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16 Memorable Road Trip Movies8

By Steven Novak

Everyone loves a good road trip. There are few better ways to see the world than to hop in a car, throw a few bags in the back, put on your favorite tunes and go where the road takes you. It’s as American as baseball, apple pie and big screen TVs. That’s probably why Hollywood loves the idea of the road trip and has dedicated so many movies to the subject. Take a gander at this list of 16 great road trip movies and get in the mood to hit the road.

1. The Muppet Movie – 1979

For me personally, road trip films just don’t get any better than The Muppet Movie. While relaxing in a swamp and strumming on his banjo, Kermit the Frog is approached by Dom DeLuise and is told he has talent. Minutes later, our favorite green felt frog is on a cross-country trip to Hollywood – because if you can’t trust Dom DeLuise’s judgment, then whose? In any case, the adventures are vast, the characters memorable, and the landscape varied. In the end, there’s a Studebaker, Orson Welles, a movie deal, and it all culminates with one of the greatest songs in the history of cinema, “The Rainbow Connection.”

2. Planes, Trains, and Automobiles – 1987
When it comes to road trips and hilarity, they don’t get much better than John Hughes’ too often overlooked Planes, Trains, and Automobiles. Steve Martin plays a tightly wound ad executive trying to get home to his family in Chicago before Thanksgiving. Things go horribly, horribly wrong, and he ends up having to take the journey with an overly boisterous nice guy played by John Candy. Along the way, a car gets burnt to a crisp, Steve Martin’s hand gets wedged between Candy’s butt cheeks, and the bond between the men strengthens further than they could have ever imagined. (Putting your hand between the flesh pillows of another man’s crack tends to do that.)

3. National Lampoon’s Vacation – 1983

The best Chevy Chase vacation movie has always been, and always will be, the first. Though his wife would rather have flown, Clark Griswold insists that his family take the car and see the country on their way to America’s favorite family fun park, Wally World. Very quickly things begin going horribly awry. Their car careens off a highway, they’re forced to visit Uncle Eddie (who has a daughter that claims her daddy thinks she’s “the best at French kissing”), an old lady eats a pee-soaked sandwich, and of course someone dies. Clark does get to go skinny-dipping with Christie Brinkley though – that has be worth at least some of his troubles, right?

4. The Wizard of Oz – 1939

Though there isn’t a single car involved in this film, there is an awful lot of traveling and a heck of a lot of road – the Yellow Brick Road to be exact. Dorothy Gale, a twelve year-old Kansas farm girl, is knocked unconscious during a tornado and wakes up to a smashed witch and a bunch of munchkins. She is then told she needs to travel to Emerald City to see the Wizard of Oz if she wants to get home. She picks up a couple of hitchhikers along the way and off she goes. The film’s a classic. Plus it has flying monkeys, and flying monkeys are cool.

5. Sideways – 2004

Directed by Alexander Payne and adapted from a 2004 novel by Rex Pickett, Sideways is the story of a couple of forty-something men, played by Thomas Haden Church and Paul Giamatti, who decide to take a week-long road trip to the wine country of Santa Barbara in honor of Haden Church’s impending marriage. It doesn’t take long for Giamatti to discover that his pal has little interest in wine and far more in dipping his wick – which is the euphemism I’ve chosen for sex and I’m sticking with it. Part comedy, part drama, Sideways is a successful piece of work on a number of levels and a quality road trip flick to boot.

6. The Darjeeling Limited – 2007

As the most recent addition to our list, Wes Anderson’s The Darjeeling Limited is a pretty fantastic piece of work. The film tells the story of three brothers, played by Owen Wilson, Adrien Brody, and Jason Schwartzman, that haven’t seen each other since their father’s funeral a year prior. The trio plans a trip through India that will culminate with them reuniting with their long lost mother. It’s funny, it’s poignant, and it’s set against the breathtakingly beautiful backdrop of India.

7. Death Race 2000 – 1975

When some people think of road trip movies they instantly think of Burt Reynolds in The Cannonball Run. My thought is, if I’m going to add a “race” movie to the list, it’s going to be the one where innocent bystanders get smashed for points rather than the one starring Dom DeLuise. Maybe that’s just me though? Death Race 2000 is a little gem from the 70’s about a future United States that’s been destroyed by a financial crisis and has fallen in love with a transcontinental road race that involves running over innocent people for points. Ignore the crappy sequel made in 2008. As far as I’m concerned, this is the only Death Race worth watching.

8. O Brother, Where Art Thou? – 2000

Loosely based on Homer’s The Odyssey (which really is the “OG” of road trip stories), The Coen Brother’s O Brother Where Art Thou? is a film about a trio of chain gang escapees that set out to retrieve 1.2 million dollars in buried treasure that one of them claims to have stolen from an armored car before his incarceration. They end up making a record as “The Soggy Bottom Boys” for some extra money, and it becomes pretty famous with the locals. They have a run-in with three seducing sirens, go head-to-head with a Klu Klux Klan lynch mob, and are saved from death by hanging thanks to a flood. At their most basic, road trip flicks are more about the journey than any actual road anyway, and there’s a heck of a journey going on here.

9. Pee-Wee’s Big Adventure – 1985

Paul Ruben’s bizarre character from television (Pee-Wee Herman) made his big screen debut in this equally bizarre little film that was directed by a bizarre up and coming director named Tim Burton – and that’s a whole lot of bizarre. After Pee-Wee’s bike is stolen by his portly neighbor Francis, the gray-suited man-child sets off on a cross-country adventure to retrieve it. Along the way, he meets a fugitive that made the mistake of cutting the “Do Not Remove Under Penalty of Law” label from a mattress, performs for a bunch of bikers, interrupts a Twisted Sister video shoot, gets the girl, and ends up as the subject of a movie made about his life. The only person he doesn’t encounter is Cowboy Curtis – which is a bit of a downer.

10. Easy Rider – 1969

I’m going to be perfectly honest. I’m not the hugest fan of the Dennis Hopper, Peter Fonda bit of 1960’s cultural exploration that is Easy Rider. Don’t get me wrong. It’s a good flick. It’s just not a great flick. That being said, I readily acknowledge that fact that it is almost impossible to write a respectable article about road trip movies and not mention it at some point. At it’s most basic, the story is fairly simple: a couple of bikers set out to travel the American Southwest with the aim of achieving freedom. They meet up with ACLU lawyer/drunk played by Jack Nicholson, get in fights with the locals, meet some prostitutes, take in the Mardi Gras celebration, and do a lot of drugs. Movies don’t get much more “60’s” than Easy Rider.

11. It Happened One Night – 1934

It Happened One Night holds the distinction of being the oldest movie to make our little list – beating out The Wizard of Oz by just a few years. Directed by legendary auteur Frank Capra, the film tells the story of a pampered socialite played by Claudette Colbert, who attempts to get out from underneath her father’s thumb and ends up falling in love with a roguish reporter played by Clark Gable. Despite the fact that the film is almost eighty years old, the comedy still works for the most part (which isn’t too often the case), and Gable and Colbert have more chemistry than Brangelina.

12. Midnight Run – 1988

In Midnight Run, Robert De Niro plays a disgruntled former cop turned bounty hunter (Jack Walsh) whose been hired to retrieve an accountant, played by Charles Grodin, who embezzled 15 million from gangster Jimmy Serrano. He has two days to capture him and bring him in. The task proves to be far more difficult than he imagined, and of course, wacky hijinks ensue. Soon Jack is posing as an FBI agent named Alonzo Mosely while dodging the cops, the mob and a rival bounty hunter with a beard so sharp it could cut glass – all the while coming to terms with the fact that the guy he’s been hired to retrieve really isn’t that bad a guy after all.

13. Little Miss Sunshine – 2006

Directed by the husband and wife team of Jonathan Dayton and Valerie Faris, Little Miss Sunshine is the story of a screwed up family that becomes solely focused on getting their youngest member, Olive, to the “Little Miss Sunshine” beauty pageant in Redondo Beach, California. They have two days, little money, and a beat up yellow Volkswagen Microbus to get them there. Along the way, they’re forced to face family issues head on, someone dies, and little Olive’s dance routine to Rick James’ “Superfreak” proves to be the scandal that horrifies the beauty pageant world. As road trip movies go, Little Miss Sunshine hits almost every note and is among the best.

14. Fear and Loathing in Las Vegas – 1998

Based on the novel by Hunter S. Thompson, and directed by Terry Gilliam, Fear and Loathing in Las Vegas is the bizarre-beyond-words, semi-autobiographical story of a road trip to Vegas taken by of a writer aptly named Dr. Gonzo and his lawyer Raoul Duke. The movie works on two levels. One: it’s an actual, physical road trip to sin city taken by two guys in a car. Two: the copious amount of drugs consumed by the lead characters take them on a road trip to places roads don’t generally go. Unless of course there’s a Mescaline Highway out there somewhere where giant bats attack anyone driving it. I’ll have to consult my Thomas Guide on that one.

15. It’s a Mad Mad Mad Mad World – 1963

At the time of its release, this 1963 comedy directed by Stanley Kramer was intended to be the absolute greatest of road trip movies ever made. Did it succeed? Not really. Is it better than the less than stellar reputation it’s garnered over the years? Of course. The ensemble cast is a who’s who of old Hollywood and includes Mickey Rooney, Sid Caesar, Buddy Hackett, Jonathan Winters, Spencer Tracy, Ethel Merman, Milton Berle, not to mention host of others, all of which are racing for a mysterious $350,000 hidden under a “big W.” If that seems like a lot of trouble, keep in mind $350,000 was a lot more money in 1963.

16. Duel – 1971

Okay, so Steven Spielberg’s first feature film (which was also made for television) isn’t “exactly” a road trip movie in the traditional sense of the term. It does, however, feature a whole lot of roads and enough cars driving on them that it might make your average NASCAR fan say, “enough with the driving already.” The story is simple: a massive rusty truck terrorizes a salesman on a business trip. That’s pretty much it. Despite the simplicity of the plot, it’s made extremely well. The action is good, the tension is solid, and lots of stuff gets smashed. Smashing stuff is good. Real good.

Steven Novak is a writer, illustrator, graphic designer and admitted lifelong nerd with an embarrassingly large DVD collection. He is currently working and living in the Southern California desert. His most recent fantasy/action adventure novel, “Forts: Fathers and Sons,” is available everywhere books are sold.

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