The Sure Thing
My favorite road movie is the very 1980s The Sure Thing, starring John Cusack as Walter "Gib" Gibson, a college student spending his winter break traveling across the country to meet a girl who "loves sex" and is the titular "sure thing." His journey to no-strings-attached sex is complicated by Allison, a classmate and Gib's English tutor, who ends up in the same carpool, also headed to Los Angeles to visit her boyfriend. Their constant bickering gets them kicked out of the car, but they eventually make their way to L.A. Once they get there, of course, they realize they've fallen in love with each other in true 1980s movie fashion. This movie certainly isn't high art, but it's one of the more entertaining '80s teen movies, and it was directed by Rob Reiner, who would go on to direct The Princess Bride two years later. Gib and Allison's mishaps on the road are exactly what you would expect to happen to a pair of bickering college students stranded somewhere in the middle of a cross-country trip and there is some particularly inspired dialogue along the way. It may not make any overarching statements about the human condition, but it is entertaining enough to merit multiple viewings.