I'm torn, myself, and haven't given it a ton of thought, because it is, after all, a lark. Friedman is amazing at capturing the essence of his subjects, wonderful when he applauds them, devestating when he condemns them. His old comics, often done with his brother, were highlights of the Raw-era. Whenever one of my high school cartoon doodles appears in Mad and there's a Friedman piece I want to throw out my art supplies, he's a master.
Anyway, as for the question: I'm terrible at winnowing things down or making choices even in the most trivial of situations -- friends who have sat waiting while I try to order food at a diner know this all too well. I would most choose a dead entertainer from decades past, perhaps Ernie Kovacs. Or maybe Fred Allen, or Jack Carson, or Oscar Levant. Or a really obscure character actor like Ned Sparks, or Ed Brophy. Maybe Nat Pendleton. Maybe go the other way, Carol Lombarde, or Jean Arthur. Or maybe a horror actor in makeup, a Karloff Frankenstein. Or maybe a cartoonist, Jack Kirby or Ernie Bushmiller...or, hell, I dunno. I should just get more Drew Friedman books, those Jewish Comedians art books are just fantastic and I look through them every time I have them in my hands but haven't had the scratch for 'em yet. I know, poor, poor, nerdboy.
So, anyway, let's talk -- who would you pick? Lay it on me, brothers and sisters.