David Letterman's Jay-Z interview gets really, really awkward

Jay-Z on ‘My Next Guest Needs No Introduction with David Letterman.’ (Photo: <span>Joe Pugliese/Netflix</span>)
Jay-Z on ‘My Next Guest Needs No Introduction with David Letterman.’ (Photo: Joe Pugliese/Netflix)

The latest installment of David Letterman’s monthly Netflix show is an interview with Jay-Z. It got some attention even before it began streaming on Friday for snippets Netflix released in which Jay-Z talks about infidelity in his marriage to Beyoncé, and about conversations he had with his mother when she came out as gay. When Letterman brings up Donald Trump and volunteers that he thinks Trump is a racist, the rapper says he thinks Trump’s presidency is “a great thing,” because “he’s bringing out the ugly side of America that we wanted to believe was gone” and now we have to “have that conversation and deal with it.”

But this edition of My Next Guest Needs No Introduction with David Letterman is perhaps most notable for how awkward it is. It is well known that Letterman is a big music fan — some of anyone’s fondest memories of his old late-night talk show would include his segments with Warren Zevon, for instance. But when it comes to hip-hop, Dave is out of his depth in a way that is sometimes squirmily uncomfortable. Here’s a sample music question he asks Jay-Z: “By the way, the East Coast/West Coast thing — that’s over?” Here’s another: “Forgive me for being a dope about this. … What I’m getting at is the use of the N word.” If you notice that these aren’t actually questions but more like graceless ways to bring up subjects Letterman is ignorant about and doesn’t know how to frame, then you begin to see how awkward this interview becomes.

Hemming and hawing, dithering and fumfering, Dave admits, in a verbally contorted way, that he’s never paid much attention to hip-hop, which leads to some of his questions and observations sounding inadvertently condescending: “The stuff, it’s very sophisticated,” he says of hip-hop, with more than a little surprise in his voice. “You play with your lyrics,” he observes about Jay-Z’s work. “It’s very complex stuff.” It’s as though he’s praising a child. Jay-Z is gracious and tolerant, while also giving Letterman a sharp glance here and there. When Dave says, “Hip-hop is autobiographical, am I right?” Jay-Z responds, “Uh, no. It pretends to be.” “Really?” says Dave, rather shocked. “Even in the beginning?” — meaning, even when rappers are just starting out. “Yes,” says Jay-Z. “It’s kids lying. Sorry.” He frowns at Letterman as if to say, “Do you really not credit me with imagination?”

Every edition of My Next Guest Needs No Introduction breaks up the interview with taped segments in which Letterman goes on-location somewhere that illustrates some point being made in the conversation. Here, Dave goes to Shangri-La Studios in Malibu, Calif., to talk to producer Rick Rubin, who has collaborated with Jay-Z in the past. Jay-Z is not present for this visit, and these segments end up ignoring his work almost entirely, instead fixating on a woman Rubin is now producing: up-and-coming singer Madison Ryann Ward. Where My Next Guest plays only a few seconds of Jay-Z’s music, the hour makes room for two entire songs by Ward. It’s impossible to avoid the notion that Letterman is far more comfortable showcasing the work of this white woman’s singer-songwriter folk-rock than Jay-Z’s music.

Perhaps I need to say here that I admire Letterman enormously and believe he is the single greatest late-night talk-show host in the history of that TV genre. One reason for that is that Letterman always had a sure sense of who he should interview and how to go about it. That assurance is missing here. Too often, his questions aren’t questions at all but words he blurts because he’s not quite sure how to ask them: “My goodness, your mother is a lesbian” is how he brings up Jay-Z’s mother. Jay-Z is polite enough to rescue Letterman from his discomfort and talk about his mom. Letterman broaches Jay-Z’s infidelity by talking first about his own, but in such a stilted, oblique way — he never actually says the words “infidelity” or “cheating” — that if you didn’t know Dave’s (or Jay-Z’s) past, you’d have no idea what he was talking about. Again, Jay-Z comes to his rescue, courteously.

There’s funny stuff here and there. One unexpected running joke in the hour involves Judd Apatow in a way I won’t spoil. Jay-Z also insults Jimmy Fallon without ever mentioning the Tonight Show host’s name. And I really enjoyed the way Jay-Z takes such pleasure in making Dave squirm when he brings up Letterman’s wealth. Squirming discomfort — some of it pleasurable, much of it not — proves to be the subtext that runs throughout this entire hour.

My Next Guest Needs No Introduction with David Letterman: Jay Z is streaming now on Netflix.

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