GIMME FIVE: Road Trip Films

On the Road

There is nothing quite like a good ol’ fashioned road trip. There’s the magical feeling of being free and the enchantment of the endless possibilities of the open road. On the surface, a road trip is about getting from one place to another, but they can be a whole different kind of journey. They can be the catalyst for a life change, the path for self-discovery or the map for future fond memories. I think my old friend Whitey Durham said it best, “The road is long, and in the end, the journey is the destination.”

To commemorate the release of the movie adaptation of Jack Kerouac’s iconic book On The Road, here are five road trip inspired films:

5) Thelma & Louise  (1991)

Road Trip - Thelma

This classic girl power film features Geena Davis and Susan Sarandon as two women that one day decide to break out of their normal life, jump in the car and hit the road. Their journey turns into a womanhunt when Louise kills a man who tries to rape Thelma. They try to escape by heading down to Mexico, while encountering a few extra adventures (cowboy Brad Pitt!) on the way.

4) Sideways (2004)

Road Trip - Sideways

Paul Giamatti plays Miles, an unsuccessful writer and depressed middle school English teacher living in San Diego. Miles decides to take his friend and college roommate Jack (Thomas Haden Church) on a road trip through wine country before Jack ties the knot. Miles wants to have a good time, while Jack wants one last fling. They encounter two women working at a local winery, which provides the basic setup for this dramedy.

3) Little Miss Sunshine  (2006)

Road Trip - Little Miss 2

Sheryl (Toni Collette) is an overworked mother of seven-year-old Olive (Abigail Breslin) and unhappy, sixteen-year-old  Dwayne (Paul Dano). Her husband, Richard (Greg Kinnear), is a struggling motivational speaker and her brother, Frank (Steve Carell), is a gay scholar living with them after a suicide attempt. Also living with them? Richard’s foul-mouthed father, Edwin (Alan Arkin),  who was recently evicted from a retirement home for using heroin. When Olive learns she has qualified for the “Little Miss Sunshine” beauty pageant, the whole family piles in their yellow Volkswagen Microbus for an 800-mile road trip full of quirky family dynamics, car troubles and a lot of laughs.

2) Into The Wild  (2007)

Road Trip - Into the Wild

Based on the true tales of Christopher McCandless, Into the Wild centres on a young man breaking free of society’s reigns and expectations. Christopher (Emile Hirsch) ditches his old life and identity and we follow ‘Alexander Supertramp’ as he travels across America on his way to live in the Alaskan wilderness. This film is beautiful and enchanting with a stellar cast and an incredible soundtrack composed by Eddie Vedder.

1) Away We Go  (2009)

Road Trip - Away We Go 2

Comedy gems Maya Rudolph and John Krasinski play Verona and Burt, a couple in their early thirties who are struggling to meet daily needs and build fulfilling lives as an anatomy artist and an insurance salesman. When they find out they are going to become parents, they are challenged with how and where to raise a child and build a happy family. They embark on an adventure to visit family and friends in hopes of finding the ideal place to settle down.

(Trivia Question: Can you guess which 3 of these films won Academy Awards for Best Screenplay?)

Gimme Five More: Take a ride back into the ’80s with these road trip themed films: Lost In America, The Sure Thing, Rain Man, Midnight Run and Fandango.


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