Top 10 Two People Buddy Road Trip Films

Neal Damiano heads to the highway to sample some of the best buddy road trip movies including Something Wild, Planes, Trains & Automobiles and Midnight Run.

10. Harold & Kumar Go to White Castle (Leiner, 2004)

Harold and Kumar Go To White Castle - Top 10 FilmsA stoner comedy of epic proportions starring John Cho and Kal Penn, the two title characters go on an adventure to satisfy an insatiable craving for White Castle burgers. The mission is quite simple – drive on over to White Castle – but these two stoners can’t seem to get out of their own way. Nothing is going to stop the two from satisfying the weed munchies with those classic mini burgers. They ride a cheetah. Their car is stolen by Neil Patrick Harris. It’s all good fun.

9. Tommy Boy (Segal, 1995)

Tommy Boy - Top 10 FilmsA lot of comedies are funny but not well written stories. Tommy Boy is an exception, if you took the comedy out of Tommy Boy it’s still a compelling story and that is quite unique. The chemistry between David Spade and Chris Farley is undeniable – the odd couple routine just works perfect here. David Spade’s character looks after Chris Farley as if he’s a child and in many ways Farley’s character is a child unable to take care of himself. Spade has an admirable respect for Mr Callahan with an endearing heart and promises to care for Tommy on their road trip.

8. Easy Rider (Hopper, 1969)

Top 10 Films of Dennis Hopper - Easy RiderEasy Rider broke boundaries in film, shunning conventional ways. Despite no support from the Hollywood studios and a major backlash from the industry, Dennis Hopper and Peter Fonda went on to make the ultimate road trip film. Hopper and Fonda are two individuals living on the fringes of society. Armed with their motorcycle and backpacks they take to the road on a destination to Mardi Gras. Easy Rider has some of the most fascinating and vibrant moments – for example, the graveyard scene comes to mind. The use of camera, color, and lighting is incredible. With the exception of a very sad ending, Easy Rider is an amazing adventure on the open road from start to finish.

7. Thelma & Louise (Scott, 1991)

Thelma and Louise, Girl Power, film, Ridley Scott - Top 10 FilmsHow about the ladies get their due and have a little fun outrunning the cops? While most of the movies on this list feature male buddies teaming up, this 1991 classic joined Susan Sarandon and Geena Davis as the famous outlaw partners. While simply looking for a break from routine and the cumbersome of their relationships, their fun goes south and they end up on the run from the law. It also introduced us to a young Brad Pitt, who has gone on to make some amazing films. Although the ending is incredibly sad in a victorious kind of way because you’re cheering for these two “badasses” the whole film. It’s a bittersweet ending, I don’t think Thelma or Louise would have it any other way.

6. Sideways (Payne, 2004)

Sideways - Top 10 FilmsA quintessential road trip film. Two middle-aged friends, disappointed with their place in life, go soul-searching and drinking around California’s wine country. Paul Giamatti plays a stumbling writer, while Thomas Haden Church plays a struggling actor that almost no one seems to recognize. They have an awkward but interesting chemistry through the movie. Thomas Haden Church is very entertaining as a smooth talking playboy and earned an Oscar nomination for Best Performance in a Supporting Role in Sideways. I feel he’s a very underrated actor. Paul Giamatti’s performance is outstanding and so human. His disappointment radiates through the screen and it’s an interesting contrast to Haden’s easy going nature. A very well written character-centered film.

5. The Sure Thing (Reiner, 1985)

Top 10 Films of John Cusack - The Sure ThingThe Sure Thing is one of my favorite films made in the eighties simply for the insane sexual tension between the two central characters played by John Cusack and Daphne Zuniga. Two college students forced by circumstances to travel cross country together. The contrast of Cusack’s goofyness and Daphne Zuniga’s strait-laced demeanor is funny to watch. On the surface they can’t stand each other, but the sexual tension is obvious and very comical. The build up of a love / hate battle brewing in the atmoshpere is so thick you can cut it with a knife. The more obnoxious Cusacks character is the more Zuniga likes him. But this sassy over- achiever will never admit it.

4. Rain Man (Levinson, 1988)

Rain Man - Top 10 FilmsI’m not a huge Barry Levinson fan but Rain Man is an exceptional film. Cruise plays Charlie, a cocky and self-centered jetsetter only concerned about fast cars and beautiful women. Charlie gets the rug swept out from underneath him when he finds out he has a long lost brother with autism. When Charlie realizes his late fathers will is left to Raymond. He sets out to find Raymond and act as his legal guardian. At first the motives are pure selfish and greed. As Charlie spends time with him developing a relationship he realizes there is more important things in life than money. The film truely has memorable quotes and iconic scenes.

3. Midnight Run (Brest, 1988)

Charles Grodin, Robert De Niro, Midnight Run, Martin Brest, Beverly Hills Cop - Top 10 FilmsHow’s this for a storyline – an ex-cop turned bounty hunter is hired to capture a crooked accountant who steals a large amount of money from the mob. Midnight Run is a madcap, hilarious, fun ride. The pairing of De Niro and Grodin is almost too perfect. Mixing the grumpy demeanor of De Niro with the careless leisure of Grodin is pure brilliance creating a unique dynamic between the two. They argue back and forth like an old married couple. Both encounter their own personal fears together along the trip for example flying and swimming. Although not buddies in the conventional sense they do begin to respect each other. De Niro admiring the balls it took for Grodin to say screw the system. Grodin respecting him for choosing friendship over money.

2. Planes, Trains & Automobiles (Hughes, 1987)

Del Griffith, John Candy, Planes Trains and Automobiles, 1980s Comedy Film Characters - Top 10 FilmsThe ultimate Oscar and Felix homage, John Candy and Steve Martin play polar opposites traveling together over the Thanksgiving holiday. John Hughes wrote and directed an incredibly funny and entertaining road trip film. Steve Martin plays an uptight businessman, who is just trying to get home to his family for Thanksgiving. Due to a few unfortunate happenings he hooks up with an unlikely travel mate. John Candy plays a kind hearted aimless drifter who talks way too much. Undoubtedly, Candy gets on his nerves to no end but Martin’s character has a soft spot for the man. Obviously, what makes the film is the dynamic between Martin and Candy but it’s also a really good story – humorous, engaging, and at points sad. Hughes doesn’t defer from the fact that they care for each other.

1. Something Wild (Demme, 1986)

Something Wild - Top 10 FilmsThis is one of my favorite films because of the amazing chemistry between Melanie Griffith and Jeff Daniels. Jonathan Demme directed a highly entertaining adventure of two complete opposites on a chance meeting finding love. Melanie Griffith gives Lulu a free spirit, who lives life with no restrictions. Daniels plays the opposite – a well mannered professional. One morning Daniels decides to catch a thrill by skipping on a breakfast bill. Lulu happens to be in the same diner and spots him out. The character of Lulu really makes the film because Griffith delivers this uncanny ability to bring out the wild side in anyone. Lulu takes him on a much needed adventure swaying him so far away from his conventional structured ways. In the process Daniels realizes it’s quite fun and liberating to just let go. I enjoy these kind of films because the central characters learn so much from each other along the way. An absolutely thrilling and fun ride. I’m so glad the film is released on Criterion, well deserving.

Written and Compiled by Neal Damiano

Tell us: what are your top 10 buddy road trip films?

More Top 10s you might like:
Top 10 1980s Comedy Characters | Top 10 Films Featuring Terror On The Highway | Top 10 Road Trip Comedy Films | Top 10 Car Chases of All Time | Top 10 Buddy Films since 1980

About the Author
Neal Damiano calls himself “an unhip film geek” who mixes his passion for movies with an enthusiasm for travel, music and journalism.

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  1. Avatar
    Callum Reply

    Some great films in this category. I guess I love two people road trip movies.

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    Rodney Reply

    Sideways, now there was a hugely entertaining film.some nice choices here Neal!

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    CineGirl Reply

    Yeah, Sideways is brill. As are so many on here. Midnight Run is endless fun.

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    Tarka Reply

    Sideways is one of my favorite movies. I love Something Wild too.

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    tHoward Reply

    My favorite movie of all time is The Last Detail which is the ultimate buddy road trip movie. Unfortunately it has three main stars, not two. I have to say that this list is great though, many brilliant films and a number one that I haven’t seen. Thanks for the recommendation Neal.

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    aman Reply

    hands down ‘sideways’. The writing is just insane.

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    Honor Knight Reply

    Midnight Run. Nuff said. 😉

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    Quaid Man Reply

    midnight run gets my vote.

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    ArchE Reply

    I’m in my Ferrari trying to catch up Neal, put the brakes on my friend. Excellent list by the way – some real cinematic delights right here.

    There are a few two-person road trips I like – Harry and Tonto if a man and his cat counts, Paper Moon and Sullivan’s Travels would all be worthy additions (in a top 13). But I’m not sure what you’d cross off the top 10 to get them in.

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    Neal Damiano Reply

    Thanks for the read, guys. I thought there would be more love for Trains, Planes, and Automobiles? Such a great Hughes film!!

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    Janet Reply

    Really good list Neal. I love Planes, Trains and Automobiles but my favorite is Midnight Run. Just love the crime caper feel of the story.

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    Dan Reply

    Really enjoyed reading through this top 10 Neal. I’ve looked at buddy and road trip films before on the site but not as one. It’s interesting but not surprising how these narrative traits work so well together.

    I think Planes, Trains and Automobiles is the obvious one. It’s such a great story with two lovable characters. But I also love Something Wild, a film that seems to pass under the radar a bit. Melanie Griffith is fantastic in that film – it’s my favourite performance from her as she has that sexy, femme fatale thing going on and it works so well against Jeff Daniels’ suited, shy city-dwelling “do-gooder”.

    Midnight Run is another favourite of mine, De Niro and Grodin work so well together, a bit like Planes, Trains and Automobiles. Great use of the “journey” to create that sense of adventure and the building of friendship.

    Of the other films featured – Sideways is an all-time favourite of mine. I love everything Alexander Payne has done but Sideways with its Californian wine country setting and Paul Giamatti on acerbic top form, there’s nothing not to love about the film.

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    Dan Grant Reply

    Terrific idea for a top ten Neal. Planes Trains…would be my number one and number two would be The Sure Thing. We both share a love for 80’s films, especially the high school/college kind. The Sure Thing is imo, an under rated gem. Reiner, as I’m sure you know, has said that Cusack brought so much to the character and had so many ideas that Reiner just let him run with it. “You have a credit card?…..Oh, but my father told me only to use it in case of an emergency……maybe one will come up.”

    I’m kind of ashamed to say I have never seen Something Wild. It was always one of those films I always wanted to rent from the video store, but never got around to it. I guess I’ll have to check it out if it has your seal of approval.

    Great job with this top ten, Neal.

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    Dan Grant Reply

    Oh, and Sideways is one of my faves as well.

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    Dan Grant Reply

    Sorry, I should have put all these comments in one post lol, but Planes Trains is so good on so many levels. I’m not sure I have laughed as hard as I did in PTA when Martin goes to the car rental company and fires off his diatribe using the F-word in all it’s glory. For a John Hughes film, it was quite shocking.

    I love your article bud. 🙂

    • Avatar
      Dan Reply

      Totally agree. There are few times I’ve laughed so hard, and for as long, as when Steve Martin riffs on the F-work during his expletive-ridden recollection of what he’s just been through to get there.

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    Dan Grant Reply

    Yep, so we feel the same way Dan.

    May I see your rental agreement?
    I threw it away.
    Oh boy.
    Oh boy what?
    You’re F*****!

  17. Avatar
    Derek Reply

    Put me down as another fan of Planes, Trains… Love these buddy road movies.

  18. Avatar
    Neal Damiano Reply

    @Dan Grant
    You must see “Something Wild” its a fun ride!!

  19. Avatar
    Dan Reply

    Something Wild should be at the top of your to-see list now Dan. Great film.

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    Lemony Reply

    surprised to see Harold and Humar on here but otherwise, great list.

  21. Avatar
    Neal Damiano Reply

    Thanks for reading and the input.
    I’m interested to know why surprised??
    Harold and Kumar Go to White Castle is a very funny, entertaining film.
    I laughed when I watched it and that’s why I put it on the list at #10.
    My lists are diverse I like it that way.

    • Avatar
      Lemony Reply

      It’s the best of the Harold and Kumar films, I’ll give you that.

      • Avatar
        Neal Damiano Reply

        Alright, thanks Lemony,

        When you watched the film, did it make you laugh??

        • Avatar
          Lemony Reply

          Yeah, there were a few laughs, it’s just next to the others on this list it feels like the odd one out. All the rest are such classics (even Sideways which came out the same year) but Harold and Kumar feels insignificant in comparison.

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    Dan Grant Reply

    I actually thought the sequel for HAK was funnier than the first. But I do think the original has a place on the list for sure.

    • Avatar
      Neal Damiano Reply

      @Dan Grant,

      Escape from Guantanamo Bay was very funny!

  23. Avatar
    Neal Damiano Reply

    I got you, but I have to keep it well rounded.
    Thanks for the feedback!

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