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.” Via madonna.com 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. 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. Via madonna.com She has since then collaborated with lower-end fashion companies like H&M and Macy's. Missy Elliot also fell into the Gap. Via madonna.com 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. Via tokyomusicjapan.com But the most memorable part of the campaign was the catchy “Into the Hollywood Groove” commercial: View this video on YouTube Mainly because Missy upstaged Madonna. Tap to play or pause GIF Tap to play or pause GIF And she was not having it. Tap to play or pause GIF Tap to play or pause GIF In the end it all paid off -- Madonna helped the chain get their financial groove back.