Road Trip movies are an interesting sub-genre that can span all sorts of genres. The films can be completely slapstick and stupid to the extremely poignant and Academy Award-winning dramas. Regardless, it is all about a real journey that typically lends itself to a metaphorical one in the lives of the main characters. It is about growth and it is about discovery. Here is the list of the best road trip movies of all time.
#30 Over The Top
The eighties were an interesting place. You could put Sylvester Stallone in almost anything and it would succeed. That theory was tested when in 1987 when Warner Brothers decided to launch a film about Sly entering the world of competitive arm wrestling to win back custody of his son. The film is beyond cheesy, but worth a watch. They somehow take the subject seriously and find a way to insert some excitement into what must be the worst spectator sport of all time.
#29 Wild Hogs
In the 2000s we started to see the “old-timer” genre really gaining popularity and distributors were seeing that the older filmgoing community was underserved and thirsty for stories they could relate to. One product of this thinking was Wild Hogs, a film about four older biker gang wannabes who set out looking for a little excitement and maybe find a bit too much. This film is also very cheesy, but heartwarming at times and a delight to see the mix of high caliber old-timers (Travolta, Martin, Allen and Macy) coming together for a comedy film.
SEE ALSO: 20 Best Old-Timer Movies of All Time
#28 The Wizard
This kids movie is one of those films that could have easily disappeared but has stuck around because of how fondly adults remember this 1989 film about a group of kids making their way to the Mecca of video game competitions. Even though the film basically plays like a 1 hour 40 minute Nintendo commercial (with sexy power glove stop down to boot), the hope and dynamics of the group of kids mixed with that trademark Fred Savage “I not know about this” humor makes for a film that has stood the test of time. It is super dated but it holds up. This is one of two kids films to make the best road trip movies list and that says a lot.
#27 Midnight Run
Robert DeNiro plays a bounty hunter in this 1988 buddy cop action-comedy. Do I even need to go any further? Probably not but just for good measure, the film is directed by the great Martin Brest (Beverly Hills Cop, Scent of a Woman) and is about an accountant that embezzles $15 million dollars from the mob and has the aforementioned bounty hunter race across the US to find him. The film has heart, is a lot of fun, and it is one of the more unique performances from the great DeNiro. An easy winner of the honor to be one of the Best Road Trip Movies.
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#26 We’re The Millers
This film, about a fake family on the run from trouble, could have easily been one of those comedies that does its job of being funny and then just drifts off into the background. It wasn’t though because it was so so funny and had the incredible charisma and chemistry of leads Jason Sudeikis and Jennifer Aniston, as well as, their “kids” played by Emma Roberts and Will Poulter.
#25 Away We Go
Funny in a dry way, this one is more of a dramatic addition to our list. A couple who is expecting their first child travel around the U.S. in order to find a perfect place to start their family. Through different trips around the US, and through an eclectic group of friends and family, this couple explores what is truly important about building a “home”. In addition to the great writing Dave Eggers and Vendela Vida, and direction by Sam Mendes, we also get two truly special performances from John Krasinski and Maya Rudolph in a way we have never seen them before.
#24 Road Trip
Before the super smash hit The Hangover, writer/director Todd Phillips brought us this 2000 entry to best road trip films about a college student making a foolish trip across the country to save his relationship only to realize through the trip it is not something that he needs at all. The writing is hilarious and we get some incredibly iconic roles in Breckin Meyer, Seann William Scott, Tom Green and ultra nerd DJ Qualls. If you were ever curious about things like whats make cheating, cheating, then this outrageous laugh out loud comedy is for you.
#23 Easy Rider
This 1969 drama was written by Peter Fonda and Dennis Hopper, so you know its got a drug-fueled poetic yet cool vibe. After smuggling cocaine from Mexico to Los Angeles, two freewheeling motorcyclists ride eastward. Drugs, arrests, confrontation, social issues, Jack Nicholson… this film was a cultural milestone of the time and has it all.
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#22 Harold and Kumar Go To White Castle
It is hard to get a much more “stoner adventure” than a film about two dudes just trying to get White Castle. This little film is ridiculous and leans into it hard. John Cho and Kal Penn play two pressed minorities that are just trying to live their lives. When they set out on a journey for sliders, they run into some incredibly interesting characters including a drugged up parody of Neil Patrick Harris played by Neil Patrick Harris, a deformed Christian man with a beautiful wife he wants the two leads to sleep with or a group of idiot white dudes who infuse their lives with Mountain Dew in order to be the right level of “EXTREME!” What could have been an easily forgotten trip, has stood the test of time and spawned many sequels.
#21 Pee-Wee’s Big Adventure
The very odd Pee-Wee, a character portrayed by Paul Reubens, was blowing up on his weird small screen show. This made equally as weird soon to be super director Tim Burton (Beetlejuice, Edward Scissorhands) think he should make the jump to the big screen in his directorial debut. The result is movie magic history. Pee-Wee sets off across the US to find his stolen superbike and meets plenty of interesting characters along the way.
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#20 Thelma & Louise
A story about friendship and running from the law. This 1991 film follows the great Susan Sarandon and Geena Davis on a journey to run from their pasts. A dramatic adventure, this cultural milestone was brought to life by Ridley Scott (Blade Runner, Gladiator, The Martian) and the end result shows it. You have to travel far and wide to meet someone who hasn’t heard of this iconic pair. A definite must-watch on the list of Best Road Trip Movies.
#19 Borat: Cultural Learnings of America for Make Benefit Glorious Nation of Kazakhstan
Borat is rockumentary meets outrageous uncomfortable comedy. Master of disguise Sacha Baron Cohen plays a fake character, a man from Kazakhstan that comes to America to learn more about their culture. The film is real, the people involved think it is real, but it very much is not. Borat plays the “I don’t understand your American culture” routine over and over and gets himself into some interesting situations as he makes his way across the US.
This film was just a little independent movie that blew up hard strictly based on how funny it was. The film stared almost no one you would recognize at the time (expect a wonderful cameo from Matt Damon) but it didn’t matter. A group of friends graduating high school decide they need to go on one amazing trip before they lose touch and their lives are set forever. Due to a penal situation, that place ends up being Europe and oh man do they get in over their head. You will laugh out loud over and over. And remember, Scotty doesn’t know.
#17 Almost Famous
Writer/Director Cameron Crowe (Jerry Maguire) understands characters and he understands music. Those two things intersect in spades in this film, which could easily be called his best. Based on a true story, a young wide eyed kid gets a chance to write a piece for Rolling Stone magazine in it’s heyday and go on tour with fake Allman Brothers esc band Stillwater. It is uplifting and life affirming at times and it is sad an lonely at others. You will go on a journey as long as the lead as you watch this amazing road trip film.
#16 Captain Fantastic
Viggo Mortenson received an Oscar nomination for his role of head of a traveling family in this quirky comedy. It is very much in the vein of Little Miss Sunshine but has a deeper dramatic family connection similar to the Woody Harrelson / Brie Larson vehicle The Glass Castle. You will laugh, you will cry, but you will enjoy this journey of a family experiencing the real world for the first time.
#15 The Muppet Movie
The muppets are one of those beloved properties that has been around since 1976 and is just as relevant and as known today. It started as a primetime tv show but in 1979 the Henson company decided to take it to a big screen road trip movie adventure. The movie centers around Kermit the Frog meeting his ragtag crew and heading off across the country to find success in Hollywood. Even though the film is rated G, don’t let that fool you, the dialogue and situations are smart, helping propel this one to a cult classic.
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#14 Into the Wild
What happens when a man sells all his worldly possessions and travels to Alaska to be more one with nature? This provocative independent spirt darling from writer/director Sean Penn shows it and shows it well. Emile Hirsch gives and incredible and dramatic performance that relies mostly on you experiencing his inner turmoil. It is a little tough to watch at times but you will come out the other side a better person.
#13 The Trip
The trip started out as a British TV series to be a vehicle for the beloved personalities of Steve Coogan and Rob Brydon, but became so popular, many theatrical films were made. The pair play versions of themselves where they are asked by a famous publication to tour the best restaurants of the country. Originally supposed to go with his girlfriend, she backs out and he is forced to take his best friend, who he very much has a love-hate relationship with.
You aren’t confused, this is a dramatic 2013 film is in fact in black & white. Director Alexander Payne (Sideways, The Descendants) wanted to set a very drab tone for this film about a grizzled old man and his estranged son who must drive to Montana to claim a lottery prize. The film is very much that, grizzled and drab. It is very somber by layered with so much and a true window into family and life.
Just beating out another one of his films, Alexander Payne brings us this other memorable road trip film about life happening in Sideways. The film stars Paul Giamatti and Thomas Haden Church who are in different stages of mid-life crisis and decide to take a week-long tour across California’s wine country. It is very much a drama but has its light humor. The film won an Oscar for best script and that was no mistake, it is that good.
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#10 Fear & Loathing in Las Vegas
I don’t think any film in the history of cinema has come close to the psychedelic drug-fueled journey that is Fear & Loathing in Las Vegas. Based on a story in the life of prolific writer Hunter S. Thompson and directed by equally interesting Terry Gilliam (Monty Python and the Holy Grail, Twelve Monkeys), the film has stood the test of time. Johnny Depp and Benicio Del Toro give tremendous performances as Hunter and his doctor/drug dealer respectively.
#09 Dumb and Dumber
The careers of Jim Carey and Jeff Daniels were truly launched into the hemisphere after playing a couple of idiot best friends who travel across the country to find a woman they are convinced they are in love with to return a briefcase they should have never picked up. The writer/director team The Farrelly Brothers (Something About Mary, Me Myself and Irene) brought this one to life if that tells you anything. This best road trip film entry is laugh out loud funny at all the stupid moments this good-hearted pair gets into, but it is also warm and very satisfying. It spawned two sequels but none were able to capture the magic of this first film.
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#08 Y Tu Mamá También
The great Alfonso Cuaron has won two separate best director Oscars (Roma, Gravity) but before that, he stunned the world with the great loosely autobiographical film Y Tu Mama Tambien. It is about a cross country trip filled with very interesting and relatable self-discovery.
#07 Planes, Trains & Automobiles
John Candy is another comedian on our list of best road trip films that left this Earth way too early. Though he died in 1994 at the age of 44, he brought many great cult movies to the screen and this is definitely one of them. Steve Martin is an uptight businessman trying to get home for Christmas and everything that can goes wrong does. He meets up with John Candy and together they team up to do what ever it takes to make it back home.
#06 Rain Man
This 1988 film delivers on absolutely everything. It was directed by Barry Levinson and stars the top of their games Tom Cruise and Dustin Hoffman. Cruise plays a prick who must come back to his estranged family to transport his savant brother across the country in order to collect a giant inheritance for his father. Cruise over time realizes he has been terrible and grows to accept his autistic brother once again. The film won four Oscars including best picture and if you watch even a few minutes, you will know why.
#05 Little Miss Sunshine
This prime example of the best road trip movies is one of the feel-good movies of the century. This story about a little girl trying to find glory and her eccentric family helping her get there will warm your heart and make you laugh. The film put together a tremendous ensemble in Alan Arkin, Paul Dano, Steve Carell, Toni Collette, Greg Kinnear and an unknown Abigail Breslin. The film was nominated for three Oscars and took home two (best original script, best-supporting actor Alan Arkin).
#04 Tommy Boy
Quite easily one of the best comedic duos of the modern-day is that of David Spade and Chris Farley. They only got to make two films together before Farley’s life was prematurely surrendered to drugs, but they were good ones. The arguably best one being Tommy Boy, about a good-hearted rich idiot who must save his father’s company by closing a major auto-parts deal with Dan Aykroyd. He must drive across the country to do it and only has the weasely tight-ass company executive played by David Spade to help. This is an odd-couple buddy flick with comedic situations that live up to the talent of these two comedic greats. You will laugh, you will cry, you will watch it over and over. Shout out to the other film, BLACK SHEEP, which could easily make this list of best road trip movies, but is the same film.
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#03 National Lampoon’s Vacation
In 1983 the world met The Griswald’s in this hilarious #3 hit on the best road trip movies list. Chevey Chase was the master of a dry satirical meets physical comedy type of style that happens over an over in this gem. Clark, his wife, and two kids taking a family trip across the country to Wally world for a family vacation and about everything goes wrong. There are so many things from this film that are parodied or referenced, and it would go on to spawn many sequels.
#02 Blues Brothers
Blues Brothers is not only one of the best road trip movies of all time, but one of the best comedies of all time, with one of the best duo of characters of all time. Dan Aykroyd and John Belushi play the Blues Brothers who travel across the country to reunite their Blues band for one big reunion show. The characters skirt the law and do what they need to do, but the fun part is that they do it all in the coolest way possible.
#01 Green Book
Quite easily #1 on the list of best road trip movies in the Oscar winning Green Book. The film stars the great Viggo Mortenson as a blue collar, hardly can read, Italian American smooth talker. Mahershala Ali (who won an Oscar for this role) is a well educated affluent musician who wants to tour the Deep South to help stop the racism of the 60s. He recruits Tony lip (Viggo) to be his driver and over the coarse of the film, learn a great deal about one another and ultimately become friends. The film is funny in all the right moments, warm in all the right moments, impactful and dramatic. You will feel like you just had a two-hour-long hug after watching this film.