
That's thanks to his guest, Jay-Z, who good-naturedly fields open-ended questions like "What is the flow?" and "Are there [rappers] who are successful that are not good?" in front of an appreciative crowd that includes director Judd Apatow.
The conversation between the former late-night host and the man once known as H.O.V.A. meanders amiably from the personal (marital troubles, the sexual orientation of the rapper's mother) to the political (the trouble with President Trump, criminal justice reform), often pushed along by the host's amusingly abrupt segues. Here are 10 takeaways from Letterman's interview with Jay-Z.
Jay is into acknowledging his influences – but not into talking shit.
Early in the interview, Letterman likens Jay-Z to Picasso and asks the rapper to select his Matisse. "There's so many great people," Jay-Z replies. "Biggie Smalls of course, Notorious B.I.G... Rakim, Big Daddy Kane, Slick Rick."
Check out the video clip below:

Lost Boyz talk and remember Notorious B.I.G. On “Drink Champs”