Top 15 Travel Movies of the Last 50 Years

Top 15 Travel Movies of the Last 50 Years

BY Jeff Zanotti | February 14, 2022

If you’re yearning to travel like RIGHT NOW but shackled down to stationary life, we’re here to help you sit back and rediscover all the things we missed, hated or loved about traveling in the before times.

Movies take our protagonists on a metaphorical journey, but with travel movies they get taken on a physical journey that leaves them forever changed, for better or worse. Even with travel being forever altered, most of the movies on this list can provide a relatable escape, an introspective look at ourselves or well-needed laughs about something that used to be a part of our everyday lives.

Let’s set some criteria for this Top 15 Travel Movie list, though, before we start. My list, so my rules. No space travel or time travel and absolutely no multiverses (sorry, Marvel nerds). The journey itself must be a large part of the story, not just a device to set the movie into action for a fish-out-of-water type of film (e.g., “Coming to America,” “My Cousin Vinny,” “Lost in Translation”). I also did not want too much overlap, so I did not take more than one movie from a franchise and tried to limit repeating directors or writers when possible. As for the ranking criteria, these are not listed in order of how great I think the film is as a whole, but instead on its repeat watchability within the travel movie subgenre.

15) “Planes, Trains, and Automobiles” (1987)

The title alone pretty much buys itself a spot on any travel movie list, but John Hughes took a break from writing teen hits like “The Breakfast Club” and “Pretty in Pink” to write and direct this Thanksgiving trip home gone awry. Steve Martin and John Candy are the mismatched travel partners and do wonders playing off each other at the height of their comedic games. True to its name, it does feature all three forms of transportation, but I guess adding buses would have come off as too wordy. Similar to Hughes’ teen hits from the ’80s, this features a heart to it to go along with the laughs.

14) “We’re the Millers” (2013)

Jennifer Aniston finally found box-office success as a film’s leading lady when she teamed with a pre-”Ted Lasso” Jason Sudeikis as a pot dealer and Emma Roberts as a teenage runaway to pose as a fake family to smuggle in a large marijuana shipment from Mexico into the U.S. Though the critics were not big fans, Sudeikis displays early signs of his innate likability, and Aniston still had the goods post-“Friends.” Highlights include a super-awkward kissing scene and a very regrettable tattoo.

13) “Rain Man” (1988)

Horror movies always have to find a way to remove smartphones in order for its plot to not feel too contrived. For travel movies, that equivalent is eliminating air travel from the equation to set things in motion. “Rain Man” probably features the best way of doing this with Dustin Hoffman’s autistic savant character refusing to fly on any airline but Qantas, an Australian national air carrier, citing that they had never crashed. Thus our road trip with Tom Cruise and Dustin Hoffman as long-lost brothers begins. One of the most critically acclaimed movies on this list, it garnered four Oscars including Best Picture, Best Director, Best Actor (Hoffman) and Best Original Screenplay. The Las Vegas card-counting scene is a classic that was paid homage to in 2009’s “The Hangover.”

12) “Mad Max: Fury Road” (2015)

OK, this one definitely feels like an outlier, and possibly cheating to be added on the list, but I stand by its inclusion. It follows a group of protagonists toward a distinct and worldly destination, and this sets as the main plot of the story, so it follows the criteria I set up. It is not its fault that the nonstop action within this movie is so badass. Charlize Theron upstages the title character in this visually dazzling combination of car stunts and character designs taking place in the post-apocalypse Australian Outback yet filmed in the Namibian desert. Director George Miller deserves a ton of credit for making the fourth entry into his “Mad Max” franchise the most heralded.

11) “Pee-wee’s Big Adventure” (1985)

If you need proof of how weird the ’80s were, then look no further than the unlikely rise of comedian Paul Reubens’ stage persona Pee-wee Herman. His quirky man-child act gained popularity until a movie for it was finally greenlit. Who would you expect to direct a film about this nightmare fuel of a character? That’s right, Tim Burton, in his feature film directorial debut. Burton’s style and Reubens’ commitment to do a family-friendly version of Pee-wee led to this story of a lost bike being way more enjoyable than it should be. The success of this movie led to Pee-wee getting two additional movies and his own children’s TV series.

10) “Y Tu Mama Tambien” (2001)

Its premise of two teenage boys going on a road trip with an older woman sounds like the setup to a run-of-the-mill sex comedy, but it is far from that. This foreign-language film checks all the artsy boxes with hyper-realistic depictions of sex and themes of mortality and socioeconomic tensions between friends, all amidst the backdrop of a Mexico going through a time of historical political and economic change. Alfonso Cuarón flexes his directorial muscles years before he would win an Oscar for “Gravity.” This movie is a hard R or NC-17 depending on the version and not for the faint of heart, but definitely worth the watch.

9) “The Long Dumb Road” (2018)

Criminally underutilized by Hollywood, Jason Mantzoukas teeters between a comedic tour de force and a tragically broken human being in this coming-of-age movie about a sheltered college freshman-to-be as he embarks upon his trip from Texas to California. Despite the typical odd-couple setup, the film does a great job of going into predictable travel tropes before making sudden unexpected U-turns out of them. It never seems to linger in one mood or direction for too long.

8) “Almost Famous” (2000)

Coming of age is a common theme in travel movies as a metaphor for the journey into adulthood, but “Almost Famous” amps it up a notch as it has us follow a high schooler hired by “Rolling Stone” to follow the up-and-coming fictional band Stillwater on their bus tour across America. Cameron Crowe as writer/director hits all the notes just right, allowing the audience to relive the thrill of first-time autonomy and first crushes. The soundtrack exposed a new generation to Elton John’s “Tiny Dancer” during one of the film’s most heartfelt scenes. Cameron Crowe netted an Oscar for Best Original Screenplay and Kate Hudson was propelled into stardom as “band aid” (don’t call her a groupie) Penny Lane.

7) “Thelma & Louise” (1991)

With two affable leads in Susan Sarandon and Geena Davis, this traveling crime duo at a glance reminds you of a female “Butch Cassidy and the Sundance Kid,” but it is inundated with important themes revolving around females’ experiences with and reporting of sexual assault, giving it gravitas. Despite the constant reminder of real consequences to their actions, the friendship between the title characters shines through. The strength of this friendship reaches its apex in the iconic final shot.

6) “Paper Moon” (1973)

My parenting goal has always been to be a little better of a dad than Ryan O’Neal. Luckily, he set the bar so low you need a shovel to reach it. His real-life daughter Tatum, who was only 8 years old at the time, joins him as a grifting team that makes their way across Great Depression-era Kansas and Missouri. The late Peter Bogdanovich beautifully captures the desolate landscapes, and a cigarette-smoking Tatum won an Oscar for her role. You will learn plenty about how grifting was done before the internet made it as easy as posing as a Nigerian prince.

5) “Up in the Air” (2009)

In stark contrast to other entries on this list, the Jason Reitman-directed film highlights not only air travel but also comments on the loneliness of travel. George Clooney wonderfully plays the lead who is hired to fly from city to city to fire employees that their own businesses are too cowardly to in person. This movie hit really close to home for the time as it came out at the end of the Great Recession. Despite it embracing and even glorifying at times the isolation that comes with the lead’s travels, it is filled with bittersweet and funny moments. The supporting cast gets a jolt from then-barely known Anna Kendrick and Danny McBride.

4) “Tommy Boy” (1995)

In his short time on this earth, Chris Farley created many memorable characters in film and TV, but his Tommy Callahan is easily one of his best. Tommy is well meaning but bumbling and not academically inclined. In order to save his family’s company after the unexpected death of his father and the company’s owner, he hits the road with fellow “SNL” alum David Spade to meet in person with their customers. This leads to incredibly disastrous results. There is not much to the plot but it doesn’t matter, as this film is at its strongest when focusing on the interactions along the road between Farley and Spade.

3) “Smokey and the Bandit” (1977)

Burt Reynolds is at his most charismatic as a bootlegger and Sally Field is at her most endearing as a runaway bride in this hour-and-a-half Coors commercial masquerading as a Hollywood hit. The premise alone will bend your mind. Reynolds has to transport 400 cases of Coors from Texas to Georgia because, get this, Coors was illegal east of the Mississippi prior to 1986, when it became nationally distributed. This now-macro-brew was once a regional beer that was considered a delicacy to those in the eastern part of the country. Bandit was making Coors cool decades before Johnny Lawrence did in “Cobra Kai.”

2) “National Lampoon’s Vacation” (1983)

For those raised in the ’80s, this movie is the first movie that comes to mind when you think of family vacation. Produced at a time when the name National Lampoon actually carried some weight, “Vacation” held its own and started its own franchise. Chevy Chase was at arguably his most famous as the patriarch that makes the terrible decision to drive from their home in Chicago to the fictional amusement park Walley World in southern California despite his family’s insistence on flying. What follows includes unfortunate consequences for not just the family but also more dire early trip ends for Aunt Edna and her dog Dinky. Christie Brinkley makes an iconic cameo, but it is Randy Quaid who steals the movie as cousin Eddie. This movie made wood-panel station wagons as synonymous to family vacations as Miatas were to midlife crises.

1) “Kingpin” (1996)

The Farrelly brothers are most commonly remembered for “Dumb and Dumber,” but it’s their movie about bowling hustlers that takes the top spot for this list. With winks to great hustling movies like “The Color of Money,” it walks the line from homage to stand-alone comedic masterpiece. Woody Harrelson is perfect as the broken-down, one-handed bowler trying to get back into the game. Bill Murray could be one of the greatest comedy villains in movie history with his role of Big Ernie McCracken, whose ego is only matched by his hair. A great soundtrack makes the movie flow perfectly from scene to scene and throughout the hysterical montages. You will be hard-pressed to find a movie with better throwaway lines than “Kingpin.” Early in the movie a character is asked, “How’s Life?” and I still laugh hysterically at the deadpan immediate response of, “Taking forever.” It didn’t win any Oscars, but I am never turning it off when it comes on.