When Ray of Light was released on February 22, 1998, Madonna's image hit the ground and shattered into a flock of blackbirds.

Gone was Madonna the preening, winking, fun-loving vamp, replaced with a woman who was aggressively insightful and daring. If Like a Prayer revealed that Madonna had depth all along, the William Orbit-produced Light showed she had breadth: The woman who initially turned to music because it was the medium with which she could grab the most eyeballs the quickest, revealed herself to be more adventurous than ever, drawing from such far-flung sources as ‘70s glam rock, Eastern mysticism, and electronica—and risking her status as the Queen of Pop.

Selling more than 16 million copies worldwide, Ray of Light won the Grammys for Best Pop Album (her first musical Grammy), and the title track nabbed Best Dance Recording and Best Short Form Music Video. (It was also named Video of the Year at the 1998 VMAs.) The album remains singular in her career—and in pop music—and seems increasingly unlikely to be topped by its architect.

But let’s hope she never stops trying.

In honor of Ray of Light’s 20th anniversary, we asked Madonna expert Matthew Rettenmund (author of Encyclopedia Madonnica) to rank the album's tracks. His choices will likely inspire joy and fury in equal measure, but picking your favorite Ray of Light song is like picking your favorite boy toy.

"To Have and Not to Hold"

There are arguably no bad songs on Ray of Light, so it boils down to picking the least brilliant. This Rick Nowels co-creation has a pre-Dido lilt and is shimmery-pretty, but there’s that too-easy "moth to a flame" lyric.

"Swim"

Orbit and Ciccone’s rocky ditty is the second track on the album, hitting us with lyrics about "Children killing children / While the students rape their teachers." It’s an undeniably catchy number (the lyrics made less disconcerting by the lolling beat), but it feels like a wind-up before a pitch.

"Candy Perfume Girl"

Madonna was a huge Prince fan, and collaborated here with Prince protégée Wendy Melvoin’s twin, Susannah Melvoin. The song’s impressionistic lyrics hardly get in the way of its punk-rock edge, but a company called Magnetic Poetry accused the icon of using its product—a collection of fridge magnets bearing random words—to compose this minimalist guitar grind.

"Shanti/Ashtangi"

Reflecting her embrace of yoga, Madonna and Orbit crafted this Eastern delight, adapted from the work of Adi Shankara. Produced before the current fervor over cultural appropriation, “Shanti/Ashtangi” remains a pure example of Madonna using her platform to expand the hearts and minds of teenagers desperately seeking cruising jams.

"Little Star"

Written with Nowels during the first year of Lourdes’ life, this adult-contemporary lullaby oozes maternal pride. Twenty years later, her bond with Lola is still unshakeable.

"Has To Be"

Never heard of it? Fake fan! "Has to Be"—the only song on the album written by Madonna, Orbit and Leonard—appears just on the Japanese import, which is inexplicable because it’s a haunting ballad as vulnerable as anything she’s ever recorded. Perfect on a mixtape with Chris Isaak’s “Wicked Game."

"The Power of Good-Bye"

A chilly throbber that grabs you from the opening line, "Your heart is not open / So I must go," this hit single reached Number 11 in the U.S. and Number 6 in the U.K. It showcases Madonna’s post-Evita vocal control: While some object to the formality of her new phrasing—that hard R, though!—it serves this symphonic no-more-love song well.

The video, shot by Matthew Rolston and co-starring Goran Višnjić, is a secret remake of the Jean Negulesco-directed Joan Crawford masterpiece, Humoresque (1946).

"Nothing Really Matters"

Written with Patrick Leonard, with whom Madge created most of her best songs, “Nothing Really Matters” uncannily incorporates her newfound interest in the profound with her dance-floor origins, melding a high-drama electronic slam with house music all night long. The album’s most cheerful song, it was nonetheless a chart dud as a single (hitting just Number 93 in the U.S.).

The absolutely bonkers music video by Johan Renck allowed Madonna to both exorcise her obsession with the novel Memoirs of a Geisha (she reportedly imagined starring in the film adaptation) and to force some subversive imagery into young eyes seeking something less challenging. The choreography owes a hat tip to Elaine Benes, in the best possible way.

"Mer Girl"

One of the most avant-garde songs of Madonna’s career, this intensely emo prose poem set to dissonant blips and beeps plunges into the singer’s psyche as a child whose mother died young. It's like that Truth or Dare scene in which she lies on her mother’s grave, but if she started digging once there. "I ran and I ran/ I was looking for me" could be the title of her autobiography. Maybe more impressive than enjoyable to some.

"Skin"

This Madonna-Patrick Leonard scorcher undulates as it ponders her limitations as a communicator, arguing instead for the instant connection of skin-to-skin contact.

"I'm not like this all the time," Madonna warns—and she wasn't kidding.

"Sky Fits Heaven"

An urgent, upbeat track written by Madonna with Leonard, "Heaven" unfurls like a nervous heartbeat as she quotes prophets and wise men. Madge effortlessly multi-tasks, imparting wisdom while infecting us with a need to move. The most egregiously underserved track on the album, in that it was never a single anywhere. Listen for the “Bedtime Story” echo.

"Ray of Light"

Ranking one of Madonna’s signature singles in the context of the album from whence it sprung is tough, but “Ray of Light” is truly special. Reaching Number 5 on the U.S. charts, the song was derived from the 1971 tune “Sepheryn” by Curtiss Muldoon, adapted by Madonna as an orgiastic declaration of freedom and transition. Its primal scream is one of the best moments in the studio.

Her live take on The Oprah Winfrey Show, is unforgettable, as much for Madonna’s A+ vocal as for Oprah’s cute, B- dancing.

"Drowned World/Substitute for Love"

Beginning with a sample of Jesse Pearson uttering “You see” from a beatnik Rod McKuen song, this slinky, methodical deconstruction of Madonna’s rock-star life denounces fame, starfuckers, and sex in favor of family. (It's one of her favorite things she’s ever written, and easily her best Orbit co-composition on Ray of Light.)

The song climaxes with anger before ending with what seemed at the time like an embrace of a permanent post-siren image. "Drowned World" wasn’t a U.S. single, but the Walter Stern-directed music video, which referenced the recently departed Princess Diana, has to be in the Top 10 of her work in that medium.

"Frozen"

The best song on Ray of Light? This career-changing hit (Number 2 in America) written with Leonard effectively turned the page on all Madonna had done before, sounding, as it did, like nothing else on the radio. “Frozen” is one of Madonna’s most beautiful tunes, contains some of her most simply insightful lyrics (“You’re frozen / When your heart’s not open") and spawned a haunting Chris Cunningham-directed music video reintroducing the singer as a black-haired desert diva in triptych, covered in henna, undulating like Martha Graham.

“Give yourself to me,” she implored, and we all did.

Below, true-blue Madonna fans discuss the impact of Truth or Dare on their lives.