On The Road Again ( Top Five Road Trip Movies )

So, as some of you may recall, this past Saturday I claimed I felt like this…


That was because I knew my brother and I would be on our way back from Lord-knows-where after taking a road trip together to celebrate my upcoming wedding. Well, for those of you who might be curious, it turns out I actually felt more like this…


As a big ‘ol Red Sox fan myself, this was like making a pilgrimage to the holy land. I was absolutely floored to be back in Boston, be sitting in Fenway Park, and that everybody involved in pulling off this caper managed to keep it a surprise. Not to get too far off on a warm and fuzzy tangent, but I’m a pretty lucky guy to be surrounded by such wonderful friends and family – my younger bro in particualr.

So with the roar of the Fenway faithful still ringing in my ears, and the smell of clam chowder still in my nose, I figured this would be an opportune time to take a look, albeit a somewhat abbreviated one, at some cinematic journeys that could rival our trip to Beantown. Please read on for…

Hatter’s Top Five Road Trip Movies

#5. SIDEWAYS (2004)… However on our trip, the groom-to-be did not attempt one last fling before settling down, nor did he make it a mission to get his best man laid. I am surprised that we drank as little as we did though.

#4. EASY RIDER (1969)… However on our trip, we weren’t seen as quite the outsiders. Plus, I look pretty dumb in leather.

#3. THE MOTORCYCLE DIARIES (2004)… However on our trip, nobody was witness to either traveler showing signs of being a future revolutionary. Likewise, both travelers knew the difference between a mambo and a tango.

#2. PLANES, TRAINS, AND AUTOMOBILES (1987)… However on our trip, there was no moment of believing one’s hand was between two pillows.

#1. THE MUPPET MOVIE (1979)… However on our trip, we didn’t drive around in a Studebaker. I will admit that many of my jokes are about as good as Fozzie’s, and that younger bro has moments of grumpiness like Sam the American Eagle. But the heart and soul of this trip was taking a journey together worthy of The Rainbow Connection…thus this Henson classic lands on the top of my list.

Did I miss one? Feel free to leave comments naming your favorite road movies, along with suggestions for the next top five.

23 Replies to “On The Road Again ( Top Five Road Trip Movies )

  1. Gotta throw out Vacation as a long shot for my top 5 just on pure memories sake. Oh, and because I'm a sucker, The Blues Brothers would be a most definite requirement! 🙂 Great list though, can't really argue with any choice.

  2. Aw what a nice surprise! I'm sorry the Boston weather has been sort of crappy lately- all rainy and humid all of the time.

    I would probably have The Blues Brothers as well. And Smokey and the Bandit!

  3. @ Tony… Good call, but lordy has it ever been ages since I've watched that one.

    @ Univarn… No long shot there, that's a classic.

    @ Alex… The weather on Friday was perfect! Sunny and cool during the day, not too cold for the game that night. Saturday it poured though, which didn't stop us from wandering around Harvard…but certainly made for some squishy shoes.

    @ Aiden… I can't say why, but I've never really seen THE BLUES BROTHERS as a road movie. Interestingly though, the last time I made a top five in honour of a ballpark trip Jake and Elwood made the cut. That was my Chicago Movies Five.

  4. Planes, Trains & Automobiles is easily one of my favorite comedies of all time. Classic piece of work.

  5. I really miss Baseball. The channel that has shown it for the last ten years in England stopped after last season. We had a brief reprieve when ESPN was broadcast for a couple of months in the summer but now nothing again.

    Good call on the Motorcycle Diaries and great film as is Easy Rider. Here are a few other suggestions for you:

    Fandango
    Two Lane Blacktop
    Vanishing Point
    Little Miss Sunshine
    Midnight Run
    Into the Wild

    I agree on the Blues Brothers not being a Road Movie. Smoky and the Bandit is more a chase movie.

  6. @ Danger… Isn't it more politically correct to now call it Harold and Special White House Advisor Kumar Go to Whitecastle?

    @ Joel… I'm ashamed to admit I've never seen Logo. Mock me if you must.

    @ Fandango… I didn't know many Brits even liked baseball! If you ever make it to Toronto, I'll personally get you to a game.

    INTO THE WILD is a great suggestion, though my opinion of it has somewhat soured knowing that the actual guy shouldn't have been in the spot he gets into.

  7. Baseball isn’t that popular over here but does have a reasonable following; at least it did until the coverage stopped. I know there has been a bit of a campaign to get it back so another channel my pick it up. I have been watching on and off on TV for years. I have only ever been to one game. San Francisco V Arizona but will defiantly go again next time I am in America. I will take you up on that offer if I get as far as Toronto. My favourite sport is actually football (I assume you call it soccer the same as they do in America) I live 20 minutes drive from my teams stadium so get to go a lot.

    Although I really enjoyed into the wild, I do see it differently now I have read the book and know more of that happened to him and why.

    Daniel. Good call, I had forgotten Y Tu Mama

    (Hope this works. It isn’t accepting my wordpress id. This is my google one. Andy aka FandangoGroovers.)

  8. @ Daniel… TAMBIAN just missed the cut for me, but that's definitely one of the all-time best.

    "Hey Chewie – To our mothers!!"

    @ Andy/Fandango… it's a shame when that happens to a movie, isn't it?

    PS – Which football club do you follow?

  9. Easy Rider is surprisingly fun,oh, except for that part at the end where our most lovable hero (for me, Nicholson) is just learning to breathe free when he gets his brains bashed in by the downhome troglodytes, and Peter Fonda and Dennis Hopper end up with shotgun holes in their chests that you could shove an engine block into…I only watch it when I'm feeling strong. Sideways is a much gentler ride, has some funny-as-hell moments, and thank God Paul Giamatti does finally bust out and drink that rare wine he's been hoarding–even if it is with a Whopper.

  10. Interesting list. I like how you incorporated your own road trip into it all. As I read through it I realized there was one amazing road trip movie you are missing. That's because it doesn't readily come to mind as a road trip movie: Dumb and Dumber. But hey, they are traveling across the country and it is HILARIOUS.

  11. @ Margaret… Never said it was a feel good movie. Actually, I'm somewhat known for being the guy who likes watching the heavier stuff…my "sick day movies" are flicks like NO COUNTRY FOR OLD MEN and CHINATOWN.

    @ That Show… Weird thing, I've never really been a fan of D&D. Might just be that I waited too long to see it, and by then it wasn't living up to how funny I'd been told it was. Strangely it just isn't my cup of tea.

  12. Oh, your lists are inspiring. I like people who write about movies and make lists… adding you.

  13. I second Thelma and Louise and have to say I love Shag, the Movie. Still find it funny seeing Phoebe Cates, Annabeth Gish and Bridget Fonda grown up.

  14. @ Miss Topanga… Glad I can impress. Thanks for reading! (PS, How did you happen upon my humble blog?).

    @ Ross… Holy Schnickie!! That one brings me back!!!

    @ Jess… My bride-to-be would LOVE you, since she's long been trying to get me to sit down with her and watch SHAG. I did as a kid, didn't dig it much…thus I'm in no hurry. But good call!

  15. I'd have to throw in the chick-ier road trip flicks for my own list, including the aforementioned Thelma and Louise, Boys on the Side and Camilla.

    – Sue

  16. @ Soo-See… Can't say I'm with ya when it comes to CAMILLA or BOYS ON THE SIDE, but THELMA & LOUISE I sure do dig.

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