Madonna: Truth or Dare (1991)

Right around the time that reality television was starting to develop on the small screen, pop icon Madonna appeared as herself on the big screen in Madonna: Truth or Dare (1991), not to be confused with the horror thriller Truth or Dare (2018). Even though this film is a documentary, the star was nominated for a Razzie Award for Worst Actress. Nevertheless, the movie was a huge success as it covers the sexpot’s Blond Ambition World Tour in 1990. Back then, Madonna and Warren Beatty were an item so, of course, he pops up in the flick. Other cameos by celebs include Antonio Banderas and Sandra Bernhard. Yet most of Madonna’s time is devoted to her show. When she’s not performing “Like a Virgin” (1984), “Like a Prayer” (1989) and “Express Yourself” (1989) on stage, she’s bantering behind the curtain with her backup dancers. Thanks to the direction of Alek Keshishian and Mark Miceli, we get to see Hubbard Street Dance Chicago alum Carlton Wilborn jump into the sack with Madonna. Did we mention he’s totally naked? As such, the ebony hunk shows off his abs, sack, and shaft. Can you dig it? If that’s not arousing enough, the skintastic stud makes out with fellow dancer Gabriel Trupin. In addition to exposing his chest, Gabe reveals his same-sex preferences! Mr. Trupin has since passed on but, like the rest of the cast, survives on celluloid via this pic. Also known as In Bed with Madonna, the title is a mouthful. Sweet dreams!