Lessons from a Hollywood Pin-Up
By Elizabeth Cutright

What are you not trying today? What are you too scared to attempt?  What intimidates you?

Have the things that frighten or overwhelm you changed?  Did you once imagine yourself in another profession or leading a different life, one that now seems utterly improbable or impossible?

I guess I’m just wondering if anyone else suspects they are not “living up to their potential.”

When I was younger – fresh out of college – I conjured up a vision of adulthood that included a career as a screenwriter.  Forget the fact that I actually hadn’t necessarily enjoyed my undergraduate screenwriting class; I was in love with the movies and wanted  somehow to participate in their creation.

Then I got cold feet and applied to law school.

It’s not an unusual story – most folks pursuing a JD are there out of fear and a feeling that they should “have something to fall back on.”  In fact, I suspect that less than half of my USD classmates are actually practicing nuts-and-bolts law today.

But as I’ve explained so many times before, though I don’t regret degree, what I actually learned in law school was that I was meant to be a writer.

And it took another 10 years to plant a lasting foothold in the publishing world – a fact I try to remind myself of every time I get frustrated with a persnickety contact or grumpy freelancer.

When I’d “jumped ship in Hong Kong” and wandered the wilds of the Mohave Dessert (that’s a nod to my good, old friend –or old, good friend Steve, who loves to quote Bill Murray’s Caddyshack soliloquy), I tried my hand at a freelance career.  Without much to go on, I scoured the Writers Market and subscribed to a bushel of consumer magazines – including Premier and Movieline, two now-defunct publications who’s lively coverage of the film industry always kept me “in-the-know” and made me feel as if at career in Hollywood was not a totally ridiculous ambition.

During that time, a bit of a fairytale aura began surrounding the film Good Will Hunting.  Here was a story that hit the “American Dream” sweet-spot – two young, handsome actors decide to write their own script after becoming frustrated at the lack of acting opportunities available to them.  A couple of strokes of luck – including the phenomenal fortune of getting that script in front of Harvey Weinstein – and suddenly their film was in production, with each of them playing a role they’d tailor made for themselves.

The film was, by all accounts, an unmitigated success: nominated for Academy Awards for Best Film, Best Director, Best Screenplay, Best Actor and Best Supporting Actor and grossing more than $225,900,000 worldwide.  Both those young writer-actors (Ben Affleck and Matt Damon in case you managed to forget) were catapulted to stardom, Robin Williams won his first Oscar for acting for his portrayal of struggling but empathetic psychologist, and Affleck and Damon were nominated – and ultimately won – the Academy Award for best screenplay.

Quite a sweetheart tale, and a hard one to resist for most entertainment journalists…  So while I was stuck out in the desert with temperamental internet access and nary a clue about crafting a creative career, Damon and Affleck became totems – symbols of what can happen if you decide to craft your own destiny.  Essentially they wrote themselves into their careers.

But it takes a lot of faith to pursue the road well travelled but rarely mastered.  Plenty of people try their hands at acting or writing or singing or any other entertainment based employment.  Few make it to the top.

But I bet most never regret having tried.

What have you given up on?  What have you failed to try?

Tonight I get the chance to finally meet – from afar at least – one member of that award-winning screenwriting team.  Ben Affleck is set to receive the Modern Master Award at the Santa Barbara International Film Festival this evening, and I’ll be sitting there, cheering him on (if for nothing else, his remarkable feat: navigating the deadly Bennifer debacle and transforming himself into a well respected film director) and taking notes.

I’m hoping he’ll discuss those early years.  I want to hear what it took to write that script and where that sense of accomplishment finally emerged – was it when they typed “The End” on the last page?  Was it when Harvey gave it the green-light?  Did it happen when the film premiered and began winning awards?  Was it the Oscar nomination, or did winning the Academy Award finally make that indelible mark.

Check back soon for my report on the event.

And in the meantime, in case you still need some motivation…one of my favorite scenes from Good Will Hunting: the moment Affleck’s character Chucky tells Will he must follow through on his potential; hiding out in a Boston stockyard is no longer an option.

Related articles

• Good Will Hunting: An Oral History – Fifteen years after the release of the movie that made them stars, Matt Damon and Ben Affleck – along with the rest of the cast and crew – reflect in their own words on how a long-shot film by two unknowns became one of Ho (bostonmagazine.com)
• Matt Damon: Ben Affleck Turned To Directing Because He Was In ‘Actor Jail’ (huffingtonpost.com)
• Goodwill Hunting (epicureandealmaker.blogspot.com)