10 Hilarious Road Trip Movies to Watch Before Your Next Vacation

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Road trips are one of the most exciting ways to explore the world, discover new places, and make unforgettable memories. But let’s be honest: long hours on the road can also be tiresome and even dull at times. That’s where movies come in handy! 

Pack Your Bags, but First, Pop the Popcorn!

National Lampoon's Vacation movie
Image Credit: Warner Bros.

In this list, we’ll look at ten comedies that will not only entertain you but will get you in the mood to hit the road. From classic road trip flicks to comedies that mix the laughs with the tears, these films will tickle your funny bone and inspire you to see where the road takes you.

1. Midnight Run (1988)

scene from Midnight Run
Image Credit: City Light Films.

Have you ever wanted to see a road trip comedy starring Robert DeNiro as a tough-as-nails bounty hunter? That’s a rather specific dream; luckily, 1988’s Midnight Run is precisely that. 

DeNiro plays Jack Walsh, a tough-talking bounty hunter tasked with bringing Charles Grodin’s character, an embezzling accountant named Jonathan “The Duke” Mardukas, back to Los Angeles to face trial. However, as a general rule in every road trip flick, things rarely go smoothly for these two.

2. Zombieland (2009)

Zombieland road trip movie
Image Credit: City LightsTriStar.

Funnily scary (or scarily funny,) Zombieland isn’t afraid to mix the laughs with the gasps. This 2009 horror-comedy stars Jesse Eisenberg, Emma Stone, Woody Harrelson, and Abigail Breslin as lone survivors in an America ravaged by a zombie apocalypse. The four embark on a “family” trip, in search of a new place to call their home.

Thanks to its witty dialogue, gratuitous zombie gore, and even an unforgettable cameo by Bill Murray himself, Zombieland is the perfect companion for an apocalyptic road trip. Just be sure to pack enough Twinkies for the ride!

3. The Blues Brothers (1980)

The Blues Brothers - road trip movie
Image Courtesy: mptvimages.com.

It’s rare to come across a road trip film that’s also one of the best musical comedies ever made. That might be why The Blues Brothers is the only flick I can think of that fits that description. This wild comedy sees legends Dan Aykroyd and John Belushi as Elwood and Jake Blues, two brothers on a divine mission to save their childhood orphanage from debt.

This musical journey takes us through almost all of Illinois, with a particular focus on the Windy City itself. Of course, the film’s highlight is the crazy car chase near the end, when the Brothers escape through the streets of Chicago. Dozens of police cars and a squad of National Socialists aren’t enough to stop the Blues Brothers, though.

4. Sideways (2004)

scene from Sideways - a funny road trip movie
Image Courtesy: Fox Searchlight Pictures.

Wine lovers rejoice! Sideways is a movie that captures the elegance and beauty of the Santa Ynez Valley, complete with its wineries and unforgettable vistas. It’s also a hilarious film to watch if I might add. 

Sideways stars Paul Giamatti as a writer and wine enthusiast who travels to California’s wine country with his womanizing friend, Jack. Of course, things get a bit rocky for the pair once they meet two women that challenge their beliefs in love, women, and wine. 

If you prefer your comedies to have witty banter instead of gross-out shenanigans, then Sideways is the movie for you.

5. Dumb and Dumber (1994)

scene from Dumb and Dumber
Image Courtesy: New Line Cinema.

A trip across the country with the dumbest comedy duo ever conceived? What could possibly go wrong? Dumb and Dumber follows the misadventures of Harry and Lloyd, two dimwits on a mission to return a lost briefcase to its rightful owner. However, these two geniuses ignore the fact that the briefcase contains ransom money for a kidnapping plot.

Starring Jim Carrey, Jeff Daniels, and a dog van, Dumb and Dumber remains a classic of gross-out humor from the Farrelly brothers, the ones responsible for classics such as Shallow Hal and There’s Something About Mary. The film spawned a couple of sequels – and even an animated TV show – but none are as funny as the original. You just can’t go wrong with the classics – or with 90’s Jim Carrey in general.

6. Planes, Trains, and Automobiles (1987)

scene from Planes, Trains, and Automobiles
Image Credit: Paramount Pictures.

Road trips take many shapes and forms. Sometimes, there isn’t even a “road” in the road trips. That’s something that Planes, Trains and Automobiles illustrates, complete with how hectic improvised travel can be.

The film pairs Steve Martin and John Candy – two unlikely travel companions that do everything possible to be home for Thanksgiving, including riding the aforementioned planes, trains, and automobiles. Over everything else, this is a rather heartwarming film that teaches us the importance of finding common ground with those that irritate us. 

Also, it’s a great PSA for keeping your eyes peeled on the road, no matter how catchy Mess Around by Ray Charles might be.

7. Due Date (2010)

scene from Due Date
Warner Bros. Entertainment Inc.

2010’s Due Date combines the stress of a road trip with a stranger with the anxiety of childbirth into one memorable wild ride. The odd couple at the center of the show is Peter (Robert Downey Jr.,) a soon-to-be father whose life gets thrown upside down by an eccentric aspiring actor, Ethan, played by Zach Galifianakis. 

The film takes us on a crazy journey from Atlanta to Los Angeles – with a bizarre detour to Mexico for good measure. Can these two oddballs find some common ground as they discover more about themselves in this life-changing journey? Probably not. Still, it’s pretty funny to watch them try.

8. The Hangover (2009)

scene from The Hangover
Image Credit: Warner Bros. Ent.

Before Due Date, Todd Phillips reached the pop culture zenith with The Hangover, a comedy of errors that follows a group of friends at a wild bachelor’s party in Las Vegas. However, when the groom mysteriously vanishes after a night of partying, the “Wolf Pack” will have to piece together the events that transcurred the previous night, all while dealing with colossal hangovers.

More than anything, The Hangover combines unforgettable moments that have become landmarks in modern comedy. I mean, who could forget the tiger in the bathroom? While this might not be the most “varied” road trip out there, it’s still a great advertisement of what not to do when visiting Las Vegas. Or any city in general.

9. Little Miss Sunshine (2006)

scene from Little Miss Sunshine
Image Credit: Twentieth Century Fox.

The epitome of the modern road movie, Little Miss Sunshine is an indie darling that never fails to make us laugh – and cry. The story follows a dysfunctional family embarking on a cross-country road trip to take their daughter to a beauty pageant. Along the way, we get to see the secret struggles of the Hoover family as they finally learn to come together as a family – on their own terms.

Perhaps one of the best parts about Little Miss Sunshine is its talented all-star cast, featuring heavyweights such as Toni Collette and Steve Carell. Coincidentally, Abigail Breslin stars as the lovable Olive Hoover. A few years later, she would also star in Zombieland, making her a certified road trip comedy expert in our books.

10. National Lampoon’s Vacation (1983)

scene from National Lampoon's Vacation
Image Credit: Warner Bros.

If there were ever a movie that captures the spirit – and the chaos – of the classic all-American road trip, that would be National Lampoon’s Vacation. The first entry in this legendary comedy series came out in 1983, and it introduced the world to the chaotic misadventures of the Griswold family.

The first movie follows the Griswolds in a misguided attempt by Clark, the family’s patriarch, to bring his family closer together. What ensues is one of the most hectic comedies ever made, introducing a bizarre cast of characters and some morally questionable situations with every passing mile.

If you’re planning to embark on a road trip of your own soon, Vacation might be the perfect guidebook for what to avoid on such occasions. Also, you might want to call Walley World before you visit – they may be closed for repairs.

10 Highest Grossing Movies of All Time (Inflation Adjusted)

Star Wars The Force Awakens Harrison Ford
Image Credit: Lucasfilm

Ever debated the greatest movies? Well, we’re counting cash, not critics. Here’s an inflation-adjusted roundup of the top 10 box office champions—because modern-day blockbusters can’t just inflate their way to the top! This list represents the highest-grossing movies of all time.

10 Highest Grossing Movies of All Time (Inflation Adjusted)

Best 10 Movies to Watch Before Visiting New York

Taxi Driver movie
Image Credit: TriStar Pictures.

Heading to New York and want some cinematic inspiration for your itinerary? These 10 classic movies are just what you need to set the mood for your trip!

Best 10 Movies to Watch Before Visiting New York

10 Awesome Movies to Watch if You’re a Fan of Top Gun

Top Gun - Maverick
Image Credit: Paramount Pictures.

Strap in because we’re going to explore the 10 best movies to watch for all you Top Gun fans!

10 Awesome Movies to Watch if You’re a Fan of Top Gun

12 Most Recent Movies to Join the Billion Dollar Club

Ryan Gosling in Barbie movie
Image Credit: Warner Bros.

Raking in $1 billion at the box office is no laughing matter for a movie. In fact, only 53 total movies have ever accomplished this amazing feat. In this list, we’re going over the most recent 12 films to join the billion-dollar club. If you’ve been looking for a new(ish) movie to watch that is undoubtedly approved by the masses, try one of these out and see for yourself why it was so popular amongst movie-goers.

Here’s What It Was Really Like to Drive a Model T Ford

Model T wreck
Image Credit: Deposit Photos.

Tired of driving down easy-street in your super comfy modern car? Well, have no fear because the Model T is here! Let’s take a ride down memory lane with a humorous look at what traveling in a Model T was like when it first came out.

Here’s What It Was Really Like to Drive a Model T Ford

This article was produced and syndicated by Our Woven Journey. Featured Image: Paramount Pictures.

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Demi Michele is a seasoned traveler, turned freelance writer. Having explored most states and ventured internationally, her love for outdoor cafes, new cuisines, and cultural immersion shines through her wide range of articles. Based in Texas with her family and two Scottish Terriers, Demi turns her adventures into captivating travel narratives to share with readers.