“Rosie, who’s the most fascinating woman in politics?” He was working on ideas for the cover of George’s annual 20 Most Fascinating Women in Politics issue. “Hillary Clinton?” I said. “Yeah, okay. But she already said no to the cover. I’ve got another idea,” he said, looking like the cat that swallowed the canary. “I think we should dress Madonna up as my mother. Wouldn’t that be a riot? We’ll have her in the pillbox hat, sitting on a stack of books.” “That’s hilarious,” I said, turning to get back to my desk, assuming it was just another inside joke. “Great. Will you get your pad? I’m going to write her a note.” “Wait, you’re serious?” “Yeah. You thought I was joking?” I had to give it to the guy. It took balls, and a pretty wicked sense of humor, to entertain such an irreverent idea. He picked Madonna because she was the most controversial figure in pop culture—and they had a friendship. She would acknowledge the concept and be as satiric about it as he was.
