Eustace Tilley is that be-monocled dandy who you associate with the New Yorker. He was on the cover of the first issue in 1925, and now they’re having a contest celebrating his foppish visage. (Not a fan. I think he’s freaky.)
Mark Chadwick’s entry definitively and preemptively gets my vote: He took the algorithmic approach and created a mosaic out of every single cover of the New Yorker.