The Top Ten Road Trip Movies of All Time

There’s no better way to get psyched for a road trip than to watch road trip movies! They may not accurately reflect your road trip experience (nor do you always want them to), but they always promise excitement – and excitement is practically guaranteed on the road as opposed to the sluggish boredom of airports and mass transit.

There are tons of lists of great road trip movies all over the web, but one thing that seems to be consistently wrong with many of the – lots of the movies listed don’t even have a vehicle involved! Great movies that capture the essence of road trips are those that detail the journey of two or more people (sometimes one), how they change as individuals, their adventures, the obstacles that they must overcome, and the role of the vehicle that they use to get there, whether it is a car, an RV, or a motorcycle.

The role of the vehicle in a road trip movie is essential – it becomes the character’s movable home and the setting for plot twists, showdowns, and personal transformations. Walking just isn’t the same.

When someone says “road trip” to you, do you imagine walking or driving?

See? That’s why wonderful movies like The Wizard of Oz have no place on a road trip movies list.

Another essential component in a great road trip movie is transformation or change – you want to see how the road trip molds the characters. That’s why movies like Dumb and Dumber and Road Trip won’t make it on this list – the characters really don’t change at all in those two movies (though they’re both well-loved funny movies). If you just want a bunch of laughs and no “meat”, I’ve listed the top silly/escapism road trip movies at the bottom of this list as an addendum. Who can’t use a few laughs?

Counting down from ten to number one, here are some of the greatest road trip movies of all time (clips included when available):

Number 10 – About Schmidt
Although this movie is officially called a comedy, it’s really more of a tragedy with some comedic moments. What makes it great is that recently widowed and retired Warren Schmidt’s (Jack Nicholson in a role where he doesn’t grin and caper for a change) road trip in the RV intended for his “golden years” with his late wife is one that helps him start to see himself and his life more clearly after living most of his life like an automaton. Talk about gaining perspective!

It’s also truly great because of the many realistic characters he meets on the road (love the couple who admire his RV and then end up kicking him out when Schmidt makes a pass at the wife) and the narrated letters to his sponsored African child, Ndugu, that relate his experiences and personal growth on the road. 
The Top Ten Road Trip Movies
Number 9 – Lost in America
Albert Brooks’ paean to 80’s yuppiedom set on a road trip across the U.S. hilariously captures the fantasy of “dropping out” of society and rambling in a motor home. The dream is to find themselves (couldn’t be more yuppie than that) while they “touch Indians, see the mountains and the prairies and all the rest of that song” – not a unique fantasy at all but one many have had when they’ve dream of the open road.

Watching this corporate couple’s precipitous decline as they gamble away all of their money in Vegas (the “breaking the nest egg” rant is classic) and end up scrambling for minimum wage jobs in a Podunk town just to keep afloat is highly entertaining. What makes it great is their whole new conception of the world (from cartoonish and one-dimensional to one that has much more to do with the real world) – that, my friends, is the essence of a truly great road trip movie.

Number 8 – Sideways
Road trips through California wine country will never be the same after you’ve watched Sideways. Middle age, career failure (Miles), commitment phobia (Jack), jealousy, wine snobbery (“I’m NOT drinking any *$!@# Merlot!”), and some serious emotional entanglements add up to a road trip movie that feels so real, you cringe and duck when helmets (Stephanie’s) start to fly!

Although this movie is set in beautiful vineyards gilded by the California sun and there’s plenty of talk of wine, it’s really not about wine at all. It’s about a journey of two men who end up being forced to face the brutal truths of their lives on a life-altering road trip. This is a road trip movie you can see over and over again, each viewing exposing new layers and nuances (a lot like a good wine!) 
Number 7 – It Happened One Night
Although they don’t have their own car, Clark Gable and Claudette Colbert ride in a bus and hitchhike their way down the road in this classic road trip movie.

This is a favorite for movie lovers due to both its clever humor and romantic story, but what makes it hit the top ten is the changes both characters go through on the road – Colbert’s character stepping outside of her privileged life and Gable’s character finding that his heart could trump his career aspirations. To top it off, this movie has the hitchhiking moment of all time when Colbert’s character shows Clark Gable how to guarantee that a car will stop (“I’ll stop a car, and I won’t use my thumb!”). 
Number 6 – Easy Rider
This low budget on-the-fly road trip movie classic may have some rough edges, but it also captures a grittier view of America and the hippie counter-culture perfectly. Like many road trip movies, this is an odyssey for each of the characters (Wyatt and Billy, played by the reportedly stoned Peter Fonda and Dennis Hopper) – the dream is to spread the word about personal freedom, not realizing in their naivete that they’d encounter more resentment and hatred than love.

This movie becomes even better when Jack Nicholson (as George Hanson, an alcoholic lawyer) raises his head from a cot in the next cell when the two main characters are in jail and proceeds to steal the show. Unlike Wyatt and Billy, George is an everyman and easier to identify with as the road trip continues on its way to Mardi Gras in New Orleans.

This is the kind of road trip most people don’t want to reenact – there are hookers, bigots, bad LSD trips, some undeserved jail time, and a tragic ending (not exactly what most people have in mind when planning a road trip) – but the spectacular scenery and kick-butt soundtrack manage to make it all appealing anyway.  
The Top Ten Road Trip Movies
Number 5 – Rain Man
This road trip movie is both hilarious and horribly sad at times – the kind of emotional swings that make it so real and believable. Although I’ve never been a huge fan of Tom Cruise, he plays the immature Charlie Babbit (who does a lot of growing up on this road trip with his hijacked suddenly-rich long-lost autistic brother, Raymond) to perfection.

This movie is really about Charlie’s inner journey as he overcomes his selfish childishness, accepts responsibility for his own behavior, and learns how to love someone other than himself.

Dustin Hoffman’s spectacular performance as Ray propels this movie even higher on this list of great road trip movies. Who can forget the Kmart underwear, the need to watch People’s Court (three minutes to Wapner), and “I’m an excellent driver”? Every stop along this cinematic road trip is outstanding.  
Number 4 – Planes, Trains & Automobiles
What a classic! From high hilarity to tear-jerking moments, this 80’s comedy classic has it all. Although much of this road trip is via mass transit, there are so many essential road trip movie moments in it that it is propelled higher on this list. Unlike most road trips that involve some dreamed-about destination, the coveted destination becomes home – and home for Thanksgiving at that.

The changes that Neal Page (Steve Martin) and Del Griffith (John Candy) go through as they’re slapped together again and again by fate are huge. Neal, that pressure cooker of a man, gets pushed to his limits by the obstacles along their route as well as by his traveling companion, Del – the antithesis of all the Neal is: happy-go-lucky, over-talkative, obnoxious, deeply kind and forgiving, and a slob. In the end, both become able to see life from the other’s perspective as well as gain insights about themselves.

This road trip movie has so many classic comedic moments – from “Those aren’t pillows!” to Neal’s f-word tirade at the rental car counter – but what takes this movie to the next level is the relationship that develops over the course of the trip between these two characters – the kind of bonding that only takes place on a road trip. \

Number 3 – Little Miss Sunshine
I had no idea how great this road trip movie was going to be, and boy, did it wow me! It’s frequently mentioned how dysfunctional the Hoover family is, but honestly, I thought they were more like real people I know than sick weirdos. Let’s face it – most families have a lot of skeletons in the closet (this family has several closets full!) This story of how a family in trouble makes it a mission for their plain and plump seven-year-old little girl to participate in a beauty pageant by crossing the country in a broken-down VW bus swings constantly between laughter and tears ( a lot how you’d feel if you were along for the ride).

In addition to each character’s inner journey (each has its own riveting story), the story of the journey itself puts it at number three. To start, what a vehicle! The VW bus isn’t just retro, it hardly runs. Watching the family pushing it to get it started and running alongside to jump in – do car problems get worse than that? Oh, yes, – then the horn starts acting up!

Then, as they make their way, each pit stop and problem along the way capture things we forget about road tripping: the easily overheard argument through motel walls, the mundane necessity of mini-marts, the conversations that escalate in the car. Despite everything, in the end, you’re sad the road trip is over and want to climb in the backseat of that VW bus for another ride.  
The Top Ten Road Trip Movies
Number 2 – Thelma & Louise
If this road trip movie came out a couple of weeks ago, I’d have it at number one – I was so in love with it and told everyone they had to see it. For a change, it was two women on a road trip rather than a bunch of guys or a family, something I’ve known to be far more common than movies would have you believe. My mother and her best friend, Irene, went on a road trip in the ’50s and camped their way across the U.S., seeing everything and having tons of adventures.

Now the adventures in this movie aren’t ones you’d want to repeat – a rape and a murder at a roadhouse that force the women to go on the run from the law and deeper into criminal activity – but there is nothing like watching the characters’ hopeful preparations and packing, the time they ride alongside a crop-dusting plane hooting and hollering, and the fantastic scenes in the desert to make you feel like you’re in that car, along for the ride of your life.

Of course, it doesn’t hurt that the vehicle of choice is a ’66 Thunderbird convertible, that Brad Pitt thrills as a hitchhiker they pick up in more ways than one, and that the leads are brilliantly played by Susan Sarandon and Geena Davis. Ultimately, though, it’s the dramatic personal transformations that make this movie truly great – Thelma grows up painfully and Louise faces a part of herself she walled off years before. Every time I see the ending, I’m always surprised. I had so much hope for them both, yet again.  
Number 1 – Vacation
Among road trip movies, Vacation is king. The Griswold family is utterly recognizable – you know these people: they’re your family. Their “quest for fun” at Wally World (Disney World in disguise, let’s face it) and their cross-country trip to get there is so classic, no other movie can compete. If you haven’t seen it, you’ve been living under a rock – climb out from under there and go watch it.

It’s impossible to pick the best moments in this road trip movie – every minute from beginning to end is the best! How do you choose? Check out the clip below for a few among hundreds…

The one character in this movie that changes is Clark. Endlessly optimistic, relentlessly hyper-planning every moment, he finally melts down in the end. This is the very thing I warn about in the dangers of overplanning. It’s a real problem to watch out for when planning a road trip!  
Want some silly and fun road trip movies (without the character development)? The best include The Blues Brothers, Road Trip, Dumb and Dumber, The Muppet Movie, and Smokey and the Bandit. No matter what type you choose, watching one is a must-do before a road trip (or even while on a trip if you’ve got a portable player) to really rev your engines!

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