I just finished this portrait of Clint Eastwood this week. Acrylic on board.
In my quest to be a better portrait illustrator, I drew a sketch of Clint Eastwood from memory - thinking that he had a pretty memorable face. This was a tiny sketch in the corner of my sketchbook.
Later I came back to the idea of simplifying Mr. Eastwood's face and drew a line drawing in Illustrator, but I could not properly get his iconic squint to look right and it occurred to me that his brow sort of made an "X" across his face so I ran with it. I thought it made perfect sense, also because his character in one of my favorite movies, "The Good, The Bad, and The Ugly" is known as "The Man with no Name."
For the painting, I decided a brooding sunset would make a good background because he is older and nearing the end of his career. Also, the movies he's made in the last 15 years or so have been pretty heavy dramas. I scanned in the background I had painted first and layered the vector sketch on top to play with placement and colors. I decided he should be in the lower third of the frame to make the space in the sky more heavy and weighty. I also needed to see what I should do with his shirt. Blue was used in his hair and features to stand out from the orange in the sky immediately next to his face. I liked the blue dot graphic elements on his shirt, but I couldn't justify why I had put them there. There should be a meaning if I chose to be so bold in a pattern. It was just pure decoration. That might not be bad, and you may be able to figure out a meaning for it, but it was a little distracting for me.
I then redrew the face on the background and started filling it in with acrylics. I build it up gradually with a lot of water mixed in to let a little of the background color show through. I decided to make his shirt really dark like he wore in "Gran Torino." It is a lot less distracting from the focus of his "X"-brow and it brings the balance of the painting back right-side up. Keeps it grounded. I wanted to give the edge an olde-fashioned faded look, but the black I used seemed too much.
It made the whole painting too heavy and dramatic- which was sort of what I was going for, but I wondered if I could make it more pleasing to look at. I scanned this in and worked with it in Photoshop - putting layers of duotone red and desaturated color layered behind the portrait. The background now gives proper attention to the face without being too distracting. This will be used for self-promotion and can be seen on my website markamontgomery.com