10 Iconic Moments From Madonna’s Career

Videos by American Songwriter

Videos by American Songwriter

As the string of musical biopics continues to roll on, the Queen of Pop is doing what she does best—taking things into her own hands.

Madonna is gearing up to direct her own life story in what we can only assume will be a show of her larger-than-life vision that was a staple in her music videos and performances.

From shepherding the MTV generation to becoming a fully-fledged pop diva, Madonna is nothing if not iconic. Her road to the upper echelons of stardom was paved with so many unforgettable moments that we figure it was hard for Madge to pick and choose for the impending film. Below we recap just a few moments that we count as too iconic to leave out.

10. Madonna Releases Her First Music Video

Madonna is arguably the leading voice of the MTV generation. Her visuals pushed the envelope in the early ’80s—so much so that she quickly began to garner backlash from parents and several conservative interest groups. But before she was the rosary-wearing, wedding dress-ruining icon we know her as today. She was a fledgling popstar dancing in menswear amid a club for her first single, “Everybody.”

The video was uncharacteristically tame for Madge but, the insatiable disco beats were alive and well.

9. Madonna Stuns With “Like A Virgin” At The VMAs

When you think of Madonna, what comes to mind? For many people, it’s her atop a wedding cake in a deconstructed wedding dress for the VMA performance of her first No. 1 hit “Like A Virgin.” As she writhed around on the floor, people audibly gasped in the audience while she ran through the more-than-suggestive tune. The performance fully cemented her into the envelope-pushing pop phenom we know today.

8. Live Aid 1985

Madonna joined the famine relief effort in Africa by taking the stage at Philadelphia’s JFK Stadium for Live Aid. She showed off her light-hearted pop across three songs, “Holiday,” “Into the Groove,” and Love Makes the World Go Round”—The Thompson Twins and Nile Rodgers joined her for the final song.

While the concert, and its sister show in London, was an iconic moment in itself, Madonna’s appearance alongside the heavyweight artists marked her as one of the biggest singers of the era.

7. Madonna Gives a Provocative David Letterman Appearance

Never one to miss out on a chance to cause a little bit of a stir, Madonna took her first appearance on Late Night with David Letterman as cause to convince the world she was in a romantic relationship with actress Sandra Bernhard, who joined her on the couch.

If Madonna likes to do anything, it’s playing with the sexual boundaries of her time—an inclination that was in full force during the Letterman appearance. She walked out onto the show with Bernhard in matching jean shorts and white T-shirts, mouthing “I Love You” to one another. “We hook up, sometimes with Jennifer Grey,” Bernhard said during the provocative interview.

6. Blond Ambition World Tour

From the very first date of her Blond Ambition Tour, Madonna unveiled what would become her signature wardrobe selection—the cone bra. The undergarment, designed by Jean-Paul Gaultier, was worn during the opening part of the show above a pin-striped suit as Madonna hit the stage with “Express Yourself.”

The tour was also the debut of one of her most famous onstage moves, simulating masturbation on a bed to “Like a Virgin.” The move had the show banned in several locations—most notably Rome after the Pope called for a boycott.

5. Madonna Strikes a Pose with “Vogue”

Madonna created one of the biggest gay anthems of all time when she released “Vogue” in 1990. She then went on to revive an entire movement when she performed the track at the VMAs later that same year.

Complete with Marie Antoinette-Esque garb and a legion of backup dancers, Madonna contributed to bringing back Black and Latinx ballroom culture (voguing) into mainstream pop culture. The isolated, face-framing dance was first featured in the music video for the track before eventually making its way to the VMA stage for another iconic performance.

4. Sex and Erotica

Ever the sex-positive feminist, Madonna released a coffee table book in 1992 with the simple title, Sex. One could guess what was within the pages of such a book—the singer in a variety of R-rated positions alongside Vanilla Ice, Naomi Campbell, and Big Daddy Kane, among others. The bit of light reading was released in tandem with Erotica, a concept record about sexuality that earned a Parental Advisory sticker and a heated public debate.

3. Madonna Takes on Evita

Madonna moved on from the music video circuit to the silver screen when she took on the role of the Argentinian First Lady, Eva Perón, in Evita. The musical drama film is based on Perón’s rise in the political ranks before her death at age 33.

Her commitment to the role earned her a Golden Globe win for Best Actress—Motion Picture Comedy or Musical in 1997. This film, on top of her newfound motherhood and spiritual journey, would push her into her next big project, “Ray of Light.”

2. The Infamous VMA Kiss With Britney Spears and Christina Aguilera

In yet another unforgettable VMA moment, Madonna passed the torch to younger pop sensations Britney Spears and Christina Aguilera at the 2003 awards, leaning over to give each of the starlets a kiss while singing “Like a Virgin” together. Missy Elliot then jumped on stage for a quartet performance of “Hollywood” while the unsuspecting audience looked on in shock.

1. Rock N’ Roll Hall of Fame Induction

Madonna was honored for her contribution to music in 2008 with an induction into the Rock and Roll Hall of Fame. Fellow Michigan native Iggy Pop and the Stooges performed her “Burning Up” and “Ray of Light” tracks during the ceremony after an induction speech from Justin Timberlake, in which he joked about the pop star giving him a B-12 shot. “That’s what Madonna was and will continue to be for all of us: A shot in the ass when we need it most,” he said.

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