When I just started to explore portrait painting with oil, the challenge was always on the likeness of the face, and I admit that it is still something I care about until today.
Portrait painting is an interesting art. I believe many people will agree with me that it is more challenging compared to still life and landscape.
Without careful observation of the face features, proportion and ratio, you can easily make a person into someone else. When likeness is off, that could be a humiliation for some portrait artists especially when the general public hold up only one perspective in viewing all the portrait paintings.
I understand that likeness is the no. 1 thing that people use to judge between good and bad artists, and that's why many artists strive to fulfill this criteria, regardless of their opinion about what makes a truly amazing portrait painting. 'Likeness' is not unimportant but if we look at the art history, it is not meant to be the only criteria. If it does, many famous artists in history will not enjoy the fame today.
The first portrait I think I have achieved 80% of likeness was the painting of Daniel Craig. By having a pencil sketch before applying the oil paint, I make sure the likeness is achieved so I could just let my brushes follow the lines without too much effort.
However, my mindset changed a little after completing a few portrait paintings. I started to get rid of pencil sketches. It certainly wasn’t because I’m so confident in my observation or painting skills but quite the opposite. With a pencil sketch, I stopped paying attention to constantly judging and amending the painting, which is not a good idea especially for portrait painting. It puts me in the wrong place where I would blindly follow the lines and make more awful mistakes.
Secondly, I find that a good portrait painting contains many different qualities, ‘likeness' was just one of them. If we just pursue 100% likeness at all time, we would fool ourselves into achieving a photo-realistic level that no other art possibilities are allowed. Don't get me wrong, I appreciate the tremendous effort and hard work that god knows how hard it is.
With these understandings, sketching a portrait with oil paint is no longer a fear for me. At the same time, I started my separate pencil sketch to improve drawing skills, and as far as I enjoy the pencil sketch, I know it will benefit my oil portrait painting in terms of sharpening my observation and making my brushstrokes more precise over the time.