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The Best, Worst, and Funniest Moments From Jay-Z’s Interview With David Letterman

For the latest episode of his Netflix show My Next Guest Needs No Introduction, David Letterman spoke with Jay-Z about the rapper’s upbringing, his past as a drug dealer, rap music, race and, yes, infidelity. My Next Guest is often a chore to watch–it’s not that the topics aren’t interesting but that the conversation is mostly surface-level. It’s one part Inside The Actors Studio and one part post-retirement Dave having a casual chat with friends in front of a live audience. This interview with Jay is much of the same thing. The conversation veers too often into flattery, but just when you think it’s going nowhere, you’ll get some nuggets that are actually fascinating.

Below is compiled the good–and bad–moments from the interview:

Best: Jay-Z talks about finding compassion for his father who left him at 11.

“I thought he just left. As a kid, I had a bunch of anger towards him,” Jay tells Dave when asked of the circumstances of his father leaving.

“But, as I grew up, I realize that… the things that he went through in life were very difficult. His brother got killed in the projects, and someone would call him and say, ‘I just saw the guy who killed your brother,’ and he would get up from his bed–with his children–and he’d take his gun and he’d leave the house. And at some point, my mother was like, ‘man, you have a family here.’ But she didn’t have the language that she needed to speak to him like ‘we love you, we don’t wanna lose you as well.’ She didn’t have that language, so her fear came out almost like an ultimatum to him.”

It’s an expression of genuine clarity about the feelings and experience of a man he’d resented for a long time. The kind of insight that feels right out of a therapy session (he talks about going to therapy later in the episode). Jay explains how his father’s grief over his brother ended up consuming his father and causing a rift in the family, which eventually lead to his father’s heroin abuse after he left the family. It wouldn’t be unfair if Jay held onto his own resentment but his explanation of letting it go is actually touching.

Worst: Dave and Jay talk about “the N-word.”

I believe there is a rule that no discussion with a rapper can go on for too long without discussing the politics of using “the N-word.” Dave stutters and stammers about the best method for discussing the word that he hears “with great frequency” but never really finds a footing or direction for what he wants to know; leading to the same boilerplate response of “we took a word used against us and flipped it” from Jay. He acknowledges that people feel uncomfortable and disagree with its use but the conversation is extremely shallow and awkward.

Funniest: Dave and Jay talk about crack.

Letterman, in talking about Jay-Z’s coming of age, has an unintentionally hilarious conversation about Jay’s life as a drug dealer. First, the conversation starts with Dave wondering what the two men have in common: “When I was your age, I had a paper route” to which Jay responds “I had a paper route, too.” Dave then asks him about how he started selling crack to which Jay then responds, “That was my paper route.” It’s a hilarious moment both for Jay’s comic timing and because it’s wonderfully awkward. Dave is wildly oblivious about drug dealing and, crack as a drug, and it’s genuinely amusing—especially when he finds out how much money Jay was making in a week.

Best: Jay talks about his daughter Blue and his mother’s coming out.

This has been written about already in the lead up to this episode but the moments of Jay talking about his daughter Blue Ivy openly discussing her feelings with him and his mother coming out of the closet are sweet to watch.

Worst: The Rick Rubin prerecorded segment

Honestly, this was just boring. There are enough docs on making music that you can watch instead.

Funniest: Dave is confused that rappers lie on their records

Dave: “Hip-Hop is all biographical. Am I right about that?”

Jay: “Uh…. no. It pretends to be. A lot of guys are just telling stories”

Dave: “Really?? Even in the beginning when kids are just starting out?’

Jay: “Yeah they lyin’. 9 times out of 10.”

Dave basically turns into the cosmic brain meme at this discovery before becoming amused by it.

Good: Dave and Jay finally talk about their infidelities

The moment that had to happen finally happened by the end. Letterman went through a very public scandal involving his infidelity back in 2009 while Jay-Z’s own infidelity has been referenced many times over by both he and Beyoncé, and by the end of the episode the two men finally have an intimate conversation about trying to be “better men.” While Dave won’t come out and talk about infidelity, he alludes to it by discussing the fear that he had blown up his family and how that fear propelled him to be better and Jay shares his own thoughts about the long journey of being a better man and husband. It’s a wonderful moment between two men just sharing feelings about their fears and wanting to be better. A perfect end to the episode.


Dave: “I’m dying to know somebody who can’t really rap.”


The Best, Worst, and Funniest Moments From Jay-Z's Interview With David Letterman