1. In 2003, the Gap announced they had gotten Madonna, the ultimate a fashion icon, as the face of their fall campaign, called “A New Groove, A New Jean.”
Madonna wore Gap low rise cropped cords and a ribbed white tank top. She completed her look with $5 million in diamond jewelry from Neil Lane.
2. While Madonna was no stranger to fashion ad campaigns — she had famously been the face of Versace in 1995 — this was her first foray into a lower-end brand.
She has since then collaborated with lower-end fashion companies like H&M and Macy’s.
4. There was even a limited edition CD of Madonna’s latest single “Hollywood” (remixed by Missy), which of course was available exclusively at Gap stores.
5. But the most memorable part of the campaign was the catchy “Into the Hollywood Groove” commercial:
6. Mainly because Missy upstaged Madonna.
7. And she was not having it.
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