Photographer Lee Jeffries worked as a sports photographer before having a chance encounter one day with a young homeless girl on a London street. After stealthily photographing the girl huddled in her sleeping bag, Jeffries decided to approach and talk with her rather than disappear with the photograph. That day changed his perception about the homeless, and he then decided to make them the subject of his photography. Jeffries makes portraits of homeless people he meets in Europe and in the US, and makes it a point to get to know them before asking to create the portraits. His photographs are gritty, honest, and haunting.
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Photographer and blogger Thomas Hawk has an ongoing project called $2 Portraits in which he gives $2 to people on the street in exchange for a portrait:

[...] I am going to offer $2 to anyone who asks me for money in exchange for their portrait. While I’m taking their portrait I’m going to ask their name and try to learn a little bit about them. I plan on doing this for the rest of my life — assuming that I can afford to.

To make things easier I’m putting $2 in reserve money in a special place in my wallet so that even if I don’t have change I will always have the $2 to hand over.

In part I’m undertaking this project because I realize that I’ve been avoiding people asking me for money. My biggest motivation behind this project however is simply that I think human interaction is a good thing. I’m not doing this to exploit homeless people or show how hard and bad life can be. I’m doing this because I want to celebrate other human beings as human beings and I think that this commercial transaction gives us an opportunity to engage and interact on a more human level… and I also think that I can take a pretty decent portrait.

You can see all of the portraits Hawk has taken so far in his $2 Portraits Flickr set, where he also shares the story behind each photo. If you’d like to start doing the same thing, he also has a Flickr group where people can share their own $2 photographs.

$2 Portraits (via ALTFoto)

While an undergrad at UC Berkeley, I took an advanced photography course in which each student worked on a semester long project with the theme “Downtown Berkeley”. For part of the project, we were told to do a general survey of the area, and I spent hours walking up and down the downtown streets.

On one particular occasion, I wandered past a seemingly tight-knit group of homeless friends, sitting on the side of Shattuck Avenue. Approaching a single stranger is often difficult enough, but I decided to try and befriend the group since I felt like the opportunity was too good to pass up. Turning around, I struck up a conversation with a couple of the guys in the group. I was also carrying some bubble gum that I often offered to people in exchange for portraits (I’ll cover this in a later post), and gave some to the group. After warming up to me, they were more than willing to have their portraits taken for my class.

I discovered that making a stranger comfortable with your presence is extremely important, and determines the kind of portraits you’ll end up with. If you can make someone drop their guard, they’ll be much more animated and natural in front of your camera.

If you spend enough time, build enough of a relationship, and take enough photographs, you’re bound to find a “keeper” afterwards. This ended up being a photograph that helped me win 3rd prize in a pretty prestigious photography contest (the Eisner Prize):

Taking portraits of strangers you meet on the street definitely isn’t as difficult or scary as you might think. You just need to be bold, friendly, and persistent.