It’s unusual to a find a serious, well-executed portrait painting that features a big, wide-open smile. Toothy smiles have become a hallmark of amateur portraits painted as copies of a photographs, without any real effort at originality. There are exceptions, of course.
Some of Frans Hals portraits, for example. And now, this portrait by Jesse Fillingham, a student at the Art Center College of Design in Pasadena, California.
You could also compare this painting to the works of another character artist, but I’ll let Jesse tell you about that, following the image.

“My concept for this one was about technology and kids. I have noticed kids younger and younger getting cell phones, bluetooths, and all sorts of “goodies.” So i thought that it would be fun to do a portrait of a young boy with a bluetooth in his ear, chatting with someone. People have told me that it looks like a twisted Norman Rockwell, which wasn’t purposeful. But definitely like that people are getting that vibe from the painting because Norman Rockwell painted the quintessential American scenes and people. And I feel like this “character” that I painted could exist in an updated Norman Rockwell scene.”
Jesse’s blog entry featuring this portrait can be found here.
And finally, here’s a cropped image which better shows Jesse’s expressive brushwork:






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