A Brief History of Madonna and the VMAs: ‘The House She Helped Build’

<img src="https://media-cldnry.s-nbcnews.com/image/upload/t_focal-760×428,f_avif,q_auto:best/mpx/2704722219/2026_09/1790336868716_tdy_pop_7a_ikeda_vmas_260925_S3_1920x1080-ab648r.jpg” alt=””>

Taylor Swift Drops 4 New Songs Ahead of VMAs Honor
03:19

“Catch Me Up” is a TODAY series where our experts and journalists bring readers up to speed on the day’s biggest headlines.

Where would the MTV Video Music Awards be without Madonna?

Madonna’s name is practically synonymous with the VMAs. She was there from the beginning, rolling around the stage in a wedding dress while performing “Like A Virgin” during the awards show’s 1984 debut.

Over the next four decades, Madonna returned to the VMAs to deliver groundbreaking performances. She’s also made headlines with outrageous antics — like French kissing Britney Spears onstage — and touched fans’ hearts with an emotional tribute to Michael Jackson after the musician’s death in 2009.

Now, the Queen of Pop is poised make a historic return to the 2026 VMAs on Sept. 27 when she performs at the awards show for the first time in 23 years.

Madonna’s performance will kick off the awards show for a record-breaking fifth time, ending her tie with Rihanna, who’s opened the show four times.

Madonna who released her hit album, “Confessions II,” in July, also goes into this year’s VMAs as the most nominated performer.

The singer is “returning to sit on her throne for the night,” NBC News entertainment contributor Chris Witherspoon tells TODAY.com.

“You simply cannot tell the story of the VMAs without telling the story of Madonna. From ‘Like a Virgin’ in 1984, to ‘Vogue’ in 1990, to that unforgettable 2003 performance with Britney Spears, Christina Aguilera and Missy Elliott, Madonna understood the assignment before we even had the phrase,” said Witherspoon.

“Madonna returning to the VMAs doesn’t feel like a comeback to me. It feels like the Queen of Pop returning to the house she helped build,” Witherspoon added.

Ahead of Madonna’s triumphant VMAs return, let’s take a look back at her 10 biggest moments at the awards show.

1) The Wedding Dress Seen Round the World (1984)

Madonna’s audacious performance at the inaugural MTV Video Music Awards in 1984 — she rolled around the stage in a punky ensemble that includes a wedding dress, rosary beads and a “Boy Toy” belt buckle — became her breakout moment.

The raunchy performance, which also included some bumping and grinding, also branded the VMAs as a rebellious alternative to the Grammys and other awards shows.

“MTV could barely fill the seats at the VMAs in year one. By year two, pretty much every act wanted a spot on that stage. Madonna was at the first show in 1984, rolling across the stage in a wedding dress singing ‘Like a Virgin.’ I’d give her a lot of credit for that turnaround,” Jeff Moore, a music marketing strategist, professor, and former touring musician, told TODAY.com.

2) Madonna Expresses Herself (1989)

Madonna returned to the VMAs five years later to deliver one of her finest televised performances when she sang “Express Yourself” with her two backup singers-dancers.

The newly divorced singer — her marriage to Sean Penn officially ended earlier in the year — began her high-energy, tightly choreographed performance wearing a dark suit before stripping down to a corset.

3) ‘Vogue’ Meets the French Revolution (1990)

The former Material Girl’s breathtaking 1990 performance of “Vogue” was inspired by the French Revolution. Madge as Marie Antoinette? Oh, it worked, right down to her and her dancers’ 18th century-style powdered wigs, heavy white face makeup and corseted gowns.

4) ‘Ray of Light’ with Lenny Kravtiz (1998)

In what’s considered one of the best live performances, Madonna showed off her vocal chops on the soaring “Ray of Light’ with guest guitarist Lenny Kravitz during the 1998 show.

The singer, who kicked off the performance with the Hindu-inspired “Shanti Ashtangi,” also swept the awards that night, taking home five Moon Man trophies.

5) Madonna Meets Her Drag Impersonators (1999)

The singer was feted the following year by a group of drag queens who wore some of her most memorable looks as theylip-synched and danced to her greatest hits.

“All I have to say is that it takes a real man to fill my shoes!” the singer quipped afterwards.

6) Kissing Britney Spears and Christina Aguilera (2003)

In 2003, Madonna shocked viewers when she took a moment during a throwback performance of “Like A Virgin” to kiss shared her guest performers Britney Spears and Christina Aguilera.

Spears and Aguilera donned skimpy wedding dress looks in a fun nod to Madonna’s debut VMAs performance.

7) An Emotional Tribute to Michael Jackson (2009)

Madonna showed off her serious side when she paid an emotional tribute to her late fellow pop icon Michael Jackson at the 2009 VMAs, calling Jackson “one of the greatest talents the world has ever known.”

“His music,” she said in her speech, “had an extra layer of inexplicable magic that didn’t just make you want to dance but actually made you believe you could fly, dare to dream, be anything that you wanted to be.”

She also recalled going to dinner with Jackson years before.

“Later we went back to my house to watch a movie and sat on the couch like two kids, and somewhere in the middle of the movie, his hand snuck over and held mine,” she said. “It felt like he was looking for more of a friend than a romance, and I was happy to oblige. In that moment, he didn’t feel like a superstar. He felt like a human being.”

8) A Surprise Appearance, Motherf—–! (2021)

Decked out out black dominatrix bodysuit and cap, Madonna made a surprise appearance to open the 2021 VMAs.

The singer’s appearance came just after viewers watched a short video telling the story of her arrival in New York City decades before with just $35 to her name.

Madonna then walked out onstage, telling the crowd, “And they said we wouldn’t last. But we’re still here, motherf——!”