Madonna: Truth or Dare (1991)

This documentary chronicles Madonna's controversial 1990 "Blonde Ambition" international tour, kicking off in Japan during its rainy season, then traveling to North America with significant stops in Los Angeles, Detroit, Toronto, and New York. The film is a behind-the-scenes look at Madonna's relationships with her dancers and crew, her then-boyfriend Warren Beatty, and her family and friends, achieving an intimate glimpse into the boundary-pushing singer's drive and individuality.