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21. Madonna and Vanilla Ice
While Madonna and Vanilla Ice were never an official item, the two had a fling in 1992. They weren't that serious, but there are a few intimate photos of them in Madonna's photography book, Sex. She's single now, and Ice's wife filed for divorce in 2016, so hey, you never know. They're on our list because we feel like we missed out on an opportunity to see them in action. They could release some killer tunes together, y'all.