Madonna at 60: Her Greatest Pop Moments

For nearly four decades, Madonna has shocked, titillated, outraged, disgusted, enamored, confounded and thrilled with her indomitable presence and crackerjack pop sensibilities. No one could’ve imagined back in the days of “Lucky Star” that she would fulfill her promise on American Bandstand and thoroughly conquer the world. Well, of course Madonna did. No matter what your opinion of her is (and there are many to be had), her impact is undeniable. In honor of the Queen of Pop’s upcoming 60th birthday, I’ve gone through her extensive catalog and picked the singles that showcase why she is a singular presence in pop music. Yes, some classics are missing, but the below records truly are Madonna at the height of her unique powers.

Holiday (1983)

Madonna’s first legitimate hit isn’t anything special on its own; it’s a simple, frothy ditty about breaking free from life’s troubles and enjoying life’s pleasures. It’s Madonna’s charismatic performance, deceptively sweet and brimming with the latent sensual energy that would burst forth just one album later, that elevates “Holiday” from forgettable pop trifle to an 80’s classic that only she could pull off.

Material Girl (1985)

After rolling around in a wedding dress at the inaugural VMAs, it was easy for most to dismiss Madonna as just another pop tart with a knack for getting people’s attention. Those people also likely missed the biting send-up of 80’s capitalist excess that was “Material Girl”, preoccupying themselves instead with the video’s glamorous Marilyn Monroe tribute (a send-up in and of itself). The “material girl” moniker may be the song’s enduring legacy (much to her chagrin), but it also signaled that Madonna was a lot smarter than she was given credit for.

Live to Tell (1986)

Anyone who thought they had Madonna pegged was definitely thrown by “Live To Tell”, the lead single from the blockbuster True Blue album. The stunning ballad marked the first of many Madonna reinventions, from “Boy Toy” to poignant songstress. Backed by stunning production from longtime collaborator Patrick Leonard, Madonna digs deep into lyrics of betrayal and its lingering effects to deliver a stirring performance that, thirty years later, still resonates.

Open Your Heart (1986)

Much of Madonna’s early pop output buzzed with an undercurrent of Reagan-era cynicism about love, sex, money and general human emotion. True Blue broke the mold by wearing its heart on its sleeve. “Open Your Heart” led the way, with an unabashed call for affection that was accompanied by her purest pop production to-date. Madonna asked us not to resist her, and it was becoming harder to do so by the minute.

Like a Prayer (1989)

Madonna has been in open rebellion against the Catholic tradition for most of her career, with multiple Vatican bans to prove it. Her most enduring religious controversy centered around “Like a Prayer”, an ebullient celebration of life and love that was the perfect capper to the decade of decadence. It is also happened to conflate prayer with oral sex and had a music video where she made out with a black Jesus. The furor was so great that Pepsi infamously paid Madonna to cancel her contract, making it the easiest paycheck of her career. Ignoring the sacrilege, “Like a Prayer” is barn-storming pop perfection that uncovered new depths to Madonna’s talent.

Vogue (1990)

A glossy, high-glam house track that paid tribute to old Hollywood and borrowed heavily from New York queer ballroom culture, “Vogue” was a global sensation that also served as the manifesto of Madonna’s blond ambition. Excellent on its own, the song reached stratospheric heights with its instantly iconic black-and-white Art Deco-style music video. No other single in the Madonna canon encapsulates the essence of her pop genius better than “Vogue”, making it her crowning achievement.

Justify My Love (1991)

Yes, the music video scandalized America and sent MTV into one of its many Madonna-related meltdowns. Yes, it is exposed America’s absurd hypocrisies about sex, especially in regards to women. Yes, Madonna rode the controversy straight to the bank. All of that aside, “Justify My Love” is legitimately one of the sexiest records in pop history. Through gauzy, trippy house beats and a breathy spoken-word vocal, Madonna explores the underpinnings of desire with aplomb, leaving even the most repressed individual warmer under the collar. “Justify My Love” and its infamous visuals shredded the proverbial envelope and forever changed the relationship between sexuality and pop music.

Erotica (1993)

“My name is Dita; I’ll be your mistress tonight”. Never has an introduction been so seductive and menacing in equal measure. The title track of Madonna’s most controversial album is pop’s first kink negotiation, taking the sexual exploration of “Justify My Love” to its logical extreme. Madonna role-plays as Dita, a breathy, icy dominatrix who engages listeners in a frank discussion of pleasure’s darker impulses, over Shep Pettibone’s hypnotic production and a killer hook. Hindsight has been a lot kinder to “Erotica” (for starters, it wasn’t nearly as explicit as the negative reaction suggested), and both the song and its parent album are credited for ushering in a new sexual revolution that every female pop star who followed Madonna has benefitted from.

I’ll Remember (1994)

It was 1994: Madonna desperately needed a reboot after the Erotica era, and Warner Bros. desperately needed a hit single for its coming-of-age drama With Honors. The result of such advantageous timing was “I’ll Remember”, a reflective, restrained tribute to past love. With Honors is long lost to the public’s consciousness (and probably to both Madonna and Warner Bros.), but “I’ll Remember” ranks amongst her best ballads, thanks in part to the return of frequent collaborator Patrick Leonard (responsible for her best ballad, “Live to Tell”). More than just the perfect post-Erotica palate cleanser, “I’ll Remember” was the precursor to the mature phase of Madonna’s career.

Bedtime Story (1995)

At her best, Madonna has a knack for being at least two years ahead of the rest of pop music. Take, for instance, the title track from the oft-overlooked Bedtime Stories album. Penned by Icelandic pop provocateur Bjork, “Bedtime Story” is an audacious, entrancing acid trip through a dreamscape of warped, warbling beats and synths that is a startling outlier amongst the album’s seductive R&B ballads. The song is but a brief taste of the electronica that Madonna would fully embrace on 1998’s Ray of Light. Understanding the track’s importance to her future, Madonna gave it the full single treatment, complete with excellent Junior Vasquez remixes and the most ambitious and strange music video of her career. Pop music had never been so absorbingly weird, and hasn’t been since.

Frozen (1998)

The promise of “Bedtime Story” three years prior was fully realized with “Frozen”, the lead single from the landmark Ray of Light. Once again upending what a Madonna song is supposed to sound like, she puts William Orbit’s cinematic strings and ambient beats, as well as her post-Evita vocals, to excellent use on this sweeping, haunting ballad. “Frozen”, with its overt darkness and subtle spiritual undertones, was definitely a risk, but it paid off in spades, granting Madonna the best of both worlds: commercial success and, more elusive to her, critical acclaim.

Ray of Light (1998)

Spirituality, born from her study of the Kabbalah faith, runs deep through the Ray of Light album. But instead of letting it overtake and overwhelm her, Madonna channels this newfound energy through the vessel of electronica. The album’s title track is a frenetic blast of club-ready euphoria, nearly bursting at the seams. Madonna, ever the control freak, lets loose here like never before, delivering the most joyous, cathartic vocal of her entire career. “Ray of Light” is an exhilarating, astounding height, and it’s a privilege to be taken along for the ride.

Hung Up (2005)

If American radio stations in 2005 were a little less uptight, “Hung Up” would’ve gone to #1, like it did everywhere else. Realizing the damage done by her foray into lazy socio-political commentary, Madonna went back to her roots for Confessions on a Dancefloor. Built around an incredibly smart sample of ABBA’s “Gimme! Gimme! Gimme!”, “Hung Up” is a high-octane thumper that lit up club floors worldwide and showed that, 22 years deep into her career, Madonna had no intention of slowing down.