Joel Grimes is my portrait hero. He typically lights his subjects with a signature three-light configuration. Most of his images are Photoshop composites, in which he places his "cut-out" subject onto a separate background photo. Some photography purists balk at this level of manipulation, but that's akin to a portrait painter, saying 150 years ago, that photos aren't "real" portraits. The reality is that Photoshop is the modern darkroom--a new (and powerful) tool in image creation. Moreover, Joel doesn't look at himself as solely a photographer, but rather an artist.
Joel might describe his process is somewhat fluid. Sometimes he takes the background photo and then shoot a subject to use with it, and sometimes he reverses things, shooting the subject first and then looking for the "right" background. He tends to shy away from technical tools such as light meters that might override an artistic decision. However he does it, whether it's due to years of experience, artistic training, or natural talent (likely all of the above), he is a master at his craft.
Taking some tips from my hero, on a trip to visit my brother in Florida, I decided I'd look for scenes to photograph to use as backgrounds for future composites. My brother suggested I check out the University of Tampa University campus. I did, and the background in this portrait of Zena was one of my take-aways. Less than a week later, I shot Zena in the studio using a three-light setup, thinking I might create a composite portrait, but with no background in mind. Then, I stumbled onto the combination in this image as I was copying the photos from my trip and the shoot with Zena onto my computer (many of the photos were on the same memory card). Zena's dress and subtle pose went perfectly with the background. Dumb luck, but it remains one of my most favorite portrait composites to this day. The best compliment I've received on it was from my wife, who saw the photo and assumed I had done a photoshoot (with the model on location) in Tampa while visiting my brother :-)
Model: Zena Q
Kristoffer Cox Photography: Artisan Portraits and Conceptual Images