The President: John F. Kennedy
The Rapper: Jay-Z
What the Hell Would They Talk About? Wifing up the baddest chicks in the game. All of their collective accomplishments aside, the legacies of JFK and Jayhova can best be described by looking at the females that they were tied to: Jacqueline Onassis (and, further, Marilyn Monroe!) and Beyonce Knowles. And plus, we're pretty sure these two playboys would have plenty of stories to swap if they were ever in the same room together.