Last Updated on August 3, 2021
#1 – NATIONAL LAMPOON’S VACATION
Was there any other choice for #1? Harold Ramis, John Hughes, and Chevy Chase made something truly special with VACATION, something that they failed to capture in any of the sequels or spin-offs. While some of the follow-ups have their own moments and merits, the original VACATION exemplified the National Lampoon brand of movies while giving us iconic moments and scenes that have made their way into almost every other movie on this list than came after it. From the song “Holiday Road” to Christie Brinkley, every scene in VACATION is a classic.
#2 – PLANES, TRAINS AND AUTOMOBILES
John Hughes was already the master of the teen movie but in 1987 he mastered the road trip movie. Few actors as hilarious as Steve Martin have done a better job at playing the straight man, but it is his restrained turn of a slowly unravelling man alongside the manic and annoying John Candy. Together, they made an immortal screen duo in the same vein as Bing Crosby and Bob Hope. The heartfelt ending just helps cement how much these two very different men come together after a nightmarish trip.
#3 – THELMA & LOUISE
What BUTCH CASSIDY AND THE SUNDANCE KID did for horses, THELMA & LOUISE does for convertibles. Two outlaw women on the run from the law represent the most idealistic female empowerment to hit the big screen in a long time. Geena Davis and Susan Sarandon embody a film chock full of female-centric topics but also presenting them in a way that can be accessible by any viewer. One of Ridley Scott’s best films.
#4 – LITTLE MISS SUNSHINE
The breakout hit of 2006, LITTLE MISS SUNSHINE sends a family of kooks on a trip to their wallflower daughter’s beauty pageant. Greg Kinnear and Toni Collette are great, but it was the then rare dramatic turn from Steve Carell and an excellent as always Alan Arkin that led to this being a nominee for Best Picture at the Academy Awards. It also showed that a Volkswagen bus is always a great vehicle for big journeys.
#5 – TOMMY BOY
David Spade has never been better than when he was alongside the late Chris Farley. Farley’s jump from Saturday Night Live to leading man came in the form of the stupid and classic TOMMY BOY. An endearing film that sees Spade and Farley driving to save their dying company, TOMMY BOY has heart along with some really ridiculous sight gags, but it works thanks to the chemistry between the two leads. That and some nice turns from Brian Dennehy, Rob Lowe, and a cameo from Dan Aykroyd.
#6 – FEAR AND LOATHING IN LAS VEGAS
Hunter S. Thompson’s unfilmable book became one of the trippiest films ever made thanks to director Terry Gilliam. Starring a gonzo Johnny Depp and an unrecognizable Benicio Del Toro, FEAR AND LOATHING is a road trip of hallucinatory proportions. From invisible bats to lizard people and a bald cap-sporting Tobey Maguire, this is nightmare fuel and a warning against the dangers of too many drugs.
#7 – STARMAN
One of the most mainstream of John Carpenter’s films, STARMAN is a romantic road movie that blends elements of science fiction with a cross country journey. A major inspiration for this year’s excellent MIDNIGHT SPECIAL, STARMAN is unlike every movie in the genre but yet remains a template for them as well. Jeff Bridges is excellent in the lead role alongside Karen Allen at her best.
#8 – ROAD TRIP
While Tom Green may not be the star he was in 2000, this AMERICAN PIE-esque sex comedy still has some genuinely funny moments of gross out humor. It also kick started an entire generation of college kids who wanted to take an old bus and venture across the country, for better or worse. It also delivers the biggest warning against sending your order back at a dive restaurant in any movie I have seen.
#9 – RAIN MAN
The journey from Cincinnati to Los Angeles in a classic 1949 Buick Roadmaster helps solidify the sibling relationship between Charlie and Raymond Babbitt. Ray’s autism both provokes and endears him to Charlie in what may be one of Tom Cruise’s best performances. As the brothers get closer to each other, we are treated to memorable stops in Las Vegas and other roadside attractions. Definitely one of the best vehicles to conduct a road trip in.
#10 – DUEL
While Dennis Weaver’s character may not be joined by family or friends, his long drive through the California desert is the stuff of road trippers nightmares. Menaced by a big truck with a faceless driver, Weaver is forced to resourcefully find a way to survive. Steven Spielberg’s debut film is a haunting thriller that works four decades later and definitely made me decide against a drive to the West Coast.
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