I’ve always regarded Jack Nicholson as an easy face to caricature.  But that’s because he’s mostly been caricatured as the Joker, or as a crazy-haired man in sunglasses.  This one turned out to be surprisingly difficult.  I wanted to capture that very specific dull-eyed stare combined with the sinister grin.  It was more trouble than just simply drawing the full-on “here’s Johnny!” face.

In warm ups for this caricature, I tried different sizes of grin, noticing that his mouth actually changed shape a lot.  You think of Jack Nicholson as having one crazy smile, but packs a whole arsenal of unsettling expressions.  What I went with here was a modified version of a grin that shows all the upper teeth, but only the middle few lowers.  It’s bigger for emphasis.

One of Jack’s eyes is usually open just a little wider than the other.  It’s not just Jack, actually, that’s common in most people.  But I wanted to emphasize that for the sake of making him look crazier, so I pointed the eyes in different directions as well.

Plan A was to find a movie still from As Good As It Gets and draw Nicholson’s grumpy writer character, Melvin Udall.  That movie must have been written just for Jack… he’s misogynistic, antagonistic, self-unaware, and an all-around fun bad guy overdue for redemption.  But he doesn’t have facial hair in that movie, and his hair is neat and tidy and short, and, I don’t know, I wanted and older, even crazier Jack.  Anger Management isn’t nearly as good of a movie, but Nicholson practically caricatures himself as Dr. Buddy Rydell, so I get to draw a caricature of Jack Nicholson playing a caricature of himself.

If you’ve never seen As Good As It Gets, check this out: