The Coen Brothers took Homer’s The Odyssey and threw it into the deep south during the Great Depression. It’s the strangest, most beautiful road trip movie of the year.
The year was a strange, liminal moment in cinema. The 90s were dead, Y2K hadn’t killed us, and Hollywood was figuring out what the new decade looked like. The result? An absolute gold rush of road trip movies.
Most people forget this is a road trip movie. Written and directed by Christopher McQuarrie ( The Usual Suspects , Mission: Impossible ), The Way of the Gun follows two drifters (Ryan Phillippe and Benicio Del Toro) who kidnap a pregnant surrogate mother.
Whether you need a comedy, a thriller, or a spiritual awakening, 2000 had a car, a tank of gas, and a broken-down radiator waiting for you.
Ulysses Everett McGill (George Clooney), Pete, and Delmar—three escaped convicts chained together, searching for buried treasure.
When you think of road trip movies, you probably picture 60s hippies in a psychedelic bus or John Candy and Steve Martin trading barbs in Planes, Trains and Automobiles . But let’s fast-forward to the turn of the century.
Once they snatch the girl, they spend the entire second act driving through the Mexican desert, trying to get to a seedy clinic while a fixer (James Caan) hunts them down.
The set pieces are legendary. The snake in the dorm room. The blind guy driving the car. The cow scene (you know the one). Tom Green steals the show as Barry, the chaotic wildcard. It’s gross, it’s inappropriate, and it holds up as a perfect snapshot of pre-9/11 optimism.
