The 5 Best Road Trip Scenes Of All Time

By Ian MacKenzie On April 17, 2009 · 21 Comments

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From Tommy Boy to Easy Rider, here’s our picks for the road trip scenes that captured the moment and stand the test of time.

The road trip. In the minds of all people, young and old, it conjures up images of neverending highways, new adventures, and the freedom that comes with a full gas tank (or vegetable tank).

Various films throughout the years have tapped into this sense of freedom. Here’s 5 classic road trip scenes that will have you yearning for the open road.

1. Tommy Boy (1995)

The dynamic duo: Chris Farley and David Spade in their best film. While they tried to follow it up the formula with Black Sheep, it lacked the heart of Tommy Boy. In this scene, they’re on their way to sell brake pads to save Farley’s family company. Laughter ensues.

2. Road Trip (2000)

In an interview I read somewhere, director Todd Philips confessed he wanted to make an homage to films like Fast Times At Ridgemont High and Ferris Bueller’s Day Off. (Basically an excuse to show Amy Smart mostly naked).

Yet it’s undeniable the film captures the zest of heading out with your best buddies with little more than a direction and the promise of good times.

3. Dumb And Dumber (1994)

A classic scene in a classic movie. There are so many one-liners from this film still being used today, it rightly stands up as one of the best comedies of the 90′s.

4. Easy Rider (1969)

It’s possible motorcycles sales shot through the roof once these bad-ass opening credits were first shown in theatres. For sheer dripping cool-ness, this scene has yet to be topped. After all, who needs a helmet when you’ve got a handlebar mustache?

5. Good Will Hunting (1997)

“I’ve had to go see about a girl.” With those words, Matt Damon and Ben Affleck cemented their careers for the next 10 years. This final roadtrip scene manages to mist the eyes of even the most emotionless men. SPOILER ALERT: Don’t watch unless you’ve already seen the movie.

How do you like them apples? Any favourite road trip scenes I missed? Share in the comments!

About The Author

Ian MacKenzie

Ian MacKenzie is the founder and former editor of Brave New Traveler. He is a now a contributing editor to Matador, and the network's architect. Ian is also a documentary filmmaker, with his first feature (One Week Job) released in 2010.

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http://www.keepingpaceinjapan.com Turner Wright

Rain Man, Ian – “I’m definitely not wearing my underwear”

http://www.youtube.com/watch?v=AeITXkW0ITs
Travellohr

Hey, Thelma & Louise definitely tapped into a sense of freedom! And, of course, ultimately death. But first, oh, the freedom…
Eva

Ooh, ow, Ian, this list causes me physical pain.

I know, I know, it’s crushingly dull when people get indignant about their entirely subjective picks being left off these lists, but really? 4 of the 5 best Road Trip Scenes of ALL TIME were filmed between 1994 and 2000?

I’ll grant you Easy Rider, and (while I’ve never thought of it as a road trip scene, per se) that Good Will Hunting finale was great.

How about Thelma and Louise? (The finale again [spoilers: http://www.youtube.com/watch?v=4z88U915uq8, or any number of earlier scenes.) Planes Trains and Automobiles has some great ones too, check out the "Mess Around" scene [http://www.youtube.com/watch?v=SOu2PSJ0L10] or again, any number of others.

I’d need to do some digging to come up with specific names and scenes, but surely there were a lot of great road trip flicks being made long before Chris Farley and Jim Carrey came along?

http://www.ianmack.com Ian MacKenzie

Ha, I knew someone was going to call me on the Thelma & Louise. To be honest, I haven’t actually seen it. Therefore, doesn’t make my list! But I do welcome all further suggestions for best road trip scenes.

http://www.collazoprojects.com Julie

Agreed with Turner and Travellohr…. when I saw the title of this article, I immediately thought of the seemingly endless, frustrating, and poignant road trip in “Rain Man,” then of “Thelma and Louise.” I’d also add the road trip scenes in “Motorcycle Diaries” and in “Y Tu Mama Tambien.”
http://www.matadorabroad.com Tim Patterson

I saw Thelma & Louise on a Jet Airways flight over Afghanistan a few weeks ago. Loved it. Sweet and sad, the characters just strong enough to be weak.

But I’m with Ian on the Good Will Hunting clip.
http://oliviagiovetti.wordpress.com Olivia

Little Miss Sunshine takes the cake. Apart from being truly ell oh ell, the scene where (SPOILER ALERT) the son realizes he’s color blind and finally speaks for the first point in the movie with one huge expletive is gloriously moving.
http://www.collazoprojects.com Julie

Olivia- Right on! Totally forgot about “Little Miss Sunshine”– definitely a road trip movie for the age of the dysfunctional family.
http://www.ianmack.com Ian MacKenzie

@ Olivia – I really thought about including Little Miss Sunshine, but I couldn’t find a particular scene on Youtube that I could embed…so it had to be cut.
http://www.truequanimity.com/ Christine Garvin

Gotta admit, these are mostly “dude” movies (though Good Will Hunting can go either way). I had to sit through many a Chris Farley and old-school Adam Sandler movie in high school because of my guy friends–and of course the first one I liked was The Wedding Singer (chick flick, they called it), but I digress…

Thelma and Louise, without a doubt. First one that came to mind.

What about that 80s movie with Bette Midler and the woman from Cheers? Outrageous Fortune, I think? I just remember them jumping from mountain to mountain somewhere like the Grand Canyon. Totally feasible.

And didn’t Britney Spears make a road trip movie??!!
http://www.truequanimity.com/ Christine Garvin

Oh yes, I second Motorcycle Diaries. This makes me want to rent that again…stunning.
http://www.southernhiker.com SouthernHiker.com

While totally a “chick flick” the road trip in the movie ELIZABETH TOWN provides some great inspiration to hop in the car, listen to some tunes from the area’s local artist, and just drive from small town to small town seeing real America. Great post!
Eva

@Christine She did indeed… Crossroads. From what I recall from the trailers, she’s shy and finds herself by singing karaoke in roadside bars. Ha!
http://www.ibackpackcanada.com Corbin

Haha – best list ever! I have got to watch Dumb and Dumber again… “Just go man…”

I agree thoe – motorcycle diaries rocked. Loved when they flipped the bike and Ches buddy is like “is that a dog?!” – awesome. Another great one is “The Art of Travel” – quite a few good travel scenes in it. Mainly the Jungle Crossing through the Darien Gap.
Sandals

I guess the beginning of “Fear and Loathing in Las Vegas” would’ve been too obvious, right?

Then again, not a *typical* road trip movie — except for the bold few who think a pint of raw ether is a travel necessity.

“We can’t stop here! This is bat country!”
DHarbecke

THELMA & LOUISE!!! THELMA & LOUISE!!!

Oh, wait – I’m a man. Never mind.

But seriously! How about Lost in America, or Something Wild? Or… best of all…

The Muppet Movie. There. I said it. The Muppet Movie.

Huh. I’m still not being serious…
http://matadorabroad.com Tim Patterson

Arg, Elizabethtown was absolutely horrible. And not because it was a chick flick. Because the script was awful.
Eva

@DHarbecke While we’re talking muppet-related flicks, I’m gonna have to follow suit and nominate “Follow That Bird”!
DHarbecke

Elizabethtown would have been better with an all-Muppet cast…
http://www.roughguides.com Ben

For my money, something from the unsettlingly beautiful Badlands (Terence Mallick, 1973) has got to be in there.
http://www.planning-fun-road-trips.com TaraTravels

I can’t believe that no one thought of THE road trip movie of the ages: National Lampoon’s Vacation! There is no movie out there that captures the weirdness and boredom and everything else that is a road trip better – especially in terms of a family road trip. Who can forget Aunt Edna and her vicious dog, the rip-off mechanics who happen to also be the sheriff and deputy of the town, and Christy Brinkley in that hotrod?

The 5 Best Road Trip Scenes Of All Time

1. Tommy Boy (1995)

2. Road Trip (2000)

3. Dumb And Dumber (1994)

4. Easy Rider (1969)

5. Good Will Hunting (1997)

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