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15 Greatest Road Trip Movies You’ll Want To See

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15 Greatest Road Trip Movies You’ll Want To See

The road trip movie is a time-tested plot formula frequently used by Hollywood because it presents ample opportunity for story structure, character development, and wacky situations. In all of these movies, you can almost guarantee that you’re going to watch some characters embark on a cross-country adventure by planes, trains, and automobiles. On their travels, they will have some profound epiphany about their approach to life, or their relationship will develop from indifference or dislike to gradually becoming best friends. Perhaps they will come to a realization about their commitment to work over family. They are usually brought to this realization by the lengths they have to go to in order to reach their destination – the difficulties they face make them wonder why they’re bothering so much in the first place. Unfortunately, when it comes to a genre that’s been done to death and is riddled with clichés, stereotypes, and tropes, it’s pretty hard to weed out the good ones. So, without further ado, here are fifteen road trip movies that transcend the clichés and subvert the tropes to become truly inspired, original, and entertaining pieces of cinema.

15. Sideways

Sideways is a comedy movie about a bachelor party. In it two guys, one of whom is about to get married, spend a week driving through wine country, sampling vino. Upon a passing glance, you might dismiss this as a ‘tame Hangover’ or an ‘arthouse Hangover’, but with topics spanning from depression to alcoholism, and from extramarital affairs to stealing from one’s own mother, The Hangover is more like a ‘tame Sideways.’ This movie is the perfect example of using a road trip story format to send characters on a reflective, personal journey that alters their lives indefinitely. Sideways was a phenomenal success upon it’s release grossing over $100 million. It won an Academy Award for Best Adapted Screenplay, and the characters’ negative comments about merlot reportedly cost the merlot industry about $400 million.

14. Smokey and the Bandit

“East bound and down, loaded up and truckin’! We’re gonna do what they say can’t be done! We’ve got a long way to go and a short time to get there…” Who doesn’t remember Smokey and the Bandit? It’s a campy, bubblegummy popcorn car chase movie, but it’s damn entertaining. Earning $300 million, Smokey and the Bandit was the second highest grossing movie of 1977, behind a little-known sci-fi flick called Star Wars. No one could forget Jackie Gleason’s performance as Sheriff Buford T. Justice (“Smokey”) or especially Burt Reynolds’ charming turn as Bo Darville (“the Bandit”) in a riotous cat-and-mouse action comedy described by Leonard Maltin as “about as subtle as The Three Stooges, but a classic compared to the…countless rip-offs which followed.” And who doesn’t watch Smokey and the Bandit and immediately want to hop in a Trans Am and storm across the highways of America to the sound of “East Bound and Down?”

13. Borat

Borat, also known by its full title Borat: Cultural Learnings of America for Make Benefit Glorious Nation of Kazakhstan, is a road trip movie presented in a mockumentary format. But it wasn’t made in the same way that other mockumentaries like The Office were made, because with those movies and shows, everyone involved knows it’s not a real documentary. With Borat, pretty much only Sacha Baron Cohen (who played Borat) and the guy holding the camera knew it was fake. They wanted to get authentic reactions from their subjects, so they basically did make a real documentary about a fictional guy. So, Baron Cohen really did go into a Confederate antique store and clumsily break everything in there. And he really did get a driving lesson and tell his instructor some misguided information about sexual consent. And he really did go into a Pamela Anderson book signing and try to kidnap her (Anderson was in on it – but her bodyguards weren’t!). That takes balls! People called the police on Sacha Baron Cohen a reported 92 times during the production of the movie. The FBI assigned a special team to follow him after there were various reports of a mysterious Middle Eastern man driving an ice cream truck across America. But the rewards are obvious, based on the hilarity of the final product and that’s why this one stands out from the crowd.

12. Nebraska

Alexander Payne’s Nebraska is both sad and funny, and shot on anamorphic lenses in crisp black and white; it’s an utterly beautiful film. The movie has such a simple premise: Bruce Dern plays Woody, a grumpy old man in Montana who believes he’s won a million dollars and will stop at nothing to claim it in Nebraska. His determination forces his son, played by SNL’s Will Forte, to drive him there. It’s not about the million dollar prize of course; it’s a story about father-son bonding. According to The Daily Telegraph’s positive review of the film, it’s about even more than that. They describe it as “a bittersweet elegy for the American extended family, shot in a crisp black and white that chimes neatly with the film’s concern for times long past.” Fun fact: Better Call Saul pays tribute to this movie at the beginning of every season. Saul star Bob Odenkirk features in Nebraska, and in the story of Better Call Saul, he’s now living in Nebraska under the name Gene. Whenever this part of his life is featured on the show, it’s shot in black and white.

11. Natural Born Killers

It’s fair to say that Natural Born Killers is a pretty messed-up piece of cinema. What else do you expect from an early Quentin Tarantino script? He went really balls to the wall with this one, and Oliver Stone’s direction of it is – in typical Oliver Stone fashion – fascinatingly horrific. The movie is satirical in its excessive use of graphic violence and gore (imagine Tarantino gore times Stone gore squared). It’s also satirical in its sensationalization of a pair of mass murderers who also happen to be lovers a la Bonnie and Clyde. It presents a scene of family home life starring Rodney Dangerfield as a situation comedy with a laught track, except it’s not as funny as you’d expect from a family sitcom starring Rodney Dangerfield. That format and casting is just a red herring to lull you into a false sense of familiarity – then Tarantino and Stone pounce with their depictions of sexual perversion and domestic violence (all with studio audience laughter set behind it). Entertainment Weekly named it the eighth most controversial film in history, but at its core, it really is a love story about two people who find each other, fall madly in love, and hit the open road. It’s inspiring, in a very broad way.

10. Paper Moon

Although released in 1973 during the New Hollywood era of filmmaking and shot in black and white, Paper Moon is a movie for the ages. It’s timeless; it would be just as relevant and affecting to audiences today as it was back then, when it made more than ten times its initial budget. First off, it’s directed by Peter Bogdanovich and it was made in the ‘70s, so it’s pretty much bound to be good. Bogdanovich directed the coming of age masterpiece The Last Picture Show and his contemporaries and peers were the likes of William Friedkin, Brian De Palma, Martin Scorsese, and Michael Cimino. So yeah, he knows a thing or two about throwing together a movie. Second, the story is a beautiful tale of father-daughter bonding (parental bonding appears to be a common theme amongst road trip movies), starring real-life father and daughter, Ryan and Tatum O’Neal. It’s set in the Great Depression and follows a con man who gets stuck with a young girl who is potentially his daughter and they become the best of friends. If you haven’t seen it, I suggest you do so right now.

9. Fear and Loathing in Las Vegas

Have you ever wanted to take an acid-fueled road trip across the Nevada desert with Johnny Depp and Benicio Del Toro? Who hasn’t! Well, with Fear and Loathing in Las Vegas, you can! Monty Python’s Terry Gilliam took gonzo journalist Hunter S. Thompson’s book, which was previously thought to be unadaptable because it’s basically the ramblings of a drug-addled madman, and pretty much translated his drivel onto the screen. It’s astounding. It feels like an actual acid trip, and that’s exactly what Gilliam wanted to achieve. He accomplished what even the likes of Martin Scorsese and Oliver Stone failed to – he adapted Fear and Loathing in Las Vegas for the screen. And when it comes to Depp’s performance, you can’t really find more commitment from an actor. He developed a close personal relationship with Thompson before playing him; he borrowed Thompson’s actual clothes to wear in the film and let Thompson himself shave his head to replicate his own balding head.

8. Little Miss Sunshine

There’s something warm and comfortable about the experience of watching Little Miss Sunshine; how it’s undercut with a tragic melancholy that makes the film a totally unique beast. Steve Carell plays Frank, a gay Proust scholar who has just attempted suicide before the events of the film. Frank is about as far removed from Michael Scott as a character could be, but Carell plays his attempts at optimism despite his depression beautifully. That’s just one example – the characters are all brilliantly fleshed out and real, and we’re happy to watch them on this journey in a van that they have push to get it going every single time. Michael Arndt, the first-time screenwriter who won an Oscar for Little Miss Sunshine , who would go on to write Toy Story 3, summed up the plot of his own script perfectly: “You start off with all these people living their separate lives and the climax of the movie is them all jumping up onstage together. So the story is really about this family’s starting separately and ending together.” If you have a friend who is unsure what the comedy-drama genre entails exactly, show them Little Miss Sunshine, because it’s a movie that simultaneously pulls off both perfectly.

7. The Last Detail

The Last Detail is everything a movie should be. Its director, Hal Ashby, was an expert in taking a simplistic premise and turning it into a masterpiece. He took the idea of a teenage boy and an old lady dating and turned it into a love story for the ages (Harold and Maude). His Vietnam War movie (Coming Home) wasn’t about the war at all – it was about a woman whose husband is fighting in the war who falls in love with an injured vet. But The Last Detail is his crowning achievement: the story of two Navy officers tasked with taking a disgraced comrade to prison and showing him the time of his life on the way (sort of a last hoorah). During production, the studio asked Robert Towne, the writer of The Last Detail, to tone down the use of swear words, but that’s the whole point! Towne told the studio, “This is the way people talk when they’re powerless to act; they bitch.” Time’s review summed up the solemn beauty of this movie perfectly: “There is an unpretentious realism in Towne’s script, and director Ashby handles his camera with a simplicity reminiscent of the way American directors treated lower-depths material in the ‘30s.”

6. National Lampoon’s Vacation

National Lampoon’s Vacation represents everything a comedy movie should be. It starts out with a relatable premise: a middle class dad wants to take his family on the perfect vacation, and they simply roll their eyes at every one of his attempts at fun. And then it backs it up with a steady stream of hilarious gags: falling asleep at the wheel, getting ripped off after taking a wrong turn in an urban neighborhood, taking a detour and crashing the car in the middle of the desert etc. Chevy Chase plays Clark Griswold in a brilliant, bumbling way that holds a mirror up to every suburban father in the audience. And, it’s that relatability that has elevated a great comedy to classic status. We’ve all tried to drive to Walley World at some point or other in our lives, and we’ve all faced frustrating setbacks (if not as entertainingly catastrophic as the Griswold clan). So, when Clark loses it, we feel his pain and feel comfortable laughing at it.

5. Easy Rider

Easy Rider rode into cinemas on a Harley-Davidson in 1969. It’s generally believed that only people can take drugs, but that belief can be tested with Easy Rider; a film that appears to be all hopped up on coke, acid, and adrenaline. Using real drugs in the movie, Dennis Hopper made a counterculture biker movie about two bikers who sell a boatload of cocaine and then take off through the deserts of the United States that completely changed the industry for a whole decade. According to Peter Biskind’s book Easy Riders, Raging Bulls, it was Easy Rider that paved the way for the New Hollywood era of cinematic history that ran through the 1970s and gave us Taxi Driver, The Godfather, Apocalypse Now, The Graduate, and many more. It’s been called a “touchstone for a generation,” which “captured the national imagination.” The movie encapsulates the heart of the American dream and the tragic pitfalls that can come along with it.

4. Dumb and Dumber

Dumb and Dumber could’ve just been – as suggested by its title (twice) – another dumb comedy. But it’s not in the slightest. It achieves the rare, extraordinary feat of being crude and filled with slapstick humor while still being a smart and sophisticated comedy. The Farrelly brothers’ work is generally characterized by its toilet humor and blunt comedy, but the content of their screenplays is always so considered and inspired. They’re hard workers. Dumb and Dumber is riotously funny; it’s not coarse and it doesn’t use offensive language or easy targets for cheap laughs. Jim Carrey’s delivery of every line is so on point and perfect that it becomes seared in the viewer’s memory. The gags are all so hysterical, from the dead parakeet to the harmless prank-turned-heart attack,  from the moped to the Seabass – it’s a perfect comedy. So incredibly funny.

3. Midnight Run

Midnight Run is a true classic. After he finished making The Untouchables with Brian De Palma, living legend Robert De Niro was looking to try something new and he chose comedy. De Niro’s efforts in the world of comedy have since fluctuated from the classically brilliant (Meet the Parents) to the painfully awful (Dirty Grandpa), but his first attempt was a home run. From Beverly Hills Cop director Martin Brest, Midnight Run tells the story of a bounty hunter (De Niro) who is sent to track down a criminal (Charles Grodin) who is wanted for stealing money from the mob to give to charity. Both the police and the gangsters he ripped off, as well as a rival bounty hunter looking to take the $100,000 score from De Niro, are chasing them across America. Their journey leads them into all kinds of peril: gunfights, helicopter battles, fist fights, and, of course, car chases. But, what’s really compelling in the movie is how De Niro and Grodin’s relationship develops, and how through sharing hardship and bickering, these adversaries become a pair of true friends.

2. Thelma and Louise

Ridley Scott’s Thelma and Louise has such a simplistic, minimalist premise – two women shoot a rapist and then hit the road in a ‘66 Thunderbird – and yet it transcends that to become so much more. For starters, it is the quintessential neo-feminist movie. In an article celebrating the movie’s 20th anniversary, Raina Lipsitz called it “the last great film about women.” The movie is a celebration of the power of women, but it’s remembered for its final scene. That scene encapsulates what we all wish we could do with our lives sometimes. We feel trapped or we reach a dead end, and we just wish we could embrace our companion and drive off a cliff. In a glowing review of the film, The New York Times said that Thelma and Louise “reveals the previously untapped talent of Mr. Scott (best known for majestically moody action films like Alien, Blade Runner, and Black Rain) for exuberant comedy, and for vibrant American imagery, notwithstanding his English roots. It reimagines the buddy film with such freshness and vigor that the genre seems positively new. It discovers unexpected resources in both its stars, Susan Sarandon and Geena Davis, who are perfectly teamed as the spirited and original title characters.” What a movie!

1. Planes, Trains, and Automobiles

The premise of the mismatched duo stuck on a cross-country road trip together is so tired and worn-out that you would’ve thought it had been exhausted of all energy and humor. But then you see Planes, Trains, and Automobiles, which sees Steve Martin’s workaholic ad executive stuck on a three-day journey with John Candy’s oafish shower curtain ring salesman to get home to Chicago to celebrate Thanksgiving with his family. The road trip antics – burning a car down with a cigarette, driving on the wrong side of the highway, two straight men cuddling in a motel room – are secondary to genuine care for the characters, and that’s ultimately why Planes, Trains, and Automobiles works so darn well. Leonard Maltin stated that this “bittersweet farce” is “amiable” and spends its running time masterfully “teetering between slapstick shenanigans and compassionate comedy.” A combination of the perfect pairing of Martin and Candy, the incomparable writing and directing work of John Hughes, and the heartstring-tugging final moments make this zany comedy gem a must-see classic.

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