“Retrospective: How Millennium Music Taught Me the Pleasure of Swagger” by Simona Supekar

Issue 24 / Winter 2021 / Special Issue: Pleasure

The lyric went like this: “If six of y’all went out, then four of you were really cheap. ‘Cause only two of you had dinner. I found your credit card receipt.” The blend of simple arithmetic and deductive reasoning from the intro of Whitney Houston’s 1999 “It’s Not Right, But It’s Okay” gave listeners entrée into a song that captivated so many like me coming of age and anxious about the millennium.

When the original song dropped, I was a junior at a college in Ohio, far away from my home in the suburbs of Washington, D.C. My social circle was mostly brown, Black, and queer. We struggled with the dichotomy of attending an expensive liberal arts school while feeling marginalized at one. We missed our families and our families traumatized us. We were all either in terrible relationships or were pining to be in what would become one. We were in awe of the new vocabulary education had given us to see the world and ourselves, for the first time. We’d never see things in isolation again, but as parts of systems. And the systems horrified us. Songs like this—belted out from deep with the aid of soul and liquid courage—gave us confidence to deal with the growing stockpile of ruinous experiences for which we now had a new framework to understand.

From a critical race perspective, “It’s Not Right, But It’s Okay” contextualized the idea of self-respect and the joy it brought by presenting a woman of color reclaiming it as a function of her own interests rather as something that suited white audiences. It addressed more incisively the gaps in my emotional intelligence essays like Joan Didion’s “On Self-Respect” could not quite fill. As an Asian American and more specifically an Indian American, it was also formative to my eschewing of respectability politics and the idea of a model minority. Because of the dearth of South Asians in pop culture, many of my values were gleaned from watching Black and Latina artists, thus shaping some of my earliest notions about racial inequity. At its most basic level, the song taught me the nuance between the different levels of pain I would encounter in my life: things like breakups, for instance, would be nearly unbearable. But they would not break me. At a more theoretical level, the song reinforced for me the perils of obsequiousness. It exemplified the notion that as an Asian American, unless, as scholar Curtis Chang argues, I “challenge racial misconceptions and inequalities” I “will be nothing more than a…coolie” (373).[1]

My earliest memories of Whitney were of as a child jumping up and down until I passed out to the “I Wanna Dance With Somebody” music video with my cousins during summer visits to Ohio. Ohio was the Promised Land: my cousins had chocolate milk, chocolate chips for their cereal, soda, and most importantly, MTV. My whole family loved Whitney. Her vibrant, wholesome, and undeniable talent coupled with white-sanctioned success provided the alchemy that could on its surface repel anti-Blackness even within my own community. She was, I imagine many first-generation Indians thinking, the American we could all strive to be.

But “It’s Not Right, But It’s Okay” was not the Whitney sound from my youth. Echoing my own reckoning with patriarchy and capitalism, the song—specifically the Thunderpuss remix released in 2000 as I graduated—electrified me with agency I did not know existed. In the video, her unflinching stare—the focal point, really—greets the summoned viewer from above a mirrored table. Set against an onyx background, she is wearing a choker to match a skintight dark greenish-black leather dress embellished with a chain and cape. Confidence has replaced her early-career buoyancy and a series of apt hand gestures narrates her pain: pointing, door-slamming, “come at me,” “shoo,” and my personal favorite the exasperated “GTFO of here” after she sings, “So why did 213 come up on your caller ID?” Whitney doesn’t want to dance with anybody here. She is mostly still and in fact her eyes, hands, mouth, and stance do most of the work. A woman of color calling the shots. Swagger in action.

Like Whitney’s, my image at the time also changed, albeit in much more low-stakes kind of way. Until then, I dressed the part of the hippie activist I had wanted to be and to some small extent, was. I began my activist trajectory at fifteen with Amnesty International and until that point had a keen awareness of global political issues yet little of my own privilege and role in them. In 1999, Keri Russell made waves for cutting her signature long hair off in Felicity, and I had done the same the year before when I was twenty. I also ditched my tie-dye and bell bottoms for better-fitting, minimalist clothes. Yet the more profound change was not in my appearance, but in my attitude. I was raised within a middle-class Indian community that introduced people by the degrees and jobs they had and had not entirely disabused itself of the concept of caste. I began to recognize and reject these medallions of the model minority and the racism that casteism relies upon and regarded achievement as something to be sought through humanistic concerns, not capitalistic or white supremacist ones.

I dropped my aspirations to become a psychiatrist and decided to major in English and Anthropology, not thinking much about what the future held but knowing that I wanted to work in social justice. I worked various jobs in my local college community to support myself, including night shifts at a runaway shelter doing intakes and counseling troubled youth and at the nearby food pantry. My political consciousness shifted from global to local with a particular urgency. I became involved in the South Asian organization on campus and occasionally allied myself with other Asian American causes, such as the fight to retain Asian American faculty. Sometimes I was ardent and impassioned, and other times I was overwhelmed and half-committed. Eventually, I began dating a fellow classmate who was also Asian American, and I thought I had finally found a person who understood the entirety of me. After I graduated, we moved together to Los Angeles where I’d accepted a high school English teaching job.




If six of y’all went out, then four of you were really cheap. ‘Cause only two of you had dinner. I found your credit card receipt




There were red flags all along, but I clung desperately to the idea of a certain type of love rooted largely in cishet patriarchal ideals. I had no models for what interracial love between two brown people from different cultures could look like, and I did not even know if that mattered. What I found was that brown love did not necessarily guarantee better love. We broke up in early 2005 and he moved out of our apartment when our relationship became destructive. Nearly ten years later, I found out inadvertently from a mutual friend that he had in fact cheated.




All this time I thought I had somebody down for Whitney.

It turns out, you were making a fool out of me.




The glorious melisma in this lyric juxtaposed against the absurd premise that one could make a fool of that sound’s creator was a symbolic lesson in self-worth. She’s making a fool out of you, sucka, it said. I listened.

It’s no surprise that this song and other contemporaneous ones like it helped build my backbone. Coming off a grunge era that only partially spoke to my kind of angst, it was primarily the voices of women that resonated with me during that strange time from the late nineties through the early aughts. After a decade of music where bands like Nirvana, Stone Temple Pilots, Pearl Jam, Soundgarden, Alice in Chains, Foo Fighters, and others defined the zeitgeist through white masculinity, music from Black and brown women of the late nineties argued for the rapture of self-worth.

Consider the lyrics from popular grunge and alt rock songs around that time:

“A mulatto, an albino, a mosquito, my libido…” —Nirvana

“You ride the waves and don’t ask where they go/You swim like lions through the crest/And bathe yourself in zebra flesh…” —Primitive Radio Gods

“Living under house/Guess I’m living/I’m a mouse/All’s I gots is time/Got no meaning just a rhyme…” —Stone Temple Pilots

“Doo doo doo doo dingle zing a dong bone/Ba-di ba-da ba-zumba crunga cong gone bad…” —Red Hot Chili Peppers

And let’s not forget: “Chickity China/The Chinese Chicken” from the Barenaked Ladies.

Nevertheless, I too was riveted by this music because it combined expert musicianship with a powerful rendering of a collective mood—a blend of apathetic and self-destructive. Nineties grunge and alt rock bands indeed made a convincing case for why words didn’t matter, but the burgeoning music from women artists of the late nineties proved that they did.

A tide was turning in the way female pop musicians around Y2K were communicating. The contrast between Whitney’s “The Greatest Love of All” and “It’s Not Right But It’s Okay” or Toni Braxton’s “You Mean the World To Me” and “He Wasn’t Man Enough For Me” echoed my own chasms in maturity. Musicians of color who’d been sold to me during my childhood as uncritical, heart-on-sleeve romantics appeared more empowered and were singing in ways that mirrored my Gen X disgruntlement. Perhaps the prevailing apocalyptic narratives had a role. Or their clout had given them more agency to challenge the industry. Or perhaps the artists were just growing up, like I was. Houston confirms the latter when she talks about the new direction of songs like “It’s Not Right But It’s Okay,” stating in a 1998 interview with Billboard, “I wasn’t into the syrupy kind of vibe…I just didn’t feel like singing about ‘I Will Always Love You.’ I’m a working mother, I’m a wife, I’m an artist…and it’s not always like, ‘Everything is beautiful in its own way’”(Newman).

Critics have written about how the Riot Grrls, The Spice Girls, Courtney Love, Britney Spears, and others were shifting the conversation toward general female empowerment, but I needed the more specific barbs that only Black and brown musicians could supply. They not only rejected the male gaze but evoked what I craved—swagger.




Close the door behind you, leave your key.

I’d rather be alone than unhappy.




After my breakup, I spent a year in therapy, read critical books about relationships like bell hooks’ All About Love, and left my teaching job to do more writing. I created marketing copy for a stock photo company while freelancing at night, writing music reviews, design horoscopes, and just about anything I could until I had enough of a portfolio that eventually propelled me into a job I loved as a fashion writer and editor. When I could think about something other than paying back student loans, I reconnected with friends and embraced sisterhood fervently. I reacted to an Islamophobic post-9/11 world and became even more politically aware, protesting the U.S. involvement in Afghanistan and Iraq while living according to my values. I was swagger-adjacent.

Throughout everything, the song followed me. Five years after its release, it would carry me through my breakup. Ten years after, it pushed me through some mile of a half-marathon. Twelve years after, it would be on my bachelorette party playlist reverberating throughout a Las Vegas hotel room before I married my husband. Thirteen years after, Whitney’s death. Twenty years later—I still cannot stop thinking about the song.

“It’s Not Right, But It’s Okay” was more than an anthem for Gen-Xers of color; it was an indictment on the way that patriarchy plays us. Similar work by Black and Latina musicians at the time such as that of Mariah Carey, Toni Braxton, Jennifer Lopez, Blu Cantrell, Lil’ Kim, Aaliyah, Missy Elliott, 702, TLC, and Destiny’s Child all made me feel visible. This music transformed me from a passive music consumer into an active one.

In 2016, Beyoncé asked whether it was better to look jealous or crazy; the music of the early millennium laid the foundation for that question to be asked. Weaving in themes of love, betrayal, resilience, revenge, and solidarity, the artists explored their quotidian realities, a bold vision of personal triumph the foregone conclusion throughout all. As Ann Powers, NPR Music Critic writes, “The unrest on the rock scene in the first half of the 1990s felt to many like a paradigm shift…into this fractured landscape came a diverse array of artists who took on the challenge of expressing self-aware womanhood in very different ways.”

During a time rife with chaos: the Columbine shooting, Y2K, the continued struggle for gay rights, the disappointment of the 2000 election, and 9/11, the music pulsed through me and through it, I could love, covet, and destroy.

Often, the critics did not agree with me. Take, for example, J.Lo’s 1999 debut single “If You Had My Love,” a Darkchild-produced hit like “It’s Not Right, But It’s Okay” and Toni Braxton’s “He Wasn’t Man Enough.” Though it stayed #1 on Billboard for five weeks, some reviews critiqued the song as derivative, with an L.A. Times writer claiming that it sounded “like a Brandy or Monica reject. (She is Paula Abdul 2000.)”

But what I saw was a brown woman subverting norms by dictating the terms of her love. “If I give you me/this is how it’s got to be/first of all, I won’t take you cheating on me” was a bold directive to women, but especially women of color who’d been taught by society to settle for any fool with a mouth. Her music video underscores this subversion. As Lisa Nakamura writes in her book Digitizing Race, “Shots of Lopez tracked by surveillance cameras alternate with her image as represented in a Web site: she shares the stage and gaze with the new media design interfaces in which she is embedded in an extremely overt way. This puts a new spin on the traditional female position as object of the gaze.” Lopez (through the eyes of a young Adam Rodriguez), throws the voyeur’s voyeurism back as prescient commentary on the rise of the internet era. In college, J.Lo validated our big hair, our prioritizing of dance, our trips to lusterless Ohio malls to find cute tube tops at Rainbow. She would not let us succumb to mediocrity.

Throughout my twenties, I realized my professional successes were inversely proportional to the time I spent around men. Before I was thirty, I had won awards for my copywriting and was managing a team of freelancers shortly before going to graduate school. I began to learn the value of the company I kept and thrived when there were no busters around to diminish me.

Who deserves to be in our lives? Mariah Carey’s 1999 “Heartbreaker” reminds me of the answer. The video chronicles a miraculously fly Mariah and her BFFs confronting her rumored-to-be-cheating boyfriend at a movie theater. You think it’s going to be Jay-Z since he’s on the track but…it’s Jerry O’Connell from My Secret Identity in a raggedy UCLA t-shirt? It’s no wonder she chose to fight a version of herself at the end. The 2001 film Glitter was also pivotal in the conversation about the mental health of women of color because it released during a time when Carey was publicly battling mental health issues. Though described as a “Monumentally ill-conceived…butt-numbing exercise in tedium, sporadically redeemed by moments of unintentional hilarity” (TV Guide), it persists as a reminder of why Black and brown women should prioritize self-care.

Part of what emerged for me as swagger throughout this time is the ability to hold sisterhood close despite all the forces working against it. When it came to infidelity, for instance, there were few pop culture counternarratives that pushed back against hating the “other woman.” On its face, Toni Braxton’s “He Wasn’t Man Enough” (2000) might appear to reinforce tropes about catfights. But by Braxton’s repeated use of the word “girlfriend,” it is clear the song is a friendly warning to another woman about the perils of being with a cheater. She declares, “Listen, girl/Didn’t he tell you the truth?/If not then why don’t you ask him?/Then maybe you can be more into him/Instead of worryin’ about me.” At the end of the video, “other woman” Robin Givens finally leaves the guy; the epiphany is punctuated by a high-five of solidarity between Givens and Braxton.

Blu Cantrell’s “Hit ‘Em Up Style (Oops)” (2001) created a space to be unabashedly petty for the right reasons, as though taking a moral high ground is almost insincere. The song is like a musical limning of the scene in Waiting to Exhale where Bernie (played by Angela Bassett) blows up her cheating husband’s car. Like director Forest Whitaker, Cantrell allows us to live vicariously through a narrative of satisfying capitalist payback. Is revenge better than money? Is it mature to go on a shopping spree with your cheating man’s credit card? Cantrell blesses us with this earworm to feel okay about screaming Yes!

While some rockers put nonsense into a song purposefully, turning it into a hit despite it, in 2002, Missy Elliott put nonsense into a song accidentally, turning it into a hit because of it. Her genius “Work It” taught me the joy that hustling brings as I struggled to pay bills as a high school English teacher. “Ti esrever dna ti pilf, nwod gniht ym tup” had eked into the vernacular, and a common task of the day was to try and accurately sing along. Over fifteen years later, Elliott revealed that the lyric was the result of an engineering mix-up that she decided to incorporate. Additionally, Elliott teaches body positivity as she “further reclaims sexuality and eros as healing power for all Black women, regardless of size” (Keyes). Elliott extols the virtues of sexual agency by directing her lover to “go downtown and eat it like a vulture” (see also: Lil’ Kim’s life-changing 2000 hit “How Many Licks?”). But it’s always been the very first line that has governed my decision-making most: “Is it worth it?”

The film Romeo Must Die rocked my world in 2000. Starring Aaliyah and Jet Li, it was the first film I’d seen since Mississippi Masala to feature a romantic relationship between an Asian and an African American. Aaliyah’s addicting refrain in “Try Again” from the soundtrack was à propos for my friends and I trying at relationships, jobs, and friendship while sometimes failing miserably. Critics derided the movie when it came out, saying things like “They have so little chemistry together you’d think they’re putting out a fire instead of shooting off sparks.” Yet it has been my life’s mission to enter or exit a room with a fraction of Aaliyah’s cane swagger from the end of the video. Miss-Teeq’s “Scandalous” (2003) achieves a comparable vibe and accompanies another cultural milestone—Halle Berry’s performance as the first Black Catwoman, a film I loved that also received less than stellar reviews.

I don’t think any other song from the time period evokes the swagger that comes from female solidarity more than 702’s “Where My Girls At?” (1999). Lasting for more than thirty weeks on the charts, the Missy Elliott-produced song no doubt helped to shape today’s squad. Through a comparative analysis of music videos from the time period, scholar Rana Emerson concludes in “Where My Girls At? Negotiating Black Womanhood Through Music Videos,” that Black women did not accomplish their goals alone, but “looked to each other for support, partnership, and sisterhood.” At a time when singular white female musicians were rising to prominence, musicians from this time period brought me back to the importance of collectivity. Though the lyrics might not pass the Bechdel test, the song ultimately transcends the jealous woman narrative and instead speaks to a basic tenet of sisterhood—the desire to be backed up.

Twenty years later, TLC’s “Unpretty” (1999) still tears me up with its goodness. The video gets very real by grappling with issues commonly thought of as only pertaining to white women, like body positivity, bullying, eating disorders, and plastic surgery—but all through a Black woman’s lens. As a South Asian, my struggles with body insecurity are also intrinsically tied to my identity—I was bullied relentlessly as a child for being hairy and for having a unibrow. By elevating feminist issues to the forum of a music video, TLC manages to help normalize empathy and make it a quality worthy of possessing.

It is impossible to speak about the music of the millennium and the swagger it inspired without acknowledging the game-changing contribution of Destiny’s Child. The group persistently managed to narrate my own Bildungsroman through each of its hits. Struggling financially? Everyone coupling and you miss your BFFs? Deciding on a color scheme for your first apartment while simultaneously wondering if your man is cheating? Boo not as cool as you thought? In 1998, Destiny’s Child came out with “Bills, Bills, Bills,” “Jumpin’, Jumpin’” “Say My Name” (check out the video for décor tips), and “Bug-a-Boo.” All in ONE year. I think YouTube commenter Helene says best what we’re all thinking: “Damn Beyoncé was 18 here! And here I am lying in bed eating Cheetos, doing nothing with my life.”




There’s no more tears

Left here for you to see.




Despite my fears, I made it through the 2000s. It’s twenty years later, and I am still horrified—if not more so—by the systems. I always return to Whitney holding my gaze, challenging me to underestimate myself. I think of her plum lipstick, her majestic silhouette, and the narrative of her hands now when I walk into a college classroom  with the presumption that I have something to teach these students who have already seen so much. I think of her when I resist falling into the comfort of being a meek South Asian who forgets her liberation is tied up with that of so many others. When I battle imposter syndrome in all its incarnations.

Back then, the musicians of the millennium formed my ethos and regaled me with the glory of self-acceptance and its remarkable companion, swagger.

Now, my husband and I watch our biracial Indian-Mexican preschooler strum a tiny guitar and belt “Karma Chameleon” and “Life is A Highway” from deep in his soul—he’s moved past “Wheels on the Bus” and “Baby Shark”—and I think about when I’ll introduce him to this music that I love so much.

But for him, I want more than swagger—I want the impossible. For him, I want music that will make the world both right and okay.



Simona Supekar lives in Los Angeles and teaches Creative Writing and English at Pasadena City College. She received her MFA in Creative Writing from UC Riverside-Palm Desert and a B.A. in English and Anthropology from Oberlin College. Her work appears in The Atlantic, The Los Angeles Review of Books, and elsewhere. She is currently trying to find an agent for her first novel.

[1] Chang, Curtis. “Streets of Gold: The Myth of the Model Minority.” Rereading America: Cultural Contexts for Critical Thinking, Fourth Edition. Edited by Gary Colombo et al. Bedford Books. 1999. P. 366-373.

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