In "Ciao, Italia! Live from Italy" Madonna visits the land of her noble heritage for this high-energy concert video filmed in 1987. It contained footage from a previous TV special of the Who's That Girl World Tour, Madonna in Concerto, broadcast in Europe in 1987, filmed at the Stadio Comunale in Turin, Italy. The video release also contained footage from shows recorded in Florence, Italy and Tokyo, Japan. The tour supported her 1986 third studio album True Blue, as well as the 1987 soundtrack Who's That Girl.

Film geek Josh is looking for the subject of his new documentary when a chance meeting puts the perfect star in his sights—Dylan, his school's most popular junior. But Dylan's hopes of using the film to become Blossom Queen don't quite match with Josh's goal to make a hard-hitting exposé about popularity. Will Josh shoot the film as planned, or show Dylan as the truly interesting person she is?