Longshot is a 2000 teen film directed by Lionel C. Martin, and written by Lou Pearlman, as a promotional tool to promote the acting debuts of his succession of successful boybands and girl groups, such as NSYNC, O-Town and Natural, as well as rapper Lil' Kim, singer Britney Spears, girlband Innosense and boyband LFO, all of whom had cameo appearances in the film, as Pearlman had worked with all of them during the late 1990s and early 2000s. The plot recounts the tale of a young boy, Alex Taylor, who gets caught up in his brother's activities as a gigolo, and uses each of the said pop acts as a tool within the film.
The film was never released to theaters in America, instead being shown on the Disney Channel as a television movie, and later being released on video and DVD as a home entertainment release. However, it was released to theaters in Germany, where all of Pearlman's boybands had enjoyed success long before their international debuts, and was also released on DVD in the Netherlands. The film was also packaged with copies of Crossroads, a film which starred Britney Spears, in selected FYE stores in the United States.
About one-third of the film was service-produced in Toronto, which doubled up as New York City within the film, under contract with The Danforth Studios Ltd, a subsidiary of SpaceWorks Entertainment Inc. The film was a complete commercial failure, taking in nowhere near the $20 million it cost to film at the box office. The film was also panned by critics, who claimed that many of the pop acts who appeared in the film later claimed to have only appeared due to the amount of pay they would receive for a cameo appearance.