CheckMating – 15 years later.

For some reason, a lot of people have been asking me lately about my former life as a filmmaker, so I thought I’d post one of my most successful films, CheckMating on YouTube for all to see.

About 15 years ago, I was riding a bus to work in Seattle, where I was living, and a little nugget of an idea came to me:

A woman who tests her dates by playing chess with them. CheckMating.

So simple. At the time, I was a filmmaker working at a motion picture laboratory. I had recently completed a half-hour 16mm nugget called Greenwich Meridian, which was a pretty standard first film: artsy, opaque and pretty much unwatchable. I was ready for a new challenge – to make a film people actually wanted to see.

CheckMating had a number of things going for it. It was short –  half-hour films were hard to program at film festivals because they were too long to open for a feature film and too short to stand on their own. I pictured CheckMating with no words, just images and music, which would make it perfect for the international film festival circuit. And I was pretty sure that I could shoot it on 35mm film, and have it look amazing on the big screen.


So I budgeted the film out at $12,000 and started looking for deals. Although I wrote, produced, directed and edited CheckMating, my biggest skill as a filmmaker was always as a producer. I found a free camera, free short ends of 35mm stock, a free editing location. My peers at the motion picture lab where I worked were willing to slide my footage through as “test” footage and not charge me. I ended up bringing in the film for 15% of my budget, a mere $1,800 all in.

It was a one day shoot at a friend’s house. The actors were awesome, especially Amy DeBourget who carried the film. The crew was a dream. The musicians on the soundtrack were brilliant.

It was a charmed little production. I was super-pleased with the final product and I started entering it into film festivals. I had entered my previous film into 18 film festivals and gotten rejections from all of them. With CheckMating, I was accepted into the 19th festival I applied to. Perseverance paid off. I found out after coming back to work from my honeymoon in July of 1996 that I got into the Boston Film Festival. More acceptances poured in, and by the time the film was done on the circuit, it had played something like 60 festivals, events and showcases, and picked up a few awards along the way.

And this little film inadvertently led me to where I am today. As a filmmaker I was an early adopter of screening my films online. I just wanted people to see the film, and wasn’t snobbish about how that happened. While many filmmakers were pontificating about the beauty of film (and not video or digital), I wanted to open source the damn thing (although I’m not sure I knew what open source was at the time).

I got a distribution deal with a little start-up in Seattle called AtomFilms. They were a great group and I was their seventh acquisition. They did extremely well as a company, defining what online film distribution could look like, and sold my film to airlines to show in-flight, to websites seeking quality content and to TV stations around the world (international sales validated my choice to make the film silent). I was written up in the NY Times and the San Francisco Chronicle as a filmmaker willing to try new things. The film was a success. CheckMating even made money, given the minuscule budget I was working with.

That early embracing of the web, as well as an eventual job at AtomFilms as a web producer in charge of their online community of 1.8 million fans steered me onto a new path of doing web stuff instead of film stuff.

And then more recently AtomFilms was bought out by MTV and the rights to CheckMating reverted back to me. And so I have put it up on YouTube where it can be seen once again.

One of the biggest lessons of filmmaking that I draw on everyday is the ability to work with people as they are. Directing actors was perhaps my favourite part of making films. The collaboration, the creativity, the connections. Every actor is different and the key to being a successful director is knowing how to connect and communicate with each actor individually to elicit their best performance. Some actors like line-readings, some like deep philosophical discussions about the character’s motivations, some meditate, some pick fights to work themselves up. Working with each actor in the way most suitable for them is a skill I still draw on daily as a team-member, as a manager and as a contributor to an organization I believe in.

I hope you enjoy this glimpse of my filmmaking side. It’s good to have this film out there again…

16 thoughts on “CheckMating – 15 years later.

  1. Bob Littlejohn

    William, Man #1 in CheckMating was my college roommate, then known as Eric Zook though he took the name Adrian Amadeus later. We roomed together in 1977 at the University of Oregon. Eric died in 2004, from cancer, I think:

    I didn’t know him for very long but I knew him well. He an amazing person, both smarter and more athletic than almost anyone else I have ever met while just a great human being with a fantastic sense of humor and of adventure. We did a Christmas Eve hike up beyond Multnomah Falls, the ice from a recent rain on every tree branch and the trail sparkling with ice crystals in rare brilliant sunshine, nobody else around. He was so excited about the natural beauty.

    One night after a long round of beer Risk we got into a wee bit o trouble on the campus. Eric, who was on the U of O soccer team, ended up getting chased by a campus rent-a-cop throughout downtown Eugene. Turns out the cop was on the track team so they were both great runners; the chase went on for miles. Steve Prefontaine was one of Eric’s friends, incidentally, and he appeared in a bit part in the film “Pre.” In the end Eric dove into a dumpster behind a restaurant to lose the guy and later threw pebbles at our dorm window to ask me to let him in because he had lost his key. I had meanwhile taken a trip to the dispensary with an officer of the Eugene PD who thought my little head injury was sufficient punishment. We had climbed the main administration building on campus earlier in the night and I hit my head on the fire escape ladder. That building was made famous by the scene with the horse in the dean’s office in Animal House which was filmed while we were there.

    As was common back in those days without social media we lost touch after I left school to join the Navy. I was shocked many years later when I tried to find him online and found that he had died, an amazing person who left the earth too soon.

    I would appreciate any memories you might have of Eric from making your remarkable film. I have watched it several times and it’s always a treat. Thank you for this post, and your work.

    • Hi Bob, thank you so much for your comment.

      I met Adrian through the main actress in the film, Amy DeBourget. She thought he would be perfect and as soon as I met him, I agreed.

      Adrian was warm and smart and very very likable. I didn’t know him well, but I will always remember him so fondly.

      I was sorry to hear he died, someone told me after it happened. So unfortunate and so so young.

      It means a lot to me you took the time to write your comment and share your memories. That was wonderful. Thanks Bob.

  2. Oops, sorry. I don’t know how well you know me :-D, but, yes, you’ve met me. I’m Anna from MI team.

  3. @apricat Yes, from a purist point of view there are definitely some errors in the game, but the intention was to focus on the relationships and the woman’s imperfect search for a mate.

    Please share it, absolutely.

    My son is six. He shows no interest in chess yet, too many rules, but we’ll see.

    Out of curiousity, who is this, do I know you?

  4. Hey, yes, my hubby made the same comment about the board turned, naming debuts and commenting moves… 🙂
    He likes it and wants to share it on chesspro forum if you don’t mind 🙂
    How old is your son?

  5. Hi @apicat . Thanks. I used to play, and people have pointed out that the board is actually turned 90 degrees off from regulation play. So obviously I didn’t do quite enough research. I will start teaching my son chess in another year or two…

  6. Hey, this is pretty cool movie, I like the idea. Do you play chess yourself?

  7. awesome! i love the second guy.

    so filmmakeing is the last and next career?

    Nice work amigo !

  8. Lars Johansson

    Cool, William. That was fun to read and view. Much better than playing chess with the grim reaper!

    Movies have more in common with websites than some may think.

  9. This is really great William. Thanks for sharing.

  10. As a critic I think it needed more Sean Connery crashing his Hummer into a streetcar while being chased by Nicolas Cage on a motorcyle… oh, never mind.

    Any film that’s clever, funny, was made for $1800 and includes “Strangers In the Night” in the soundtrack is worth viewing. I showed it to my wife: she still doesn’t want to play chess with me.

  11. You guys are too kind.

    It’s funny, in Seattle people don’t know I’m in “banking” and up here people don’t know I made “films”.

  12. Rob Cottingham

    I’m so happy you’ve decided to share this with the world – and that I finally got to see it! Thanks for bringing a smile to my face on this grey Thursday, you insanely multitalented man.

  13. Bil Repenning

    Fun to see this on the web! You are still my favorite filmmaker!

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