After meeting Madonna for the first time, it appeared their friendship blossomed really quickly. In 2003, Britney Spears and fellow pop star Christina Aguilera sang a rendition of Madonna’s “Like A Virgin” in bridal dresses at the MTV Video Music Awards. Madonna served as their groom in a tux and performed her latest single at the time, “Hollywood.” Mid-performance, Madonna kissed both Spears and Aguilera on the lips before final guest Missy Elliott came out. The unexpected, yet legendary, a moment caught millions of people’s attention around the world and was all anyone wanted to talk about for weeks. Shortly after, Madonna featured on Spears’ single “Me Against the Music” and starred in the music video.
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In 2006, it was reported their friendship had taken a hit when Spears revealed she was no longer interested in studying Kabbalah after Madonna introduced her to it. “Madonna spent months teaching Britney the Kabbalah system and splashed out thousands on the ancient scripture for her,” an inside source. As a result, it was rumored that Madonna ditched
Spears. The following year, Madonna appeared on “The Late Show with David Letterman” and reminisced over the time she brought a pair of her underwear to their interview. After recently being photographed wearing no underwear, Madonna threw shade at Spears and suggested David Letterman should consider giving Spears a pair.