apparently, nothing to them.
And, on that note, Billboard made the claim, “…these Greatest Pop Stars are NOT mathematically determined by stats like chart position, streams or sales numbers. Those play a big part in our final rankings, of course—you can’t be one of the greatest pop stars of the century without great pop hits and great pop albums—but so do things like music videos, live performances and social media presence, and more intangible factors like cultural importance, industry influence and overall omnipresence.” But what they didn’t bother to say was that women of “a certain age,” no matter how culturally relevant they continue to be, will never be considered for such a list.
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