 A backdrop then started showing the newspaper reports on Madonna 's 1985 Playboy nude picture release . The backdrop moves up as Madonna appears , wearing a loose @-@ fitted black pant and top , with bejeweled glasses , for singing " Where 's the Party " . For " Into the Groove " Finch joins her on stage to dance alongside . Madonna then wore a pink bolero jacket which had the can of soup and the words " U " and " DANCE " flanking it . At the end she is joined by her backup singers and dancers . Together they take a bow to the audience and finish the performance . Next Madonna sang " La Isla Bonita " as a part of the encore , wearing the same red flamenco dress she had worn in the video . For " Who 's That Girl " , Madonna — flanked by Finch and a male dancer — strutted around the stage , asking the audience to join her on the chorus . Lastly , Madonna performed an energetic version of " Holiday " , signaling the celebratory and wholesome nature of the song 's theme . The song featured a new arrangement , with a guitar solo in the intermediate portion added by Leonard . She sang the final chorus twice , then asked the audience for a comb so that she could fix her hair and finished the performance , after taking a bow with her dancers to the audience . 
