Drew Friedman is my absolute favorite caricaturist and probably my favorite living portrait artist. His insane attention to detail and mastery of stippling gives his portraits a surreal-yet-oddly lifelike quality. Mark F. and I can't stop talking about his latest book, Old Jewish Comedians, published by Fantagraphics as part of their excellent BLAB! Storybook series. (Link to Mark's review at Mad Professor.) Friedman takes on all the greats, from Jack Benny, Don Rickles, and the Marx Brothers to Henny Youngman, Bud Abbott, and Sid Caesar. The portraits not only exude the charisma of these funny men but somehow manage to feel "of the time" too. And as Mark said, Friedman is a master at drawing liver spots. Highly recommended.
David Pescovitz is Boing Boing's co-editor/managing partner. He's also a research director at Institute for the Future. On Instagram, he's @pesco.