I think I've drawn Hillary almost exactly 419 times now, give or take, and I just drew her again for this week's New Yorker. It took me a while to get her face down, partly because she kept rearranging her features and her hair back when she was First Lady, but now she's settled on an appropriate face for public consumption. And I have too; here are few various Hillaries.
The above was for USNews & World Report back about 1995. It's Ebullient Hillary.
This was for the NYer when Hillary was running for the Senate. It's my favorite Hillary so far.
This is a sketch of Hillary I still like, done for no reason except I'd finally figured out how to draw her.
This is the drawing for this week's NYer. It was one of those jobs where the deadline suddenly shrank into a matter of hours as the piece was still being written. So it got a little too tight and careful, but it came out OK in the end, I think. And now seeing Ann Telnaes' masterly rendering of Hillary as something between Judy Jetson and Patty & Selma Bouvier makes me want to try drawing Hillary all over again.