12 Reasons This Is Madonna's Best Performance Ever: VMAs 1989 (2025)

There’s a case to be made that there’s no such thing as Peak Madonna. Over the past three decades, the Queen of Pop has ascended so many summits, pulled off so many comebacks and, yes, reinvented herself so many times that it feels impossible to distill her essence into one defining moment. And yet. Back in September 1989, Madonna opened the MTV Video Music Awards at the Universal Amphitheater in L.A. – Arsenio Hall hosted, newbies Paula Abdul and Guns N’ Roses both had banner years and somehow Neil Young’s “This Note’s For You” won Video of the Year – with “Express Yourself.” In six minutes, Madonna, then 31, divorced from love-of-her-life Sean Penn and riding the commercial and critical success of her revelatory fourth album, Like a Prayer, spelled out to audiences that night why she was (and always will be) one of the most electrifying, charismatic pop stars and live performers of all time.

1. The killer opening sample is so meta. Before self-referential everything and throwbacks became ubiquitous pop tropes, here, in the crackling open moments, we hear a somewhat-obscure bridge (“Dance and sing/Get up and do your thing”) from Madonna’s very first single, 1982’s “Everybody,” which she sang at downtown Manhattan clubs like Danceteria, spliced into the bass line. It’s not simply a clever, tight bit of sampling: It’s also a signal that our queen, then just five years into her superstardom, is already aware of the musical legacy she’s building. This is muscular, established 1989 Madonna, but her beauty mark, those winks and kick-intensive choreography also signal thatthis is the I-want-to-rule-the-world ingenue of “Lucky Star” – and the even bolder, openly defiant, postmodern empress yet to fully reveal herself.

2. Her chair work is top-notch.Before Janet Jackson (“Miss You Much”) and Britney Spears (“Stronger”) but definitely after any number of participants in a Bob Fosse joint, our heroine first showed her mastery of chair-ography in 1986’s “Open Your Heart” video, playing a tables-turning peep-show stripper. Even in silhouette, those preening, contorting shadows could only be hers. That’s iconic.

3. And her stair work is even better.Never, ever, never underestimate the power of magical light-up stairs(an evolution of the sidewalk in Michael Jackson’s “Billie Jean” video) to set the mood. No modern entertainer has descended (and, later, ascended) steps with as much precision or joie de vivre. Just ask the cheering crowd in the Universal Amphitheater what they think.

4. She’s got the best wing-women in the biz. Who are these two other ladies? Glad you asked. Niki Harris (to Madonna’s left) and Donna De Lory (to her right) were Madonna’s principal, fan-beloved backup singers on her albums in the late Eighties and Nineties. Harris recorded the gospel solo in “Like a Prayer,” and both provide gorgeous, timeless harmonies on “Express Yourself,” “Vogue,” “Rain” and other hits, helping to define her vocal style during this era. They also accompanied her on numerous tours as her spirited, bantering ladies-in-waiting.

5. It’s a sneak peek at a world-conquering tour. Most famously, Niki and Donna were Madge’s sidekicks on the Blonde Ambition Tour, which would kick off about a half a year after this VMAs turnand documented in 1991’s Truth or Dare. This theatrical, girl-powered, slyly subversive VMAs performance sets the template for that historic trek, featured on Rolling Stone’s 50 Greatest Concerts of the Last 50 Years list. In fact, the concert opened with a more expansive and elaborate version of the “Express Yourself” routine (adding Gaultier cone bras, shirtless hot men, more visual elements from David Fincher’s Fritz Lang–inspired video and lots of humping .)

6.Her vocals aren’t perfect, but they’re the real deal. Madonna shrewdly never marketed herself as a singer with Whitney Houston–level pipes. But the woman who would, in the next decade, breathe life into songs written or co-written by Stephen Sondheim (I’m Breathless), Babyface (Bedtime Stories), Andrew Lloyd Webber (Evita) and a wide swathe of proto-EDM producers (including Ray of Light’s William Orbit) brings fervent, soulful conviction and attitude to her strongest vocals. She may have a backing track here, but Madonna is assuredly not lip-syncing, aerobic routine or not. (The following year, in another classic but less off-the-cuff VMAs performance, she’d lip-sync “Vogue” entirely as Marie Antoinette.)

7. That song, though. Nearly 30 years on, beyond being simply a perfect, gotta-dance pop creation, “Express Yourself” remains one of Madonna’s most trenchant feminist anthems. We’re talking top three. It advances the theme of female sexual empowerment laid out in “Like a Virgin,” which extolls a skillful lover who makes her feel “shiny and new” and “so good inside.” In the brassy, clubby “Express Yourself,” she instructs romantically challenged girlfriends to demand respect and communication as well as transcendent orgasms from their men: “Make you feel like a queen on a throne/Make him love you ’til you can’t come down.”

8. Can we talk about her hair? We’re going to talk about her hair. Of all the Madonna cuts and hues we’d seen up to this point and the ones we had yet to see, this one – shaggy, tousled beachy blonde with dark Italian-girl roots showing – might be our favorite. Because the more she sweats and messes it up, the sexier it looks.

9. Actually, the whole look is really special. One more thing about the hair: It perfectly sets off the androgynous baggy suit, with trademark underwear-as-outerwear peaking beneath, and Jacko-esque black penny loafers (with white socks). And while Madonna’s most famous accessory will always be the crucifix, the dangling gentlewoman’s monocle – another reference to her Lady Factory Boss character from the video – sure is fun.

10.Madonna does the Roger Rabbit and the Running Man. Seriously. Around 3:08, after a masterful over-the-shoulder blazer-recovery move, the girls segue into their first extended dance break, in which Madonna murders the Roger Rabbit and the Running Man like the trained, intuitive dancer she is. Just look at her face: Has she ever looked freer or happier? This is a star.

11. There’s a must-see microphone-cleavage move – and first-time voguing.There’s another dance break (we love dance breaks!) around 4:10. After placing their microphones for safekeeping in a very novel (and sexy) place, there’s a slo-mo crotch grab. Wait, are they voguing? Alert: We’re pretty sure is the first time we’re seeing Madonna vogue in public. (“Vogue” the single would drop in March 1990.) Stay cool.

12.The sign-off is way better than a mic-drop. Not content with thunderous applause, she kicks that poor chair clear off the platform.Again, really outstanding chair work. Then, after a high-five, a panting, satisfied Madge and her girls exit stage left. She has one word: “Yeah.” Our thoughts exactly. The Eighties are over, the Nineties are here, and Madonna ain’t going nowhere.