 " True Blue " had two music videos to accompany it . Shot in early September 1986 in New York , Madonna 's own video for the song was directed by James <unk> , who worked with Madonna in her videos for " Live to Tell " and " Papa Don 't <unk> " , produced by Robert <unk> and David <unk> with photography by Michael <unk> . The <unk> version features Madonna with three dancers and a 1950s car in an all @-@ blue <unk> . Madonna changes her hairstyle from short @-@ cropped in " Papa Don 't <unk> " to a bushy platinum blonde <unk> and sings the song in choreographed moves backed by her dancers . It displays a flashing back to fifties rock 'n'roll youth culture . 
