I don't care how gay viewers thought Legally Blonde was, this parable based on Little Red Riding Hood is both Reese Witherspoon's best and queerest film. It's nowhere near appropriate for kids, either, which makes for a perfect grown-up fairy tale. In it Witherspoon is a troubled teen with a sex worker mom (played by Amanda Plummer, who played queer in the cult classic Butterfly Kiss). When the girl tries to hitchhike to grandma's house she unwittingly gets picked up by a serial killer instead (the brilliantly bad Kiefer Sutherland as Bob), something that starts a long cat-and-mouse game that lasts until the stunning conclusion. Along the way, there's Brooke Shields, the late Brittany Murphy as lesbian heroin user Rhonda, and gay actor Guillermo Díaz as a gang member named Flaco.