What Makes Great Street Photography?

A picture says a thousand words, right? It tells a story. But, that story isn’t always the truth. For photographer Jack Simon, the goal is to tell a story that is mysterious, surprising, funny, a little bit ridiculous, and just plain out of the ordinary. Simon spends much of his time walking the streets of San Francisco in search of unposed street photography shots that trick the viewer into seeing something fictional, even a little magical at times. Here’s how he captures these odd photos:

Simon’s images have the unique ability to make the viewer’s brain come up with stories that aren’t really happening. He admits that he’s attracted to images that are humorous, strange, and surreal, and he strives to find scenes that capture the essence of an imagined story.

capturing odd moments photo

“These fragments of fictional stories are drawn from the real world in an odd coupling of my unconscious, my intentions, and chance.”

mystical street photography

In his mission to find these rare moments, Simon enjoys wandering the city streets, not looking for anything in particular, but excited for what he might find. One of his most popular images is this shot of what looks like a man painting a picture of a homeless man passed on on the sidewalk.

painter paints homeless man photo

In actuality, the painter’s subject is the man in maroon. But, as Simon came upon the scene, he found the whole setting bizarre, even after he discovered the passed out man was not the subject. So, he snapped the shot and it is the perfect example of how this kind of street photography can trick the viewer and add an element of mystery to everyday life.

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