Elizabethtown (2005): Failing Big and Sticking Around

An uplifting scene about not being ashamed after going all in and failing

Elizabethtown (2005) followed me around on DVD from high school through college, and I just got around to watching it yesterday when I saw it on Prime. “Did you see Lost in Translation,” I would ask my friend in high school who became my college roommate. “Not yet,” he would say, “but I really like Elizabethtown.”

He also liked Eternal Sunshine of the Spotless Mind (2004). Now that I think of it, he probably had a crush on Kirsten Dunst who’s in these movies that were always somewhere close. If the DVDs were not in his bedroom, they were on the “entertainment” stand that we and every other college kid had who went dorm room shopping with their mom at Target.

I think I put off watching Elizabethtown because it seemed too nice of a movie at the time. When it started following me, I was watching very dramatic films like Thirteen (2003), Crash (2004), and Mulholland Drive (2001) — movies I have no taste for today.

Can you believe that when a college crush came over for the first time I put in Thirteen, even when the happy picture of Orlando Bloom giving Kirsten Dunst a piggyback on the DVD cover of Elizabethtown was staring me in the face? Yup, I did that. Instead of spooning on the couch to a romance, we watched a sweet thirteen-year-old girl become addicted to drugs and sex. My crush didn’t seem to mind though. She was actually quite engaged, pausing the movie every twenty minutes to reflect on how certain scenes related to her life. What could have been annoying was actually quite special — she was engaging with a movie like I’d never seen before.

Why did I gravitate toward these movies filled with distressed characters rather than movies like Elizabethtown with wholesome characters like Claire played by Kirsten Dunst? A character who, at the end of the movie, creates mixtapes and maps for her love interest’s road trip and expects nothing in return? I think a few reasons:

1. My childhood was fun and the concept of not having fun through these weird things called stress, anxiety, and depression interested me.

2. When I started experiencing some of these weird things myself, hard-time characters kept me company.

3. The movies were entertaining. But I’ve realized in the past few years that entertainment through dramatic suffering comes at a cost.

The foulness of those wonderful films have crept up on me throughout the years. Not individually but in aggregate. Unfortunately, I think it’s true about what moms say about violent games and movies rotting your mind. But that’s what I was attracted to and, fortunately, I balanced them out with movies that are sweet and good. Life is sweet and good. Rough at times, but sweet and good. That’s what Elizabethtown is.

Like some of the director’s other films including Jerry McGuire (1996), Elizabethtown is a hopeful movie about relationships. Though it takes some time to gain steam, it inspired me to write a letter to a girl I’m seeing and adore. However, like Kirsten Dunst’s character (Claire), I feel like a “substitute” in the relationship. I feel like I’m substituted into her life, not part of it.

This is the relationship Claire has with her boyfriend, but Orlando Bloom’s character Drew says she deserves more. When asked what “more” means, Drew is at a loss for words. He’s not sure what Claire deserves, showing that what one deserves is something they must know for themselves. Others can help you find what that something is but cannot find it for you. It’s similar to how Claire helps Drew find that he is more than his job and failures by sending him on a road trip.

At the beginning of the movie, we learn that Drew is a shoe designer whose latest shoe flopped and cost the company a billion dollars. During a silly attempt at suicide — a knife attached to a handle on a cycling machine — he receives a call that his dad has died. On a red eye home, he meets Claire — a flight attendant on a vacant flight who warms up to Drew but he can’t see how lovely she is. Not because his dad died but because he’s preoccupied with his failure and how the world will know about it after a finger-pointing story is published.

None of that really matters though. What matters is right in front of him — Claire, family, friends — and the creative spirit within him that no failure can take away.

You’re an artist, man. Your job is to break through barriers — not accept blame and bow and say I’ll go away now I’m a loser. You know what’d be really great? Have the courage to fail big and stick around. Make them wonder why you’re still smiling. That’s true greatness to me.

Like I said, sweet and good. And true. And funny. Her next line in the scene made me laugh because I can picture the girl I’m seeing now saying it.

Now would you quit trying to break up with me? You are always trying to break up with me and we’re not even together.”

Elizabethtown is not one of my favorite movies, but I could see it becoming one or how it is someone else’s. It made me laugh and remember the paradoxical simplicity-complexity of love.

The movie is also bold, not afraid to fail. The last ten minutes of the movie documents Drew’s road tip home from Elizabethtown, Kentucky, to Oregon, narrated by Claire and showcasing parts of the midwest that I want to visit, including where MLK was shot and where the best chili is.

I wasn’t quite sure what I was watching, and then it hit me: this filmmaker is following his own lesson in the movie. He’s not afraid to fail. Who the heck appends a road trip to the end of a movie that’s not about a road trip? Cameron Crowe does. Forget the ratings. Do something true to you.