This illustration was created in collaboration with Cody Small at Caava Design, for an upcoming beverage label. Cody and I had been admiring each other's work, so we jumped at the opportunty to work together.  Not only is Cody an excellent designer, I discovered that he's one heck of a great guy!
Our working process was like Barbra Streisand's voice...smooth as butter.
The client wanted an older gaucho with a knife. In the sketch phase, I played with his stance and expression to convey a range of messages from charming, to suspicious to outright dangerous. This guy has a playful look in his eyes, but is ready to duel, with a blanket wrapped around his front arm for defense.
This guy may be talking or chuckling, but he also has his hand on his knife. His head was dropped down to convey the posture of an older gentleman. I did some research on clothing and landscape which informed my decisions. I also started to think about light and shadow.
Another expression and a smaller knife.
After a couple stages of pencil roughs, we were zeroing in on his expression and stance. The knife has gotten much larger and he is sliding it out of the sheath.  His expression is purposely tough to that a smirk?
This is a light and shadow study.  It's also an opportunity to think about how to make him pop off the background.
After this, we decided to lighten the shadows, especially on his face.
Here he is chest up in front of fields, rendered in the woodcut style. 
I created him first, and then used lights and darks in the background to create contrast. 
We wanted the gaucho to stand out.
At this stage, I chose to give his face, neck and arms a rough, weathered look.
Here he is after some final tweaks. His face is lightened, ears shortened and features simplified for a quicker read.
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