16. The Wackness (2008)
Director: Jonathan Levine
Stars: Ben Kingsley, Josh Peck, Famke Janssen, Olivia Thirlby, Mary Kate Olsen, Method Man
Vacation destination: Fire Island
For Luke (Peck), a single summer for shirking responsibility remains after high school graduation, a terrifying concept that leads his friends to flee Manhattan for their final getaway before college begins, and leaves Luke alone in Manhattan. It wouldn't be a vacation if he actually works, so rather than tainting his time off, Luke sells pot to make ends meet and finds his best client in his therapist (Kingsley).
Lame attempts at slang aside, The Wackness is a surprisingly affecting story about how Luke and his therapist connect on a trip to Fire Island, where they find their shared failures in love (Luke with the shrink's daughter, and the shrink with his wife) and a little marijuana, and a few good mixtapes help them connect, despite doc not being natural with modern-day slang.