"I'm not the worst of what I've done," the rapper explains after the host admits to his own "trouble" in the past.
A running joke throughout David Letterman's "My Next Guest Needs No Introduction" interview with Jay-Z was how much the two had in common, but towards the end of the special, they both got candid about some common ground they actually did share: infidelity.
In 2009, the then-"Late Night" host admitted to affairs with multiple female members on the show and claimed he had been the target of a $2 million extortion plot by someone who knew about his indiscretions. He later apologized to his family, including wife Regina Lasko and their son, Harry. The two are still together.
"A few years ago I got myself into some trouble. The situation was my responsibility and my fault and I did something that I had no business doing and I regret it," Letterman said while broaching the subject with his guest on the Netflix special.
"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 continue to be a better person. At least that's all I know what to do," he continued. "I like to think and maybe that's flattery I can't afford, that I'm a better person, not the person that caused to much pain for 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 gonna be in a situation where I was going to see my son every two weeks, my wife would be dating Scott the dentist from New Jersey. But I'd never talked to a person who had been in that situation. And I'm wondering, if this rings a bell with you, the pain of I've done something now to blow up my family."
Last year, Jay admitted he had cheated on Beyonce in the New York Times, something she alluded to in her visual album "Lemonade."
"For a lot of us, we don't have, especially where I grew up and men in general, we don't have emotional cues from when we're young," he responded. "Our emotional cues, be a man, stand up, don't cry."
"I want to have the emotional tools that it takes to keep my family together. And much like you, I have a beautiful wife who's understanding and knew I'm not the worst of what I've done," Jay continued. "We did the hard work of going to therapy and you know, we love each other, right? So we really put in the work. For years, this music I'm making now is the result of things that happened already."
"Like you, I like to believe we're in a better place today. But we're still working and communicating and growing," he went on. "And I'm proud of the father and the husband that I am today because of all the work that was done."
Reflecting on his own past again, Letterman added, "I'm not saying I'm heroic, but I'm as scared as I've ever been in my life, not to discount the pain of others. I can't imagine not coming through it. The end result is still a work in progress, but I now know I'm a different person and my worst fear is not coming to pass."
Those words clearly struck a cord with Jay-Z, who offered Letterman a handshake before they moved onto the next topic.
"My Next Guest Needs No Introduction" is currently streaming on Netflix.