22. Almost Famous (2000)
Director: Cameron Crowe
Stars: Patrick Fugit, Billy Crudup, Kate Hudson, Frances McDormand, Jason Lee
Bijou Phillips, Phillip Seymour Hoffman, Fairuza Balk, Anna Paquin, Zooey Deschanel
Vacation destination: All over the US, on tour with Stillwater
Touring with a band for an article in Rolling Stone, rubbing elbows with gorgeous groupies (Hudson, in a role that snagged her the Golden Globe for best supporting actress), and knee deep in the trenches of the rock lifestyle. It's safe to say William's (Fugit) summer vacation is better than yours will be. And to add insult to injury, he's still in high school.
Cameron Crowe's affecting tale of a teenager inadvertently thrust into an opportunity is not just envy inspiring fiction. William's vacation of a lifetime is actually a semi-autobiographical story based on Crowe's own experiences as a teenage writer for Rolling Stone, which explains why Almost Famous, despite seeming implausible, feels so genuine.