15. Drake and Kat Dennings
It’s an odd pairing indeed, but on an episode of Ellen, the singer and renowned lothario said he once went on a date with the 2 Broke Girls star Kat Dennings. It doesn’t appear to have turned into more than one dinner out, but oh to have been a fly on the wall…
14. Madonna and Vanilla Ice
Remember Vanilla Ice, the “white rapper” of the ’90s? No? Well Madonna likely does. She dated the one-hit wonder for about eight months back in 1991. Their bizarre coupling was actually immortalized in Madonna’s racy Sex book, which came out about the same time.