Madonna’s Best VMA Looks Prove She’s the Queen of Pop

1989: “Express Yourself”

At the 1989 VMAs, Madonna performed “Express Yourself” from her “Like a Prayer” album and it’s regarded as one of the best performances of the awards show’s history as well as her own.

“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,” Rolling Stone observed in 2017.

1990: “Vogue”

Madonna’s performance at the 1990 VMAs is one of the most iconic moments in the history of the awards show. The performance took place on September 6, 1990, at the Universal Amphitheatre in Los Angeles, California.

Madonna performed her hit song “Vogue” at the 1990 VMAs. The performance was a lavish production inspired by the golden age of Hollywood and featured Madonna and her backup dancers dressed in glamorous, black-and-white costumes. One of the most memorable moments of the performance came when Madonna, dressed in a Marie Antoinette-inspired outfit, descended from a giant wedding cake prop.

1993: Erotica

Madonna’s appearance at the 1993 VMAs is another notable moment in her career. The awards show took place on August 26, 1993, at the Universal Amphitheatre in Los Angeles, California.

Madonna opened the show with a performance of her single “Bye Bye Baby” from her controversial album Erotica. The performance was a provocative and highly theatrical routine that included elements of bondage and sexuality, being joined on stage by a troupe of dancers dressed in fetish-inspired attire.

1984: “Like A Virgin”

Madonna’s first appearance at the MTV Video Music Awards (VMAs) took place in 1984. She performed her hit single “Like a Virgin” during the inaugural VMAs ceremony, which was held on September 14, 1984, at Radio City Music Hall in New York City.

Madonna’s performance at the 1984 VMAs is one of the most iconic moments in the history of the awards show. She began the performance atop a giant wedding cake dressed in a bridal outfit, complete with a wedding veil and lace gloves. “So I thought, ‘Well, I’ll just pretend I meant to do this,’ and I dove on the floor and I rolled around,” the singer explained later. “And, as I reached for the shoe, the dress went up. And the underpants were showing.”

1994: Video of the Year presenter

During the 1994 VMAs, Madonna presented the award for “Video of the Year.” She also introduced a video montage highlighting the work of David Fincher, a prominent music video director with whom she had collaborated on several occasions, including the videos for “Express Yourself” and “Vogue.”

2003: *That* Kiss

Madonna’s performance at the 2003 VMAs was a reimagining of her classic hit “Like a Virgin,” which she originally performed at the inaugural VMAs in 1984. For this performance, Madonna appeared on stage dressed as a groom, and Britney Spears and Christina Aguilera, who were dressed as brides, joined her.

The performance began with Spears and Aguilera performing “Like a Virgin” in bridal attire, paying homage to Madonna’s iconic 1984 performance. Then, Madonna descended from above, wearing a black tuxedo and a top hat, and sang her 2003 single “Hollywood,” which is from her “American Life” album. The performance also featured *that kiss* between Madonna and Britney Spears, as well as one between Madonna and Christina Aguilera.

2021: Hell for Leather

Keeping with her trend of shocking everyone, this leather look might be one of our personal faves, plus who can deny a Burberry trench? Chef’s kiss.