Oregon Storyteller: Bill Oakley

 concepted, directed and photographed by Andy Batt

How do you get better at storytelling?

Two ways, I think. You practice—and you copy. Obviously, the more you do it, the better you’re going to get, especially if you get good feedback or constructive criticism. This is common sense.  But the copying part, THAT’s what you shouldn’t be afraid of. You can learn a great deal by reverse engineering your favorite stories, shows, and films. We copied the entire seventh season of The Simpsons from the third season, on purpose, and it worked great.


What’s the biggest difference between the way you worked as a younger writer and the way you work now? 

I used to insist on writing a script all the way through, in order, perfectly. I wouldn’t move to page 2 until page 1 was completely perfect. I later discovered this was insane. Now I write the fastest possible first draft and take my time nitpicking my way through the next few drafts.


When do your ideas show up? Or maybe where is a better question? 

They invariably show up in the car when I am driving and I have no ability to record them or write them down. I’ve lost a lot of potential Emmys this way.


Do you laugh at your own jokes after you’ve rewritten, polished, adjusted and made them perfect? 

A: Not at the time, I’m too busy second guessing them. But after they’ve aged nicely on my hard drive for a decade or more, then I open them up like a fine wine and have some laughs—usually.

What are the key elements that make a good story? What needs to be there to get you excited?

Years of overseeing storyboards have taught me to think visually and picture how a story or scene will play out on screen. So I have to be able to picture it in my head. I also have to be able to see the comic potential of an idea, which sometimes has to be coaxed out. And I have to be able to see an ending, or at least a path to one. If I can see all three of these things, I’m onboard.


What do you do to get past your creative blocks? 

I walk. Sometimes for miles and miles and sometimes just a far as the kitchen. It always works. Maybe it’s something about resetting your point of view or just getting your blood flowing. Nietzsche, who I’m not normally a big fan of, said “All truly great thoughts are conceived by walking” and it may be his wisest quote.


What’s the most unlikely place that you’ve found inspiration? 

Inside an old caboose at a train museum. I am confident the world will be blown away by my magnum caboose opus.


How do you hold onto an idea that feels like it will slip out of your grasp? 

I don’t. I think an idea slipping from your grasp is your subconscious telling you to change the subject.


What’s uniquely different (or difficult) about comedy writing? 

Comedy writing is the only type of writing where no matter what you do, at least 25% of the audience is going to dislike it. Comedy is very subjective. No matter whether you’re Patton Oswalt or Jay Leno or Dave Barry or Amy Schumer, some large percentage of the audience just won’t be on your wavelength—and trying to please everyone is a guaranteed path to failure or maybe doing stand-up comedy on a cruise ship.


Archie Comics: Innocent or Subversive? 

99% innocent and 1% subversive which is the (secret) formula to its particular genius.


Best Footwear Name: Sneakers, Loafers, or Galoshes 


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  1. says: Kimberly Shumate

    Thanks to Bill Oakley for taking the time to do this interview. From all of us Oregon comedy writers finding the path to funny (in the rain, no less), it can be tough sometimes. Okay, most of the time. However, every bit of wisdom helps immensely.

    Eugene OR