The Rapper: J. Cole
The Singer: Rihanna
Why They Should've Hooked Up: If not Drake, then Cole! We heard aaaaaaall about the alleged sex tape that Penthouse supposedly had in their possession earlier this year. But, it never actually surfaced. That being said, Cole seems a little like Jay-Z's little brother these days (Kanye's all grown up!) and Rih-Rih seems a little like Beyonce's little sister. So, wouldn't Cole and Rih make a cute couple? We sure think so.