16. Madonna: Truth or Dare (1991)
It’s Madonna Louise Ciccone’s sublime self-awareness that makes Truth or Dare such a kick. Knowing that everything she’d do in front of director Alek Keshishian’s cameras would be scrutinized by fans and critics alike, Madonna put on a show, obliterating the line between her private life and her public persona. She does a provocative bump-and-grind onstage, and then backstage fellates an Evian bottle in between explicit conversations about sex with her gay backup dancers. She lets Keshishian keep in her guarded boyfriend Warren Beatty’s criticism of her exhibitionism, and her own snide remarks about Kevin Costner and Oprah Winfrey. She has awkward encounters with old friends and family who remember her as a working-class kid from Detroit. The entire movie seems designed — by Madonna herself — to force the audience to question who “Madonna” is. The line between performance art and brand-building has never been so thin.
Source : Vulture