5 Best Road Trip Movies

5 Best Road Trip Movies

5 Best Road Trip Movies

It’s been said that it is the journey, not the destination, that is most important. Never has this been truer than in the case of road trips. Road trips, when done well, are one of God’s greatest gifts. The open road, the freedom that comes with said open road and the snacks are all great, but they’re not what makes road trips truly memorable. The thing that makes road trips worth remembering are the people you go on these trips with. Sometimes, a simple road trip can reconnect a brother and sister who have long been estranged. Other times, lifelong friendships can be formed on those deserted highways. There’s just something about being in a car for 5-10 hours that really brings people closer together. Hollywood knows this and has produced a myriad of “road trip movies” focusing on the relationships established because of those trips. And no, we’re not talking about the actual movie “Road Trip.” That movie was garbage. No, we’re talking about the films that made us want to jump in the car right after seeing them.

5) Detroit Rock City (1999)

5 Best Road Trip Movies

There is truly nothing better than you and a bunch of your friends cramming into a car to drive to a concert. The excitement is in the air and the possibilities are endless, especially if you just broke out one of your friends from a Catholic school and you’re going to see the Greatest Band in the World, KISS. That’s the premise of the 1999 film Detroit Rock City and, really, it’s all the information you need. It’s a bunch of kids getting in trouble on their way to a rock show. We’ve all been there. I mean, maybe we haven’t been mugged by an 11-year-old or hooked up in a confessional, but still. We’ve all desperately wanted to see our favorite band play and would stop at nothing to get there. The Detroit Rock City crew took that to the extreme in their pursuit of KISS and, in doing so, they cemented their friendship and made new friends as well.

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4) Sideways (2004)

5 Best Road Trip Movies

Of course, sometimes the best road trips are shared between just two people. This is what happened with Miles and Jack (Paul Giamatti and Thomas Hayden Church), two best friends who are embarking on a week-long bachelor trip through the California wine country. Miles wants to show Jack, the groom, a week of golf, food and especially wine. Jack just wants to get laid before he gets married. Yeah, Jack kinda sucks. Anyway, Miles and Jack go on an adventure together that sees them fall in love with a couple women, get kicked out of a wine tasting, get beaten up by one of the aforementioned women and more. It’s truly a comedy of errors caused by wine drunkenness and it’s the bachelor party we’ve wanted to go on ever since we saw the film. We didn’t know how much we liked wine before we saw Sideways.

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3)  About Schmidt (2002)

5 Best Road Trip Movies

Road trips don’t have to include a bunch of people. Sometimes, they can include just one person who is trying to find himself and needs the open road to do it. That is what happened in the 2002 film About Schmidt, starring Jack Nicholson. After the sudden death of his wife, and his own retirement, Warren Schmidt goes on a cross-country jaunt to stop his daughter’s wedding. While on this journey of self-discovery, Schmidt finds out that forgiveness is important, not only for those who need to be forgiven, but also for those who need to forgive. Schmidt is not a happy man. He was bored with life and he needed something to draw him out of his funk. The road trip to Denver he took did just that and, while he may not have found himself right away, he did eventually come to accept his wife’s death, his daughter’s marriage, and his own mistakes.

2) Dumb and Dumber (1994)

5 Best Road Trip Movies

Dumb and Dumber has the ultimate road trip movie premise: two best friends travel across the country to find the girl that one of them loves. Has there ever been a better reason to go on a road trip? We think not. That is just one of the reasons why Dumb and Dumber was such a huge hit back in 1994. Another reason was because Jim Carrey and Jeff Daniels are hilarious. Harry and Lloyd are not what you would call…smart. But they’re lovable and they make us laugh. When Lloyd Christmas decides to track down the woman he had instantly fallen in love with, the two decide to hop in Harry’s van and travel to a little place called Assssspeeennnn. The journey there both tests and cements their friendship. It’s also the journey that introduced them to a hit man who wants to kill them for accidentally stealing a briefcase full of money. And then they accidentally kill him. And then they accidentally make a police officer drink a bottle of their own urine. It makes sense in context. The point is, Dumb and Dumber is the perfect road trip movie to watch with your best friend, right before taking a trip yourself.

1) Planes, Trains and Automobiles (1987)

5 Best Road Trip Movies

The entries in this article have focused on road trips between friends and ones of quiet introspection with one’s self. But what happens when you’re forced into a road trip with a complete stranger who also happens to be the most annoying person you’ve ever met? Such is the case with Planes, Trains and Automobiles, a 1987 John Hughes film starring Steve Martin and the late, great John Candy. Neal Page (Martin) is trying his hardest to make it back home for Thanksgiving, but a chance encounter with Del Griffith (Candy) throws all of his plans into disarray. The end result is the two of them traveling back to Chicago together, via, well, read the headline. This is the perfect odd couple pairing. It’s also the perfect road trip movie because it shows just how powerful a 2-day drive with somebody really is. Page hated Griffith at the beginning of the film but, by the end, they’re almost even friends!

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Weekend: Oct. 24, 2019, Oct. 27, 2019

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