The Guy: Drake
Who Is He? If you really need us to explain, please click the "X" on your browser now (But, just for the record, Drizzy and Rih-Rih collaborated on last year's hit single, "What's My Name?")
Why He's Got A Shot: Whether you choose to believe the rumors or not, these two seem to have some sort of romantic past. We're not sure if it didn't work out, they didn't pursue it further, or if it simply didn't exist at all. But what we do know is that Drake and Rihanna are almost the same age (he's 24; she's 23), they're both at the top of their respective genres right now, and they would automatically become the new-age Jay-Z and Beyonce if they ever decided to seriously link up. Otherwise, we'll just have to wait for Drake's inevitable memoir to find out what really happened between them a couple years ago.