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David Letterman and Jay-Z Frankly Discuss Their Past Affairs

By Dustin Rowles | Celebrity | April 6, 2018 |

By Dustin Rowles | Celebrity | April 6, 2018 |


Growing up, David Letterman was my goddamn hero. No one — not my parents, not my teachers, not my friends — had a more profound effect on my upbringing. I looked up to him; I emulated him; hell, I spoke like him. Conversely, nothing disappointed me as much as finding out that David Letterman had had an affair. It wasn’t like a “celebrity” sleeping around; it was like my goddamn Dad cheating on my Mom. Actually, worse: Because my Dad did cheat on my mom, and vice versa, and I found that less disappointing than learning that Letterman had cheated on his wife. It hit me hard.

All of which is to say: I appreciate how hard that Letterman has worked to not only earn back the trust of his wife and family, but the rest of us, not by dismissing or justifying or making excuses for, but by owning up to that mistake. By being a model in how to confront those mistakes.

In this week’s “My Next Guest Needs No Introduction,” Letterman speaks more frankly than he ever has about it, and he does so with Jay-Z, who obviously had similar problems with infidelity. I’m probably biased here, but I think this is a textbook example of how men should confront those mistakes. It takes place at around the 50-minute mark of this week’s episode, but here’s the transcript:

Letterman: You and I have one other thing in common … a few years ago, I got myself into some trouble. The situation was my responsibility. It was my fault. I did something I had no business doing, and I regret it, and since then I have tried to acknowledge that mistake and be a better person. You can only stop behavior that was hurting people and apologize for it, and try to be a better person.

I like to think, and maybe this is flattery that I can’t afford, that I’m a better person. Not the person that caused so much pain to so many people. But, at the time, the pain that I caused myself was the fear that I had blown up my family. That I was going to be in a situation where I would see my son every two weeks, that my wife would be dating Scott, the dentist from New Jersey. I would go to therapy and I would talk to people about this situation … but I never talked to a person who had been in that situation. And I’m wondering, if this rings a bell for you. The pain of worrying that I blew up my family.

Jay-Z: Of course. For a lot of us, and men in general, we don’t have emotional cues from when we were growing up. Our emotional cues were ‘stand up, be a man, don’t cry’ … I wanna cry. I wanna be open. I wanna have the emotional tools to keep my family together. Much like you, I have a wonderful wife who is understanding and knows that I am not the worst of what I have done. We did the hard work of going to therapy. We love each other. We really put in the work … like you, I like to believe I’m in a better place today but still working, still growing … and I’m proud of the husband and the father that I am today.

Letterman: It’s hard work … it’s as scared as I have ever been in my life. But, I can’t imagine not coming through it. I can’t imagine not having, you know. But I now know I’m a different person, and my worst fear is not coming to pass.

Beyond that, they also had an interesting exchange on the Trump Administration:

Jay-Z: I think that maybe it’s a wonderful thing. I think that he’s forcing people to have a conversation, and for people to band together and work together. You can’t really address something that’s not been revealed. He’s bringing out an ugly side of America that we wanted to believe is gone. But it’s still here. And we still got to deal with it. We have to talk about the n-word. We have to talk about why white men are so privileged in this country.

Letterman: I completely agree. I think, and I’ve said this a thousand times: We don’t need any more evidence … Is he a racist, or not a racist. I’m telling you, if you’re having a debate over whether a guy is a racist or not a racist, chances are that guy is a racist … The humanity that this country has to represent has been refueled by this dumbass, and because I don’t have any answers, I keep thinking that this problem will take care of itself … I think it will take care of itself. Somehow. We can’t continue.

Jay-Z: It takes people like you, and especially young people across the country, to speak out and say this ain’t right. This is not how I feel. I don’t represent what he represents and I’m going to change that. This is going to get more people active than ever. I think we will see record-breaking numbers in the next election. I think we will break every record.

I don’t know what I was expecting when I tuned in to see Letterman have a conversation with Jay-Z, but whatever it was, this far exceeded those expectations.

Check it out on Netflix.

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Dustin is the founder and co-owner of Pajiba. You may email him here, follow him on Twitter, or listen to his weekly TV podcast, Podjiba.