The medley track " Like a Virgin/Hollywood " was performed during the opening of the 2003 MTV Video Music Awards on August 27 , 2003 , where Madonna was joined by Britney Spears , Christina Aguilera , and Missy Elliott . The performance started with Spears appearing on stage on top of a giant wedding cake while wearing a wedding gown and veil ; she sang the first few lines of " Like a Virgin " before Aguilera appeared from behind the cake and joined her . Madonna then emerged from the cake wearing a black coat and a hat and started singing " Hollywood " before proceeding to kiss Spears and Aguilera on the lips . Missy Elliott came out from a wedding chapel to sing her song " Work It " halfway through the performance . The kiss generated strong reaction from the media . Feminist author Camille Paglia described the moment as great ; she noted that the kiss was like Madonna saying to Spears , " I 'm passing the torch to you . " However , according to her , Spears could not take advantage of the kiss as later her career and lifestyle came under immense media scrutiny and criticism . Paglia said that " literally from that kiss , from that moment onward , Britney has spiraled out of control . It 's like Madonna gave her the kiss of death ! " Madonna commented on the kiss ; " I am the mommy pop star and she is the baby pop star . And I am kissing her to pass my energy on to her . " This performance was listed by '' Blender '' magazine as one of the twenty-five sexiest music moments on television history . MTV listed the performance as the number-one opening moments in the history of MTV Video Music Awards
2003 MTV Video Music Awards
2003 MTV Video Music Awards
Remixed & Revisited