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The majority of the film is in black and white, while the concerts were shot in color. The title of the film is taken from a scene of "truth or dare" that Madonna plays with her entourage of dancers and backup singers in which she reveals a very personal feeling of hers that she originally refused to allow in the film. The director said that Madonna would have to kill him in order to cut that one scene... so the scene was left in.
I found it interesting to see what happens the moment Madonna steps off stage--what goes on between shows or even songs. When technical problems occur during the show, she makes it known (in a not-so-subtle way) to her technical directors.
You get a glimpse of what kind of relationships Madonna leads and the roles that she plays in them. You meet her dad and brother, and see what sort of relationship they have as a family. For the most part, however, her tour family is made up of her dancers and backup singers.
You probably haven't seen this side of Madonna before, and you probably never will again. It's just a brief slice of her life.