Also known as Whiteboyz, the 1999 film by director Marc Levin follows a group of wanna-be white rappers from Iowa as they venture into the ghetto of Chicago looking for drugs. Think Vanilla Ice as a midwestern high school student trying to act like gangstas. As ridiculous as the film’s premise is, it gets fairly intense towards the end as the kids from the corn fields realize they are in way over their heads.

Shot on location in Iowa City and Davenport, Iowa, as well as Cabrini Green, the film includes cameos by several top rap stars, including Dr. Dre and Snoop Doggy Dog. They must have owed someone a big favor.

The film helped launched the career of actress Piper Perabo, who went on to star in Coyote Ugly.