Jay-Z speedruns Letterman into understanding why he won't slander rappers

A journalist told Letterman that JAY-Z is the Pablo Picasso of popular culture music, so Dave asked Hov who would be his Matisse (Picasso’s only rival/competition). He named Biggie 1st. Then, Dave tried to get Jay to name a successful rapper who can’t rap & Hov instantly flipped it on him to make him understand why he wouldn’t give him an answer.