Day 1: Chicago
It was a bright July morning, and I was standing on a crowded street in uptown Chicago, across the way from the Green Mill Cocktail Lounge. I’d never been there before, but three years earlier, looking for a distinctive sidewalk to place my character on in a short story, I’d looked the bar up and chosen it. Now, I was across from that spot, with that character standing down the street, waiting for me to call “Action” and summon him to walk into the scene I’d dreamed up. The street was crowded, and we were just a few people with a camera—we weren’t running sound, and most of the crew was elsewhere—so you could easily have missed what was happening, missed the dreamy grin on my face, walked right by the guy having one of the best days of his entire life.
We only had one day of shooting in Chicago, covering two locations: this street scene, and two quick interiors. We'd started the morning with breakfast at the hotel restaurant, where we all signed our contracts and officially bound ourselves to each other for three weeks of come-what-may, and then about half of us grabbed the camera—a RED Epic, which had been shipped to the hotel along with our lenses and other accessories—while the rest of the crew went to pick up the lighting gear and the RV that would be our rolling base of operations.
Out on the street in Chicago adrenaline was high, we were making decisions on the fly, not having been able to do much planning (the joy and the curse of the road movie when the only scouting option is Google Street View), and my main takeaway was: this will be hard work, but this is nowhere near impossible. The years of believing I could never do this, the months of being utterly convinced this was a mistake, it all fell away. We could do this. We WERE doing this. And having fun doing it.
We had a dinner of deep-dish pizza (because we were in Chicago for one night, and what were we supposed to do, NOT eat deep-dish pizza?) and then moved on to our interior location. This was one of those occasions where you really feel lucky to be making a movie in the 21st century. We needed to shoot two short scenes in an apartment, but being my own location scout, I didn’t have much idea how to find an available apartment in Chicago, until a light-bulb went on: AirBnB.
I searched AirBnB for one-bedroom apartments in Chicago until I found one that felt right for the scene, and then reached out to the host, explaining our situation, and asking his permission to use his apartment as a film set. He was amenable to the idea, and we were off to the races.
Shooting in the apartment was smooth, and then we had three scenes under our belt, and we’d made a dent in making a movie. We carried all the equipment down three flights of stairs, sweating and panting even after dark, loaded it into the RV, and drove an hour and a half west to Rockford, just far enough to get a jump on the next day, which was going to be a big one. We checked into the motel, had a crew meeting, and set the time to meet and get started the next morning. The security of a big city was behind us, and we were headed out into the great wide country beyond it, knowing it would be weeks before we saw another town of more than a few thousand people. We weren’t quite a family yet, just a loose assemblage of what make-up artist Hillary would later dub “North American misfits,” but as I looked around at this gang crowded into a small double room, I felt proud, and thrilled, and for the first time in a while, only a little bit scared.