Length of feud: 5 years A onetime member of his sister's inner circle, Christopher served as everything from Madonna's assistant to the artistic director of her 1993 Girlie Show tour. But that all changed with the release of his 2008 tell-all, Life with My Sister Madonna, in which he dished on her relationship with ex-husband Guy Ritchie, among other things. The siblings stopped speaking, but Christopher told the Huffington Post in December 2012 they've since reconciled. "We are back to being a brother and sister," he said, though admitted, "It's not completely there yet. We are not fully back. It will never be that."