Definitely the weirdest entry on this list, R&B crooner Brian McKnight was the epitome of nice-guy romanticism and he sang really sensitive lyrics about crying one last time. Then, for some inexplicable reason, in 2012 he decided to release a new song online called “How Your P—y Works,” which was slightly less romantic and sensitive. He, like Jewel, later dismissed the whole thing as a joke. His fans weren’t laughing, either.