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10 Best Road Trip Movies Handpicked by Way.com

  • Top Lists
  • Natasha Young
  • 7 minutes

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Unexpected twists and turns abound on road trips, whether they are roadside sights or backseat quarrels. Is it any surprise that this common way of travel has inspired so many filmmakers? Whether they’re funny, sad, whimsical, or violent — movies inspired by cars, buses, and motorcycles all have one thing in common: they all value self-discovery on the open road.

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While we all want to travel to new places and explore new cultures, we still fight against the pandemic. So obviously, one way to satisfy our wanderlust is to watch movie characters do it for us. It’s always fun to grab your favorite snacks and settle down to watch such amazing movies, especially during holidays. So, which are the best road trip movies actually worth watching? Gladly, we, the cinephiles at Way.com, are more than happy to help. So, buckle your seat belts and get ready for the amazing journey. 

1. It Happened One Night (1939)

Well, I proved once and for all that the limb is mightier than the thumb.” – Ellie Andrews

It Happened One Night is regarded as one of the first best road trip movies. Clark Gable and Claudette Colbert star as a sarcastic newspaper reporter and spoiled socialite, respectively. They end up on a cross-country trip full of flirtatious banter and screwball antics in the Frank Capra-directed film. The film was the first in history to win the “Big 5” Academy Awards (Best Picture, Best Director, Best Actor, Best Actress, and Best Screenplay). This clean sweep was an honor, but perhaps its most enduring legacy is the scene in which Colbert flashes her leg while hitchhiking. 

2. Bonnie and Clyde (1967) 

“This here’s Miss Bonnie Parker. I’m Clyde Barrow. We rob banks.” – Clyde Barrow

Bonnie and Clyde’s tagline pretty much sums up the film: “They’re young… they’re in love…and they kill people”” Arthur Penn’s 1967 classic, starring Faye Dunaway and Warren Beatty as the titular duo, is not only one of the coolest road trip movies ever made, but also an important breakthrough in American filmmaking. There had never been a mainstream Hollywood film with as much bloody violence (that final showdown!), and few other films have been able to replicate its sexy style. This classic was an inspiration to many filmmakers.

3. The Muppet Movie (1979)

“There’s not a word yet, for old friends who’ve just met. Part heaven, part space, or have I found my place”” – Great Gonzo

Music, mayhem, and muppets: the perfect ingredients for a road trip film. The Muppet Movie follows Kermit the Frog on his cross-country journey to Hollywood to pursue a career in show business. A journey punctuated by original songs, a slew of Muppet tagalongs, and an evil restauranteur with a burgeoning frog-leg business. If you enjoy puns, visual humor, and celebrity cameos, this is the movie for you. 

4. Planes, Trains, & Automobiles (1987)

“‘Cause I’m the real article. What you see is what you get.” – Del

Everything about Planes, Trains, & Automobiles works flawlessly. Not only does writer and director John Hughes expertly stymie Steve Martin and John Candy’s journey from New York to Chicago, but he also leaves us with a heartfelt and beautiful ending. However, it is the dynamic between Martin and Candy that has allowed it to stand the test of time and one of the best road trip movies. 

5. Thelma & Louise (1991) 

“Louise, no matter what happens, I’m glad I came with you.” – Thelma Dickinson

Best friends Thelma (Geena Davis) and Louise (Susan Sarandon) are looking to escape their drab lives in Arkansas in this film, and by the end of its 129 minutes, they have. With each passing year, Thelma & Louise gets better and better. Sure, the film’s ending is iconic. But the duo’s joyride down to Mexico is also full of laughs, heart, and action. In fact, while most would say Alien, Gladiator, or Blade Runner, there is a case to be made that this is Ridley Scott’s best film. 

6. Dumb and Dumber (1994) 

“We landed on the moon!” — Lloyd

Lloyd (Jim Carrey) and Harry (Jeff Daniels) abandon their dreams of opening a worm pet store in their hometown of Providence, Rhode Island, to return a lost briefcase to its owner in Colorado in this Farrelly Brothers comedy. The idiotic duo finally makes it to Aspen, but not before driving nearly a third of the way across the country in the wrong direction in Harry’s sheepdog-styled truck. Without a doubt, the dumbest film on this list. Also, most likely the wittiest entry. 

7. Almost Famous (2000) 

“It’s all happening.” – Penny Lane

Almost Famous, arguably Cameron Crowe’s last good film, is equal parts rock n’ roll and sugary sweet. The film follows a high school journalist (Patrick Fugit) who is given the opportunity to write a story for Rolling Stone about an up-and-coming rock band and leaves his overprotective mother to follow the musicians on the road. During his weeks on the band’s tour bus, the baby-faced teen learns valuable lessons such as the value of honesty, the futility of “coolness,” and the thrills and pains of first love. And if there was ever a movie to make the case for driving over flying, Almost Famous is it. 

8. Little Miss Sunshine (2006) 

“Olive, you are the most beautiful girl in the whole world.” – Grandpa

Suicidal brother, silent son, self-help obsessed husband, druggie father, and a seven-year-old daughter with dreams of becoming Little Miss Sunshine all join an overwhelmed mother on one of the most dysfunctional road trips in a beat-up VW bus. Having said that, the car problems, family fights, and detours aren’t all that unusual for an interstate adventure. This award-winning film has enough quirks and heart to last a lifetime, and the cast—which includes Steve Carell, Toni Collette, Abigail Breslin, and Alan Arkin—takes the craziness in stride. 

9. Into the Wild (2007) 

Happiness is only real when shared.” – Christopher McCandless

This Sean Penn-directed film, based on Jon Krakauer’s nonfiction book of the same name, follows the real-life travels of Christopher McCandless (Emile Hirsch) across North America and Alaska in the 1990s. Congratulations if you’ve made it this far in life without finding out how this story ends. Whatever happens, watching McCandless’ journeys, first in a Datsun Sunny and later in an abandoned bus, makes you want to hit the trail in one of America’s national parks—just maybe take a few wilderness survival classes first.  

10. Queen & Slim (2019) 

“Can I be your legacy?” – Queen 

Most blind dates end the moment they begin, but something about the one that begins Queen & Slim stands out right away. With New Orleans, Mississippi, and Florida as backdrops, this romantic crime drama depicts the social injustices that plague many African American communities. It’s a true love story with elements of slavery, feminism, masculinity, and religion. And it reveals the ebbs and flows of a relationship. As well as how life’s challenges can either push us apart or bring us closer together. Thelma & Louise did it for women and now Queen & Slim has done it for black Americans. They’ve taken the Bonnie & Clyde and Butch & Sundance on the run and remade them for a sometimes neglected audience, but with bang up to the present relevancy no matter where your sympathies lie.

These road movies may have ignited your wanderlust. When you are out on a road trip, don’t waste your time worrying about parking lots! With paved lots, well-lit spaces, and excellent service, you can find top-rated garages in your city through the Way parking app! Pre-book a spot by using Way.com’s extensive network of parking garages, and you can get amazing discounts in just a few swipes. Which one among these 10 is your favorite? If it’s already not on this list, let us know! 


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