Blind Items from the New Yorker Festival Blog, Part 2

Martin Schneider writes:
More Festival blind items from the New Yorker Festival blog (here’s the first one):

Which television personality got her big break when she won a contest to be a radio host on WRNX, in Holyoke, Massachusetts?

What actor and playwright once played a New Yorker theatre critic in a movie?

Which singer-songwriter once said, “I’m one of those people that will probably look better and better as I get older—until I drop dead of beauty”?

Any guesses?