The Rapper: Drake
The Singer: Rihanna
Why They Should've Hooked Up: Hold up: Didn't they hook up? Who the hell knows? We're pretty sure they hooked up awhile back. And from the sound of some of Drizzy's lyrics—"One of my baddest women ever, I call her Rihanna/But that's 'cause her name is Rihanna!" on "Made Men"—they've still got some sort of relationship going. Whatever. We think they need to stop toying with our emotions and make things official.