5. Chelsea Handler Drop
The late-night comedy queen has experience in wooing rappers (hi 50) and we were convinced sparks would fly when Chelsea Handler told the Bawse on her talk show that she "loved big black men!" and said she would upgrade from Fif to Rick. If Peter Rosenberg can get some wax, we're sure there's space for Chels too. She could even sub for the model who does the Maybach stutter for shiggles.