“I was like the Madonna and the Michael Jackson of my day,” Tony Bennett once told Conan O’Brien during a 1993 interview. The notable distinction between Madonna and Michael being that the former constantly changes her image. Jackson, like Tony, did not bother to do anything significant in that arena. In fact, he leaned into his image (awash with sequins, fedoras and exposed socks) all the more as the years went by: the very thing that can (and usually does) turn one into a caricature. The same went for Bennett, who stalwartly refused to update his look (a black tuxedo and bowtie) as the decades passed. Not even after he first “resurged” onto the scene in a big way at the beginning of the 90s. For Bennett had already capitulated to rebranding once before, at the height of the psychedelic rock craze. Or rather, just after it—releasing Tony Sings the Great Hits of Today! in 1970, complete with psychedelic cover art.
The so-called image change and attempt to do something different was immediately lambasted, and Bennett was soon after dropped from Columbia Records. An interesting reaction, when considering that most women who refuse to change their look or sound over time end up being cast aside and relegated to whatever time period they rose to prominence in (e.g. Nancy Sinatra with the 60s, Stevie Nicks with the 70s, Cyndi Lauper with the 80s, Alanis Morissette with the 90s, Britney Spears with the 00s, and so on and so forth).
Mariah Carey, too, spoke of Columbia Records trying to “button her up with the 90s” by capping off the decade with a greatest hits album of hers. Carey wasn’t having it, and released 1999’s Rainbow the year after #1s came out. With “Heartbreaker” as the lead single, it served as a complete sonic shift into her artful melding of pop and hip hop, which she had already hinted at plenty with 1997’s Butterfly. An album, incidentally, she had to fight tooth and nail to secure some creative control over, made perhaps easier (or harder, depending on who you ask) as a result of being in the process of cutting ties romantically with Tommy Mottola, then CEO of Sony Music (a.k.a. her boss).
Carey has reinvented herself to a lesser extent than Madonna since the dawn of the 2000s, with the latter unveiling new “personae” as readily as a new outfit, ramping up what some critics would call her “shtick” with more intensity than ever at the beginning of the twenty-first century. Starting with Music in 2000, Madonna continued to reinvent herself tirelessly, with the glam cowgirl aesthetic giving way to a Che Guevara-inspired war rebel guise for 2003’s American Life. She then continued with a 70s-chic dancing queen image for 2005’s Confessions on a Dance Floor, a sexy boxer for 2008’s Hard Candy, a molly fan on 2012’s MDNA and a romantic freedom fighter on 2015’s Rebel Heart.
By the time 2019’s Madame X arrived, Madonna decided to roll all of her many personae into one with the marketing speech, “Madame X is a secret agent traveling around the world, changing identities, fighting for freedom, bringing light to dark places. Madame X is a dancer, a professor, a head of state, a housekeeper, an equestrian, a prisoner, a student, a mother, a child, a teacher, a nun, a singer, a saint, a whore…a spy in the house of love.” That last phrase being a clear nod to the Anaïs Nin book of the same name. For Madonna is nothing if not a bridge between high and so-called low art. All while also showing that to stay “relevant” in the music business as a woman, you have to be willing to shed previous images as willingly as snakes shed their skin in order to survive. Madonna being among one of the few women musicians to do that, therefore have a chance at competing with Bennett’s far more effortless longevity. And yes, even Lady Gaga (the best Madonna impersonator currently working today), Bennett’s “bestie” in recent years, is another example of a woman who has to reinvent. Even aesthetically static Taylor Swift (who can always be counted on for the same blonde hair and red lipstick) has chosen to perform this year under the banner of the Eras Tour…overtly wanting to highlight the notion that she’s reinvented herself repeatedly over her now decade-plus career.
Then, of course, there’s Cher, who occasionally gets held up as an example of a woman who has “lasted” for decades, though she isn’t actually putting out any new material or bothering to tour anymore. Madonna stands alone in that category (even if her recent bacterial infection might have put a delay on her forthcoming Celebration Tour). And it’s precisely because she’s among the few to have put in the ceaseless work to remain in the spotlight that’s “required” only of a woman. This then getting branded as “desperate” or “gimmicky” as critics insist she essentially ought to put herself out to pasture…as she once phrased it during a 1992 interview with Jonathan Ross. And it was also in that interview that she herself called out Jackson’s total inability to reinvent himself now and again, telling Ross, “I really wanted him to cut his hair. Sometimes I think it’s good to cut your hair and start all over again.” She then added, “I wanted him to get rid of those loafers and the white socks. I just thought, you know, just try something new.” Clearly, there’s a reason their “friendship” didn’t last too much longer after attending the 1991 Oscars ceremony together. For no man likes to be reminded that his “look,” therefore his entire self, is “outmoded.”
Male musicians, instead, appear to prefer coasting on the laurels of what secured them their fame and accolades when they were younger, never needing to try anything else different afterward because society simply does not place that onus upon them. Nor does society judge men for continuing to pursue their art well past “middle age.” In point of fact, Bennett, like Madonna, referred to artists such as Picasso when he said, “Right up to the day they died, they were performing. If you are creative, you get busier as you get older.” Few people have been as willing to “grant” that to Madonna, who has also vowed to never stop (hear: “Like It Or Not,” with its lyrics, “You can love me or leave me/‘Cause I’m never gonna stop”). And yes, in 2015, she name-checked Picasso as well, stating, “I like to compare myself to other kinds of artists like Picasso. He kept painting and painting until the day he died. Why? Because I guess he felt inspired to do so. Life inspired him, so he had to keep expressing himself, and that’s how I feel.”
Of course, when Bennett said it, it was fine. When Madonna said it, it was self-aggrandizing. Proof that she was conceited enough to hold herself in such high regard as a “master” like Picasso. Well, where’s the lie? Madonna is an undisputed master of pop music. And even Bennett conceded to that in 1996, when he presented her with an Artist Achievement Award at the Billboard Music Awards. To introduce her, he confirmed what most already knew: “She has consistently surprised and delighted us with her fascinating transformations, with a dazzling display of invention. She’s kept us on the edge of our seat—wait till you see what’s next.”
With Bennett and musicians like him, there’s never any such excitement or anticipation. Rather than consistently reinventing, they merely stay consistent. Nonetheless, their reverence goes unquestioned. And while Madonna is a master in pop music, Bennett, in contrast, was a master in “crooning,” specifically “American standards” (all well and good, but not exactly leaving much room for “originality”). This included covering work from Rat Pack staples like Sammy Davis Jr. And whenever Bennett sang the latter’s “I’ve Gotta Be Me,” it proved a telling anthem for a man who never had to compromise the way he looked or sounded (save for that one time in 1970 that put him off even the mere idea of experimentation forever).
Not solely because of his vocal talent that didn’t need any additional “bells and whistles,” but because he had the luxury of being a male performer. A fact that meant alterations to appearance (and sound) were hardly “requisite” the way they tacitly are for women who want to enjoy the same longevity in the music industry. Which is perhaps why Madonna remains a rare example, with even Janet Jackson disappearing more than once or twice into the abyss and Kylie Minogue only happening to touch on the virality phenomenon with “Padam Padam.” But that, too, is a direct result of Madonna’s boundary-breaking for women in Minogue’s age bracket. Boundaries that, for men, do not exist at all.
