To start marketing '' American Life '' , Madonna performed the American Life Promo Tour . A performance on Tower 's Fourth Street in Manhattan was presented to around 400 people and featured acoustic performances of " American Life " , " Mother and Father " , and " Hollywood " . On August 27 , 2003 , Madonna opened the MTV Video Music Awards performing a medley of " Like a Virgin " and " Hollywood " with Britney Spears , Christina Aguilera , and Missy Elliott . The performance started with Madonna 's daughter Lourdes walking on stage with another girl , dressed as flower girls at a wedding . Spears appeared on stage atop of a giant wedding cake , 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 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 whole performance was a tribute to Madonna and an homage to her performance of " Like a Virgin " at the awards ' inaugural show in 1984
inaugural show
1984 MTV Video Music Awards
Hollywood (Madonna song)