The Best Road Trip Movies of All Time

The Best Road Trip Movies of All Time

Few things are better than a classic road trip. Sun shining, music blaring, wind in your hair, and some good friends. But since road trips aren’t exactly a thing you can schedule every day, sometimes you have to make do with watching other people go on their own epic journeys. For that, we have 20 of the best road trip movies of all time.

Road Trip (2000)

With a title that says all we need to know, Road Trip is a who’s who of stars from the teen sex comedy genre that dominated the early 2000s. The film is raunchy and hilarious, capturing that youthful energy of adventuring with your friends and having everything spiral out of control. Released in 2000, the movie feels like a send-off to the ‘90s, full of countless references and cast members that were part of iconic ‘90s productions ranging from American Pie to Rent.

Nomadland (2020)

Any movie that wins three Oscars, including Best Picture and Best Director, is sure to make its way to the top of any best-of list, and that’s exactly the case here. Frances McDormand shows that even two decades after also starring in Almost Famous, she can still make one hell of a road trip movie in this story about packing up your essentials and roaming the country in search of purpose.

The Blues Brothers (1980)

Considered by many to be the greatest Saturday Night Live spinoff film of all time, The Blues Brothers stars John Belushi and Dan Aykroyd road-tripping around the state looking to get their old band back together. The movie was a box-office and cult hit, eventually spawning a sequel that unfortunately failed to live up to the high bar set by the brothers.

Y Tu Mamá También (2001)

Travelling to a secluded beach on the Mexican coast may not sound like the most exciting destination, but it’s times like that where it’s important to remember the journey is always more important. A story of two teenage boys travelling with a woman in her late twenties, the film depicts jealousy and self-discovery against the backdrop of Mexico’s political turmoil. The movie was so popular, it set the record for the highest box-office opening in Mexican cinema history.

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Thelma & Louise (1991)

Seen as one of the greatest feminist films of all time, Thelma & Louise is also just one of the greatest films of all time, road trip or otherwise. It portrays two best friends adventuring on the road together and quickly spiralling into crime and running from the police. The controversial film became instantly beloved by audiences everywhere, earning six Oscar nominations and winning Best Original Screenplay. In 2016, it was added to the Library of Congress’s National Film Registry for its cultural significance.

Easy Rider (1969)

If you’ve ever seen a movie or show where Steppenwolf’s “Born to Be Wild” blasts as people drive off, you have Easy Rider to thank for that seminal moment. The movie was iconic for its portrayal of rising counterculture movements such as hippie culture, anti-war protests, and recreational drug use. It’s a fun movie about venturing off to New Orleans and leaving social tension behind.

Dumb and Dumber (1994)

Widely considered to be one of the greatest comedies of all time, Dumb and Dumber showcases a journey from Rhode Island to Colorado that is full of as many shenanigans as one could possibly pack into 107 minutes. The movie’s popularity has led to two sequels and even an animated television show, as people couldn’t get enough of watching these two goofballs have fun on the road together.

Death Proof (2007)

A road trip movie-turned-brutal slasher flick is about as Quentin Tarantino as anything can get, which is what makes it the perfect twist on the genre. Released in North America as Grindhouse, a double feature alongside Robert Rodriguez’s Planet Terror, the movie was a box-office failure that taught Tarantino a few lessons. Nevertheless, the movie has since become a cult hit, for viewers who discovered it without having to sit through a second movie.

Inside Llewyn Davis (2013)

Travelling from New York City to Chicago and back may not sound like the most thrilling road trip, but the Coen Brothers are capable of turning nothing into something enthralling. In classic Coen fashion, this is a movie that twists the road trip trend, instead offering a look at a down-on-his-luck folk singer trying to make ends meet rather than the hijinks and hilarity the genre usually offers.

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Into the Wild (2007)

Who hasn’t found themselves disenchanted with society and debated giving away all their possessions to hitchhike across the country and live in the wilderness? Fortunately, that’s exactly the journey that Into the Wild portrays, telling the biographical story of Christopher McCandless, who met all sorts of people on his journey out to live in the Alaskan wild.

It Happened One Night (1934)

One of the first road trip movies of all time, this 1934 classic starring Clark Gable and Claudette Colbert is famous for its iconic ankle flaunting scene that has been parodied an endless amount of times. It’s widely considered to be one of the greatest films ever, as the rom-com is filled with endless comedic moments as the pair venture out to New York. It was also one of the last movies released before the Motion Picture Association began stricter enforcement of the Motion Picture Production Code, which severely limited what films could show for nearly three decades.

Midnight Run (1988)

Robert De Niro in a New York to Los Angeles buddy comedy, need anyone say more? The film was both a critical and commercial success, spawning three made-for-TV sequels expanding on the story of various characters throughout the film. With De Niro playing a bounty hunter, the movie perfectly blends hysterical comedy with thrilling excitement and a few heavier, dark moments to keep audiences guessing.

Planes, Trains and Automobiles (1987)

When Steve Martin, John Candy, and John Hughes collaborate on a movie together, the result is sure to be… well, as good as Planes, Trains and Automobiles is. The movie is about a three-day journey to Chicago between two unlikely travel companions—like if The Odd Couple happened in transit. It’s a must-watch performance for both Martin and Candy, with Roger Ebert calling the film “perfectly cast and soundly constructed.”

Little Miss Sunshine (2006)

A tiny budget and an all-star cast led this movie, about travelling to a California child beauty pageant, to become one of the greatest surprise hits of all time. Little Miss Sunshine, won two Oscars, including Best Original Screenplay, and made over US$100 million on just an US$8-million budget. It’s the perfect example of how a beat-up van and a cast of weirdos can be just as engaging as a team of superheroes.

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The Cannonball Run (1981)

What’s more exciting than a road trip from Connecticut to California? What about if that road trip was all part of an illegal race across the country? That’s exactly the plot of The Cannonball Run, in which an all-star cast that includes Burt Reynolds, Roger Moore, Dom DeLuise, Farrah Fawcett, Dean Martin, Sammy Davis Jr., and Jackie Chan all race from coast to coast. The Cannonball Run continues to live on in road trip lore with the record having been broken countless times over the years.

National Lampoon’s Vacation (1983)

The National Lampoon’s series has produced some wonderful movies, but Vacation is widely considered to be the best of them all. With John Hughes, Harold Ramis, and Chevy Chase all collaborating on this movie, it’s no surprise that it’s an endless stream of laughs with just the right amount of heartfelt moments sprinkled in.

Rain Man (1988)

Dustin Hoffman and Tom Cruise each give perhaps the best performance of their careers in this iconic movie. The film was a success in every sense of the word, becoming the highest-grossing film of 1988, making over US$350 million on just a US$25-million budget, alongside winning four Oscars including Best Picture, Best Director, Best Original Screenplay, and Hoffman winning Best Actor. It’s a cross-country road trip about self-discovery and never underestimating people—an absolute must-watch.

Smokey and the Bandit (1977)

Burt Reynolds’ directorial debut was everything anyone could have hoped for, with his hilarious and exciting film about a bootlegger and runaway bride trying to smuggle 400 cases of beer from Texas to Atlanta. It was a massive hit, with only Star Wars outperforming this iconic 1977 film at the box office. The on-screen chemistry would even blossom into a real relationship between Reynolds and co-star Sally Field.

True Romance (1993)

As if travelling from Detroit to Los Angeles wasn’t exciting enough, doing so while being chased by the mob is sure to add some excitement to the road trip. This film marks one of the rare instances of Quentin Tarantino writing the screenplay, but not directing as well, which many people credit for its success.

Almost Famous (2000)

In this semi-autobiographical story, a young Rolling Stone journalist follows around a touring rock band, getting in all sorts of hijinks along the way. Love, sex, partying, and meeting all sorts of new people make this movie a coming-of-age tale as much as a road trip movie. It’s an absolute must-watch for music lovers, and those who dream of hitting the road and partying every night.

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