I'm resisting the urge to just list my 5 favorite movies that could possibly be classified as a "road trip" movie. For example, I hesitate on Blues Brothers because it doesn't feel like "road trip" to me. It's entirely set in the Chicagoland area. I'm trying to focus on ones that really scream "road trip" to me:
1. Midnight Run
2. Leningrad Cowboys Go America
3. O Brother, Where Art Thou?
4. Lost in America
5. Wild Strawberries