Watch: Madonna Remembers Career-Ending Performance on 'The Tonight Show Starring Jimmy Fallon'

by Emell Adolphus

EDGE Media Network Contributor

Saturday August 13, 2022
Originally published on August 11, 2022

Madonna shows off her grillz on "The Tonight Show Starring Jimmy Fallon"
Madonna shows off her grillz on "The Tonight Show Starring Jimmy Fallon"   (Source:YouTube)

During an appearance on "The Tonight Show Starring Jimmy Fallon," Madonna remembered the moment everyone thought her career was dead on arrival like it was yesterday—except it was in 1984 at the very first MTV Video Music Awards.

She performed, what went on to become a breakout hit, "Like a Virgin" and lost a shoe while onstage. She tried to surreptitiously and seductively retrieve the stiletto and ended up with her dress above her butt.

The moment is iconic, but at the time her then-manager Freddy DeMann said her career was over.


"Those were the days when you shouldn't show your butt to have a career," Madonna joked. "Now it's the opposite... I didn't even know my butt was showing!"

The performance, of course, didn't come close to ending her career and launched her to the throne of pop.

Madonna was on the show to promote her new remix album of all No. 1 hits titled, "Finally Enough Love."

Giving everyone a full dose of Madonna, she sung "Music" while playing classroom instruments with the "Tonight Show" band, talked about getting grillz for her birthday and played a sultry game of word association with Fallon.

See the funny moments below.