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1 of 10
'Planes, Trains, and Automobiles' (1987)
Everything goes wrong in this ultimate nightmare of holiday travel. A diverted airplane leads to motel robbery followed by a burned-out rental car. Thanks to the masterful comedy of John Candy and Steve Martin, the characters' predicament is as hilarious as it is pathetic, but no one would wish it on their worst enemy.
2 of 10
Due Date (2010)
Take the Murphy's Law tragicomedy of Planes, Trains, and Automobiles, take away the holiday setting, transfer it from wintry Chicago to the southwestern desert, but cast similarly capable actors in the straight man/fool roles, and you'll still end up with an exercise in the ridiculousness of road trips. Next time your plane home gets delayed, just be grateful you didn't end up accidentally drinking the ashes of your companion's dead father.
3 of 10
National Lampoon's Vacation (1983)
The National Lampoon Vacation series has grown to more than six films (including the 2015 reboot starring Ed Helms) but it's still hard to top the original. Clark Griswold's desire to reach Walley World and recreate the vacation of his childhood leads to (among other things) a dirty campground, insane desert wanderings, a corrupt sheriff, and a dead aunt tied to the roof of the car. No other movie will ever make you so grateful to fly.
4 of 10
Are We There Yet? (2005)
It shouldn't be a surprise that a movie named after that most universal of road trip complaints should deliver on the schadenfreude. The last thing Nick Persons (Ice Cube) wants is little kids, but his crush on a divorced mother forces him to drive two mischief-makers across the country. Everything ultimately ends well, but the road to a happy ending involves lost luggage, multiple fistfights, and an exploded car navigator. There's a reason driving should always be the last option for important road trips.
5 of 10
Little Miss Sunshine (2006)
At least most of the other road trip movies on this list have the benefit of a working car. The Hoover family's Volkswagen, by contrast, is so broken-down it requires a running start, and once it gets started, it's impossible to stop it. Of all the mishaps of the family's journey to California for a beauty pageant (including a dead grandpa and a life-shattering color-blindness revelation) the funniest is that they still have to jump in their car while it's moving.
6 of 10
We're the Millers (2013)
Turns out even road trips with fake families can turn disastrous. David Clark's (Jason Sudeikis) plan to hire random strangers as his family in order to get drugs past U.S. border patrol quickly disintegrates into DEA run-ins, multiple standoffs, and worst of all, a spider bite in the worst possible place.
7 of 10
Compared to some of the other cross-country voyages on this list, Sideways' road trip is relatively innocuous (or is meant to be, at least): a bachelor party-like ride through wine country. Nevertheless, the two men (in star-making turns from Paul Giamatti and Thomas Haden Church) manage to screw up multiple relationships, destroy a car, and even break a nose.
8 of 10
Midnight Run (1988)
Anything that keeps characters from getting to their destination on a plane is usually the beginning of bad news. When embezzling accountant Jonathan Mardukas (Charles Grodin) fakes a panic attack on a plane, he and the bounty hunter escorting him (Robert DeNiro) are forced to take a train... followed, eventually, by stolen bicycles and borrowed cars, with a rival bounty hunter and evil henchmen in hot pursuit.
9 of 10
Harold and Kumar Go to White Castle (2004)
Every stoner's worst nightmare: a trip for munchies gone horribly wrong. All Harold and Kumar want is some White Castle sliders, but what they get instead ranges from accidental gunshot surgery to jail time to a high-on-ecstasy Neil Patrick Harris. Ultimately they do accomplish their mission... but it was never supposed to be nearly this hard.
10 of 10
The Three Burials of Melquiades Estrada (2005)
Tommy Lee Jones' directorial debut turns a disastrous road trip into the delivery of justice when Jones' character forces a border patrolman (Barry Pepper) to deliver the body of an immigrant boy he accidentally killed back to Mexico. It doesn't bode well for these characters as this trip is modeled after William Faulkner's As I Lay Dying, perhaps literature's worst road trip.