10 Things We Learned From Jay-Z’s Interview With David Letterman

David Letterman learns about the rap game, the crack game and everything in between in the latest episode of his new hour-long interview show My Next Guest Needs No Introduction.

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.

1. 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, Tupac of course … Rakim, Big Daddy Kane, Slick Rick.”

Letterman flips the question on its head. “Are there guys who are successful that are not good?” he asks. “Of course,” Jay-Z retorts. “All the time – it’s like everything else.” Letterman presses him to name someone who’s topped charts but can’t rap, at which point Jay-Z diplomatically answers the question with another question. “How ’bout this,” he says. “Who’s on TV in late night, right now, that’s not even remotely funny?” Score: Jay-Z 1, Letterman 0.

2. A trip to London helped Jay-Z narrowly escape being arrested.
“[Crack] was everywhere in the neighborhood,” Jay-Z tells Letterman when he’s asked about growing up in the projects and turning to dealing in order to get by. He was recruited by a local bodega owner to be a dealer, and started making trips to Trenton and selling drugs. “No one survives that,” Jay-Z notes. “You were either going to jail or you were gonna get killed.”

But fate intervened when he headed to London to record with the rapper Jaz-O, also from Brooklyn’s Marcy Projects, who had a deal with EMI records. “During that time, there was a secret indictment, and they swept up and grabbed 30 of my friends, everyone,” Jay-Z remembers. “One of my closest friends, he went to jail for 11 years.”

3. Different rappers succeed for different reasons.
Letterman doesn’t pretend to know the first thing about hip-hop. “What is the flow?” he asks Jay-Z at one point. The rapper is gracious enough to explain a thing of two about good rappers. “You can have a great voice, and you can almost say anything,” Jay-Z notes. “I think Snoop Dogg has a great voice. He can say, ‘One, two, three and to the four,’ and it’s like, ‘Oh my God!’ It just sounds really good. Or you can be someone like Eminem and have amazing cadence. The syncopation [starts rapping “The Way I Am”]: ‘I sit back with with this pack of Zig-Zag’s and this bag. It becomes percussion inside the music.’ There are multiple ways to be really good. And some people just have it all.”

4. The hip-hop star thinks rap has transformed the N-word into “a word of empowerment.”
About a third of the way through the interview – after discussing Jay-Z’s relationship with Kanye West (“He’s like a brother to me … do you get along with your family all of the time?”) – Letterman pivots suddenly and begins to talk circles around the idea of language. “Forgive me for being a dope about this,” he finally says, “but what I’m getting at is the use of the N-word [in hip-hop].”

Jay-Z takes the question in stride. “When someone has used a word to down your entire culture, what hip-hop did is take that word and flip it, use it as a word of empowerment,” he says. “There’s gonna be people that disagree and agree with this, which is fine … Some people are highly offended from another generation because they believe that it’s the last word that people heard before they died. They have a really strong emotional connection to people using the word. But it’s not the word, it’s actually the intent behind the word. People who are inherently racist will just replace it with a different word or a different way to express racism.”

5. Jay-Z wept when his mother admitted she had feelings for another woman.
When 4:44 was released last summer, “Smile” got a lot of attention for revealing that the rapper’s mother, Gloria Carter, is a lesbian. “Imagine having to live your life as someone else and you think you’re protecting your kids,” Jay-Z tells Letterman. “It’s not like now, when everyone’s more accepting of everyone’s lifestyle. There are still people out there living in a different time, but we look at those people as, you’re living in a different time.”

He continues, “For my mother to have to life as someone she wasn’t, hide and protect her kids … for all this time, for her to sit in front of me and tell me, ‘I think I love someone,’ I really cried … I was so happy for her that she was free … I knew [that that she was gay], but this was the first time we had the conversation, the first time I heard her say she loved her partner. She said, ‘I feel like I love somebody.’ She held that little bit back still – she didn’t say, ‘I’m in love’ … And I just started crying.”

6. The murder of Jay-Z’s uncle splintered his family.
Jay-Z’s father left his family when the rapper was “around 10 or 11. “As a kid I had a bunch of anger towards him,” Jay-Z explains. But with time he’s gained a fuller understanding of the circumstances leading to his father’s departure. “His brother had gotten killed in the projects,” Jay-Z explained. “Someone would call him and say, ‘I’ve just seen the guy who killed your brother.’ He would get up from his bed with his children, take his gun and leave the house. At some point, my mother was like, ‘you have a family here.’ But she didn’t have the language she needed to say, ‘we love you, we don’t want to lose you as well.’ So her fear came out like an ultimatum to him … That splintered their relationship. From there he was in deep pain, started using heroin and things like that.”

7. The famous East Coast vs. West Coast rap rivalry of the 1990s was misguided.
“The idea of the rap beef … it really started as a competitive sport, like basketball,” Jay-Z says. “In order for me to get on the mic and rap in front of the crowd, I had to be the best. So you’d say your best rhyme; I’d say mine. It wasn’t a hostile thing. Let’s make each other better. We weren’t even rapping for ourselves in the beginning. We were rapping for the DJ. The whole idea was you were supposed to keep people interested in the DJ … that’s why all the DJs names came first: Eric B. and Rakim, Jazzy Jeff and the Fresh Prince. The MC wasn’t at the forefront.”

He acknowledges the inter-coastal rivalry between East and West, which culminated in the deaths of the Notorious B.I.G. and Tupac, was “really ugly.” “I think now everyone’s learned the lesson of what that can really do; how far that can really go,” he adds. “We lost two amazing people behind that. I think everyone took a step back and said, ‘Whoa: This is not what hip-hop is about.'”

8. Jay-Z’s sixth grade English teacher hooked him on language.
“I just loved her class so much, reading the dictionary” Jay-Z recalls. “My love of words – I just connected with her. She took us to her house on a field trip. She had ice in her refrigerator way back when no one had it. I thought, ‘Oh man. I might be an English teacher.'”

9. Jay-Z thinks President Trump’s actions will help galvanize progressive political activity.
After discussing Jay-Z’s advocacy on behalf of Kalief Browder, who spent over 1,000 days in pre-trail detention at New York City’s Rikers Island before his case was dismissed, Letterman turns bluntly to the President: “I’m beginning to lose confidence in the Trump administration,” he says. “What do you think of that?”

Jay-Z chooses to think optimistically. “I think that what he’s forcing people to do is have a conversation and band together and work together,” the rapper explains. “You can’t address something that’s not revealed. He’s bringing out an ugly side of America that we wanted to believe is gone … We still gotta deal with it. We have to have tough conversations – talk about the N-word, talk about why white men are so privileged in this country.”

He tells Letterman, “It takes people like you, especially all the young people across the country, speaking out and saying, ‘This isn’t right, I don’t represent what he represents, and I’m gonna change that.'” Then the rapper makes a bold prediction: “I think we’ll see record-breaking numbers next election.”

10. Both men believe their marriages are now on a stronger footing after troubled periods caused by their own infidelity.
Letterman’s interview comes to a somewhat awkward conclusion in which the host alludes to his own adultery – without ever referencing it explicitly – and asks Jay-Z, “I’m wondering if this rings a bell with you?” Although the rapper apologized numerous times for straying from his marriage on last year’s 4:44 album, he follows Letterman’s opaque lead, avoiding any direct references to past events in his relationship. He never even names his wife. “For a lot of us – especially where I grew up, and [for] men in general – we don’t have emotional cues,” Jay-Z says. “Our cues are be a man, stand up, don’t cry … I want to be open, I want to have the emotional tools it takes to keep my family together.”

He continues, “I have a beautiful wife who’s understanding and knew that I’m not the worst of what I’ve done. And we did the hard work of going to therapy. We love each other. We put in the work. This music that I’m making now is a result of things that have happened earlier. Like you, I like to believe that we’re in a better place today, but still working, still communicating and growing. I’m proud of the father and the husband I am today because of all of the work that I’ve done.”