Since moving to New York last year, I’ve developed a trick that I use when I pass someone on the street whom I want to discreetly photograph. I’ve tried it three times now, with a 66.66% success rate.
Here’s the scenario: I’ll be walking down the street and glance up and see someone striking and photogenic coming right toward me. I’ll immediately double back at top speed, as though I’ve just realized that I’ve forgotten something important at wherever I’ve just come from. And I’ll whip out my iPhone and launch the camera in the meantime, readying it for action. Then I’ll casually turn back around — as though I hadn’t forgotten anything after all — and head back toward the photogenic person, with my camera set to go at my hip.
Since I can’t see what I’m pointing the camera at, the framing and other results vary. Here’s a guy walking around Midtown in January dressed as Edward Scissorhands:
And here’s one I shot today: Ben Stiller walking around Midtown talking to some woman:
You might be able to see my trick in action for yourself in the next Ben Stiller movie. Because I didn’t realize it at the time, but when I looked across the street after snapping that photo, I discovered the whole thing was captured on film by the movie crew facing us:
The one time I tried this and failed was a few weeks ago, when I passed a blonde woman in the subway who was completely topless, and wearing a black mustache painted on her face. I was totally disoriented by the site, and unable to launch my camera in time. I later found out she’s a performance artist named Holly Van Voast (NSFW).