Twenty-five years ago, I found myself having coffee with manager/musician Fenton Bailey, who tried to convince me that a young drag queen client of his — RuPaul Charles — was going to become America's next sweetheart. "He's lovable, he's larger than life, and he's going to change the world," Bailey told me (or something to that effect) at the time.

Good luck with that, I thought. For one thing, to call someone a drag queen in 1993 was a flat-out slur in many people's minds — even within the gay community. At the time, RuPaul was known only to the denizens of New York's still-edgy gay night scene, a demimonde that happened to include yours truly. Even so, I knew what Ru was up against. LGBTQ life back in those benighted days bore scant resemblance to what it does now. At the time, hardly anyone even addressed the "t" or "q" parts of the LGBTQ acronym. This was decades before gay marriage. Or the "It Gets Better" campaign. Or trans rights of any kind. Hardly any gay characters appeared on TV or in movies. If they did — as in Oliver Stone's JFK or the Sharon Stone top-lined Basic Instinct — they were often despicable villains lurking in the shadows. A more progressive movie like Brokeback Mountain was still 21 years away. The only appealing gay person you saw on television at the time was MTV's Pedro Zamora of The Real World, who later died from AIDS-related complications (1993 was also the peak year for new AIDS infections in the U.S., according to the Center for Disease Control). Small wonder that, within the music business, even eventual gay icon George Michael cowered in the closet for another five years — and he only came out, somewhat involuntarily, after he was entrapped in a sex act in a public bathroom.

Amid that stifling atmosphere, what chance did RuPaul have of breaking through — especially in his next guise — as a budding recording star? On June 8th, he dropped his first album, Supermodel of the World, a brazenly fierce, wildly sashaying bid to become every bit as big a superstar as its title imagined. The goal seemed insane at a time when the next mega music act would turn out to be the jock-rock band Hootie & the Blowfish, with their 1994 multiplatinum-selling debut record.

Yet Supermodel, led by its pivotal single/lifestyle slogan, "Supermodel (You Better Work)," did manage to strike a crucial, first blow against a drag-resistant world, while also making major inroads during a far more homophobic time. Seen from a modern perspective, RuPaul's debut seems even more daring and encompassing than it did in its day. It cut across several key subcultures, forcing them closer to the mainstream by sheer will and charm. That last factor would prove crucial to RuPaul's wider ascension and impact. "I knew this was happening for me when I was shooting the ‘Supermodel' video in Central Park and I had a Winnebago," he told EW in a 2017 interview. "I thought, I have a freaking Winnebago. I am here."

Bailey once told me that part of Ru's charm was his friendly approach. "RuPaul is basically Big Bird from Sesame Street," he said. "He's non-threatening and family friendly." But you'd be gravely mistaken to confuse "non-threatening" with wimpy or ineffective. In fact, RuPaul's career argues stirringly for the power of the "you draw more bees with honey" strategy. He killed them with sweetness. The fetching beats, witty lyrics, and winning melodies in his music didn't hurt either. All could be found in abundance on Supermodel. Its title single became an instant club classic, italicized by a plethora of snap-ready tag lines, including "you better work," "I have one thing to say," and "Sashay/Shantay!" each repeated with intensifying attitude. That last term drew from the world of drag balls, a historic underground culture first revealed to the larger world three years earlier by Jennie Livingston's eye-opening documentary Paris Is Burning. Madonna spread word of that subculture further with "Vogue," and its accompanying music video.

But Madge merely served as a translator of a pre-existing world, while RuPaul had a deeper connection to it, giving him the authoritative advantage. His hit brought to the fore three cultures — drawn from black, gay, and drag experience — serving them with a purity you seldom get in pop culture crossovers. The combination gave the song great specificity, while its thumping, pumping house beat, and Ru's easy-to-repeat mantras, lent it universality. And then there was Ru's singing. He wasn't just a figurehead for the song. He got inside it, in a voice graced with its own kind of soul.

"Supermodel," went on to sell over 500,000 copies, while its music video finessed Ru onto MTV. By the fall of 1993, Kurt Cobain gave the cut a shout-out as one of his faves of the year, and he and Ru were photographed later at the Video Music Awards (back when that really meant something).

The hit was hardly the album's only highlight. "Back To My Roots," which hit No. 1 on Billboard's Hot Dance Club chart, heralded "a hair revolution," valorizing a wide variety of architectural black hair styles, from "finger wave" to "blacktop fade." "Peace, love, and hair grease," Ru declared, creating another catch phrase for the ages. The line was funny but it was also socio-politically potent, asserting a follicle-y minded reclamation of respect for black beauty. Ru did this years before Beyoncé would start making such declarations a hallmark of her character and presentation. If all that wasn't enough, the album also offered "Stinky Dinky," a Rick James-like dive into skanky love, and yet another slogan of death: "The future belongs to those who can smell it coming."

Image zoom Porter Gifford/Liaison/Getty Images Porter Gifford/Liaison/Getty Images

Ru credits his appearance on The Arsenio Hall Show that year with fanning his fame with wildfire swiftness. In '94, he became the first drag queen to receive a major cosmetics campaign contract (for MAC), leading to him landing his own talk show on VH1, the first time an openly gay person had gained such a platform. The program enjoyed a 100-episode run, airing alongside Ru's co-hosting gig on New York's powerful dance station, WKTU. In 2009, he debuted RuPaul's Drag Race, a show that's been on for almost a decade and eventually bagged its star an Emmy. Along the way, Drag Race made drag queens as common as prom queens, drawing swarms of straight young women to their side. In fact, so many such folks have begun to flock to gay bars around the country, they've sometimes crowded out the original patrons. (Small wonder I found myself writing a piece for the New York Times last year titled "How Gay Should a Gay Bar Be?")