10 Memorable Road Trips in Hollywood History

(This article originally appeared in the now-defunct Retrofied magazine.)

By Steve Spears

Will we ever truly tire of the Hollywood genre of the Great American Road Trip Movie? From 1934’s “It Happened One Night” to 1969’s “Easy Rider” to 2020’s “Nomadland,” cinema has always celebrated wanderlust. 

For those of us who spent our formative years in the ‘70s and ‘80s, we are rich with quality options to partake of when battling off a sense of pandemic-laden cabin fever. Still, the very best road movies typically had a trophy at the end – be it literal (as in “Cannonball Run”), professional (I’m talking about you “Almost Famous”) or even metaphysical (that’s the best I can do for the kitschy “Highlander.”)

If chasing the prize really drives you, these movies will have you slamming the petal to the metal. You might think the list starts and ends with Burt Reynolds and Sally Field in a black Trans-Am … okay you’re about half-right, but stay with me because these are all classics in their own unique way. Here are the road trip movies – listed chronologically (as the American Automobile Association would have intended) – that have us yearning for a spell on the blacktop. 

Burt Reynolds in “Smokey and the Bandit.” (Publicity photo)

SMOKEY AND THE BANDIT (1977): Can you even conceive what theater box offices were like before the blockbusters “Star Wars,” “Close Encounters of the Third Kind” and “Smokey and the Bandit” arrived? Crickets. If you’re forgotten the plot – basically Burt Reynolds and Jerry Reed are hired to bring back a truck full of Coors beer to Atlanta in time for a victory celebration at a local racetrack – but they encounter a vengeful Sheriff Buford T. Justice (played with zeal by the legendary Jackie Gleason) along the way. What began as a beer run now more closely resembles a “Mad Max” movie. Reynolds met the love of his life – Sally Field – while the rest of us met the love of our teenage lives – a Pontiac Trans-Am.

Bill Murray as Hunter S. Thompson (Publicity photo)

WHERE THE BUFFALO ROAM (1980): I sense a lot of quizzical looks out there. Give this movie a chance! Fresh off of “Meatballs,” Bill Murray plays legendary “gonzo” scribe Hunter S. Thompson is this cinematic montage of the writer’s greatest road stories – “Fear and Loathing in Las Vegas,” “Fear and Loathing on the Campaign Trail,” “The Great Shark Hunt,” you name it. The late Peter Boyle plays his travel partner and attorney Carl Lazlo. Together they must dodge all the obstacles – half-clothed nurses, lusty media pools, cases of alcohol – to get their story to a magazine publisher on time. Enjoy the wickedly smart appearances by Bruno Kirby, René Auberjonois and even Craig T. Nelson as a dope-fighting cop. Murray and Thompson would become lifelong friends after the filming ended, because of course they did.

Burt Reynolds and Dom DeLuise in “Cannonball Run.” (Publicity photo)

CANNONBALL RUN (1981): Imagine “Smokey and the Bandit” with a bigger ensemble cast and a lesser script. Ouch! It’s “Cannonball Run!” (Oh, hush, it’s still a classic.) Based on an actual “outlaw” coast-to-coast road race, this movie starred – take a deep breath before reading –  Burt Reynolds, Dom DeLuise, Roger Moore, Farrah Fawcett, Jackie Chan, Jamie Farr, Mel Tillis, Terry Bradshaw, Peter Fonda, Adrienne Barbeau and Dean Martin. It’s probably best known today for showing movie bloopers during the closing credits.

Chevy Chase as Clark Griswold. (Publicity photo)

NATIONAL LAMPOON’S VACATION (1983): If you worshipped John Hughes in the ’80s, you should know that he wrote the screenplay for the first “Vacation” movie before writing any of his teen classics. It’s based on a short story he wrote for “National Lampoon” magazine, which was published in 1979. In it, Hughes recounts a family vacation from his youth that went horribly wrong. (How close to the movie is the story? Here’s the first line: “If Dad hadn’t shot Walt Disney in the leg, it would have been our best vacation ever!”) In our beloved movie version, the finish line of the adventure is Wally World (if only the moose outside had told us it was closed for cleaning.) Say what you like about the subsequent sequels – I loved them all – “Vacation” is probably forever the prototypical road movie of the 20th century.

Don’t lose your head during a road trip. (Publicity image)

HIGHLANDER (1986): The prize in this movie is literally “the prize” – I don’t want to ruin any more for those who haven’t yet partaken. A group of immortals from throughout history engage in hand-to-hand combat – they can only die if their heads are chopped off – until a time (and I quote from the late Sean Connery) “when only a few of us are left, we will feel an irresistible pull towards a far away land… to fight for the prize.” (And yes, of course, the far away land is New York City. This was the ‘80s after all! Sorry, no Pandora yet.) The movie would spawn a slew of sequels and a TV series as well as the career of future Shawshank prison guard and SpongeBob crustacean Clancy Brown. Still not convinced you need to watch it? Queen handles the soundtrack. 

Wonder why they call him ?Hawk? (Publicity photo)

OVER THE TOP (1987): Expanding on the “it was worth it for the music” argument from “Highlander,” I give you this weak cup of coffee. Sylvester Stallone plays Lincoln Hawk – worst screen name ever after Johnny Utah – who takes his alienated and resentful son on the road to Las Vegas to compete in … an arm-wrestling tournament? There’s a dying mom (Susan Blakely), a vindictive father-in-law (Robert Loggia) and more cameos from professional arm wrestlers – it’s a thing – than any movie since the dawn of time. But dance music divinity Giorgio Moroder handles the score, and Kenny Loggins sings a power ballad that will have you weeping as the credits roll. 

David Spade and Chris Farley in “Tommy Boy.” (Publicity photo)

TOMMY BOY (1995): Chris Farley plays the underachieving son of an autoparts magnate (Brian Dennehy), who must go on the road and sell enough parts to save the family business. If you’ve seen this movie, you can probably quote at least 50 lines from it. More importantly, “Tommy Boy” proves several important cinematic theorems: Farley and his characters drip with sincerity (“Brothers don’t shake hands. Brothers gotta hug.”), Rob Lowe has impressive comic chops, and Bo Derek can act – no, I’m just kidding. (The late film critic Roger Ebert has this flick listed among his “most hated” list.) BTW, if you never thought of “Come on, Eileen” by Dexy’s Midnight Runners as a road trip song, you will after seeing “Tommy Boy.”

The “Tiny Dancer” singalong scene during “Almost Famous.” (Publicity photo)

ALMOST FAMOUS (2000): Screenwriting god Cameron Crowe spins a story of a teenage rock critic in over his head after being tasked with covering an up-and-coming band on the road and getting the final story to Rolling Stone by publication date. Sound pedestrian? Hardly. Every role is blessed with an actor at his or her start toward the apex of thespian perfection –  Kate Hudson, Billy Crudup, Jason Lee, Frances McDormand, Philip Seymour Hoffman, Anna Paqui. And it’s all woven together masterfully with music by Nancy Wilson (then Crowe’s wife). Based on his actual experience at “Rolling Stone” covering bands such as the Allman Brothers Band, Led Zeppelin and Lynyrd Skynyrd, Crowe won an Oscar for best screenplay. It won’t be the only film of his on my list.

Love it or hate it, “Elizabethtown” is still an amazing movie about embracing failure and grief. (Publicity photo)

ELIZABETHTOWN (2005): Well, hello again, Cameron Crowe. Fans of his are divided on this offering – one of my personal favorites – which was attacked by critics disappointed by the perceived “tone deaf” and “sketchily conceived” aspects of it. The story features an athletic shoe designer named Drew (Orlando Bloom at the height of his popularity) who is consumed with the difference between failure and a fiasco after one of his designs becomes a global laughing stock. Prepared to commit suicide, he is momentarily saved upon learning his father has unexpectedly died while visiting family in Elizabethtown, Kentucky. On his journey to bring his father’s body home, he meets an angelic flight attendant (Kirsten Dunst), who guides him through the grief – and the famously confusing Kentucky highways – before setting Drew adrift on a road trip to find his way – and his self – home.  A decade after it debuted, Crowe proudly defended it, calling it “a tip of the hat to tradition, to family heroes, and to those roller-coaster summers when life shows itself in all its indelible pain and glory.” 

A dark comedy for sure, “Little Miss Sunshine” has still captured the essence of a road trip. (Publicity photo)

LITTLE MISS SUNSHINE (2006): If you were expecting a load of laughs from this road adventure because it starred Steve Carell, Greg Kinnear and the late Alan Arkin, then you probably left the theater before the movie got really good. When the youngest daughter of the remarkably dysfunctional of a New Mexican family qualifies for a children’s beauty pageant in California, the tribe sets off on a road trip that will predictably be plagued by mechanical, personal and professional breakdowns. Thankfully it’s nothing that an adolescent striptease to “Super Freak” can’t solve. See? Sometimes it’s really just about the music.