Republican Tony Ciccone, who lives near Moore's Michigan home, first befriended the FAHRENHEIT 9/11 documentary-maker when Madonna asked him to deliver a case of his wine to mark staunch Democrat Moore's birthday.
The 47-year-old singer says, "Here's the irony of all ironies: he's now really good friends with Michael Moore.
"They live near each other in northern Michigan, where my father has his vineyards, and several things happened.
"It was Michael's birthday, and I wanted to send him a gift. I said, 'Dad, would you drive over a case of your wine? Can you do that for me?'
"He put a whole basket together with pasta and a sausage, and he and my stepmother went bearing gifts."
And Madonna was astonished to receive a phone call from her father expressing his admiration for Moore: "He called me later and casually said, 'Oh yeah, we stayed and had a cup of tea.
"'He's so nice, we really liked him.' I'm like, 'You are kidding me Dad!'"