1. Paper Moon (Peter Bogdanovich, 1973)
To me a great road movie is one where the characters on the road encounter many other people, each pit stop a new vignette. Each one adding up to an overall emotional arc between the road trippers. Paper Moon does just that, over the course of their cons of various sizes, a bond forms between real-life father and daughter playing potential father and daughter.
2. Wild Strawberries (Ingmar Bergman, 1957)
Over the course of a drive, an old man encounters all aspects of his past whether in the form of people met along the way or through his dreams, in which he looks back on episodes from his youth as if he were a ghost, witnessing from afar.
3. Locke (Steven Knight, 2013)
Unlike the other films mentioned this is not a picaresque film. Locke has a clear destination and everyone he talks to on the phone can be divided between those who urge him to come back home or push him further to where he’s going.
4. Wages of Fear (Henri-Georges Clouzot, 1953)
The element of fun during a road trip is ruined when at any moment you could blow up, but because of that, the unpredictability factor still remains.
5. Dumb and Dumber (Farrelly Bros, 1994)
After the unnecessary sequel, the stupid humor of this movie comes off as extremely subtle. For an example look at the 7:45 scene; they come off as dumb and not retarded maniacs. Plus Harland Williams is missing from the sequel.
6. 9 Souls (Toshiaki Toyoda, 2003)
What starts out as a fun road trip where nine escaped convicts get as far from prison as possible, it soon turns into a highly emotional journey by the halfway point when we realize that these guys don’t just want to drive aimlessly for the rest of their lives but find somewhere that they belong. A deeply rewarding experience.
7. Inside Llewyn Davis (Coen Bros., 2013)
An extended section of this collection of episodes (that is anything but wandering picaresque) is a road trip. Our folk singer protagonist embarks on trip from New York to Chicago with a quiet poet (Garrett Hedlund) and a jazz musician (yet another great John Goodman performance in a Coen film). While on the road Llewyn is given opportunities to curb his self-destruction and even one to save a cat. Thankfully, the Coens stay true to the character they’ve created and feel no need to redeem him just because a screenwriting book says so.
Runners-up: Something Wild, Stagecoach, Red River, The Trip, Wild at Heart, and Zombieland.
There is also a Korean film called Road Movie (2002) which could conquer this list.