Madonna: Truth or Dare interviews that she hates the title of "In Bed with Madonna". The original working title of the documentary was ""Truth or Dare: On the Road, Behind the Scenes and In Bed with Madonna"". During the summer of 1990, Madonna hired director Alek Keshishian to film backstage and onstage footage of her Blond Ambition World Tour. The entire documentary is filmed in black-and-white, except for onstage sequences which are in full color. There are appearances from celebrities such as Al Pacino, Mandy Patinkin, Olivia Newton-John, Antonio Banderas, Sandra Bernhard, Kevin Costner, and Warren Beatty, whom she was dating at the time.
Holly Cunningham man in and apologize, finding out his name is Wes and that he coincidentally already knows Jade. Wes forgives them, but when Wes and Holly are alone, Wes acts violent towards her. Holly tells Callum about this although Callum refuses to believe it, causing them to argue. During a house party on the trip, Wes joins Holly alone in the bedroom and forces her to let him take topless pictures of her or he will report her to the police for nearly shooting him. He is then interrupted by Theresa, who is also at the party, and Wes then leaves.