The year is young, but Grammy chieftain Neil Portnow’s suggestion that female artists need to “step up” will take some beating for tone-deafness. To help today’s heroines unseat the likes of Bruno Mars, he might look to the 1999 ceremony.

The 41st edition of the awards properly reflected the female energy coursing through late 90s mainstream music. Only one out of 10 nominees for the record and album of the year categories was male-fronted, while Shania Twain, Sheryl Crow and Garbage’s Shirley Manson were all in their mid-30s; The Miseducation of Lauryn Hill ran out eventual winner in the album bracket. Madonna, snubbed in any meaningful category for so long, also finally got her dues. She took home three for Ray of Light and its title track. But, if anything, the album’s stock was modest then compared to now.

Ray of Light is probably Madonna’s most widely acknowledged classic. It is held as a high-water mark of pop-as-art, a work that still rings out as believable and true from a star who adopts and discards phases, passions and philosophies at pace. That era of Madge inspired half a catwalk’s worth of memorable looks (she was variously a geisha, a gothic witch, a gap-year student and a raven-haired mother reborn over rushing skylines), with such a superabundance of hits that Sky Fits Heaven was withheld as a single so as not to cannibalise the title track’s success.

Last week saw an outpouring of celebratory 20th-anniversary articles; later this week, London gay club the Glory is throwing a two-stage celebration of everything Ray of Light. Even for a cabaret haunt, the amount of effort being poured into one-time-only tribute costumes speaks to the devotion of this period.

Madonna’s look for Frozen, recreated by Margo Marshall, who will appear at the Glory’s Ray of Light cabaret event. Photograph: Alexander Nunney

The album sold well in the US but didn’t exactly shatter the charts. By the end of 1998, it had sold just shy of 2.7m copies, ranking 18th in the Billboard end-of-year rundown. (Which illustrates how charged the market was then; last year’s bestselling physical release, Ed Sheeran’s ÷, managed sales of only 1.1m.) It’s consistently strong front-to-back, but only Frozen could reasonably be regarded as a contender for her greatest-ever song. William Orbit’s aquatic sound palette was a fine match, but so too was Mirwais Ahmadzaï’s mechanised funk on 2000 follow-up LP Music, yet Mirwais doesn’t field interviews about his impact to this day. So why does Ray of Light merit the obsession?

For one, the themes tackled are more complex than your usual dance-pop smash. She reconciles her complicit role as a bratty star in a male-controlled industry (Nothing Really Matters), the breakdown of love with Lourdes’ father, Carlos Leon (Frozen), and, purportedly, her stormy marriage to Sean Penn (The Power of Good-Bye). For Anna Cafolla, the Quietus pop critic who had an Irish-Catholic upbringing, the stark closer Mer Girl, wherein Madonna lets loose the weight of witnessing her mother’s overgrown grave, hit home hardest: “Lush, haunting, one I still feel particularly close to as a woman now … It also makes me want to give my own mum a really big hug.”

It’s easy to poke fun at Madonna extolling the virtues of Kabbalah and her subsequent legacy of faux depth, but this sells her short. “We didn’t have Instagram grids to analyse an artist’s psyche,” says Cafolla, “[so] you took the intimacy you got.” As a more open-hearted reinvention, Ray of Light also flipped the narrative that Madonna’s moment in the sun was over. A lengthy losing streak of public evisceration in the mid-90s through her cycle of Erotica, Sex and generally standoffish behaviour led her to pull back and exhumed some ghosts of old. As a moment of reflection and acknowledgment of her position in the pop landscape, Nothing Really Matters just about shades Bitch I’m Madonna.

Timing played a major part. “We all thought Y2K was plunging us into darkness and leprosy,” recalls John Sizzle, of the Glory’s queen bees and a Madonna diehard who claims to have attended every global tour but one. There’s no small irony in the fact that an album by arch-exhibitionist Madonna provided a soothing balm for frazzled pre-millennium nerves and a path back to “the basics of nature, love and spirituality”, according to Sizzle. There’s another irony, too, that by adopting a more passive mode she placed a renewed spotlight on her sharp talent and capacity for impact, and in doing so restored her seat at the high table of pop.

Britney Spears and Madonna kiss during the opening performance of the MTV video music awards in 2003. Photograph: Julie Jacobson/AP

Ray of Light now also represents something that was lost as much as gained. Alongside Lauryn Hill’s Doo Wop (That Thing), Shania Twain’s That Don’t Impress Me Much, Cher’s Believe and ever other defiant kiss-off that dominated 1998’s airwaves, something fresh began creeping into view as the year wound down, in the shape of Britney Spears’ Baby One More Time. It will forever be an all-timer, a hall-of-famer, a massive 24-carat belter; for that Grammy class of 98-99, it was also a silver bullet. Even the Spice Girls, whose Spiceworld film hit the US as Ray of Light made its mark on the Billboard charts, didn’t upend the global pop landscape in the way Britney did. The hard-earned space at the heart of mainstream music for adult women projecting maturity and strength came to an abrupt end, crushed by a teen-pop explosion. “All that rot,” as Sizzle would have it.

This era of doe-eyed fantasy objects soon led to the era of raunch. Britney and Xtina (née Christina Aguilera) became, says Cafolla, “a manufactured backlash, a response of assless chaps and porny pop videos”. Frustratingly, Madonna got sucked into this, playing catch-up in a way that seemed inauthentic and cheap – doubly unfortunate given her deep roots in New York’s transgressive underground. Tonguing both of her usurpers at the MTV VMAs in 2003 represents a sad moment of full-circle debasement. “Pop’s a tough ride,” laments Sizzle. “It was never meant to be performed by the over-30s – it was created for teens to consume. Teens don’t want to buy a record made by their saucy auntie, right?”

The ensuing 15 years haven’t been much easier on Madonna. The less said the better about MDNA’s desperate pitch to EDM-crazed America, Rebel Heart’s head-in-hands rollout, and American Life’s dire “three nannies, an assistant, and a bodyguard or five” rap. Ray of Light is rendered even brighter by comparison, one of those rare pop behemoths where all the stars align: right time, sound, artist, message and audience. You wouldn’t put it past her to hit on another winning late-career reinvention, although perhaps to simply rebuild her brand rather than seize the zeitgeist once more. But if that never arrives, we’ll always be able to revisit 1998’s Madonna, frozen in time.