David Letterman & JAY-Z Open Up About Cheating

After the news came that rapper Jay-Z would appear as a guest on David Letterman’s Netflix venture My Next Guest Needs No Introduction, led fans to think if the two talk about infidelity.

David Letterman & JAY-Z Open Up About Cheating

At the helm of the Late Show back in 2009, Letterman revealed to the audience that someone blackmailed him who knew that he had sex with female staff members. A few days later, he apologized to his mother, wife, and his 14-year-old son Harry, Regina Lasko, for cheating.

Suspicions that “The Story of O.J.” singer has strayed during his marriage to Queen Bey grew after she released Lemonade back in 2016 with tracks seemingly about her hubby’s affair. The raper copped to cheating claims in an interview with The New York Times’ T Magazine which was published in November.

Letterman jokingly said that Jay-Z was his “twin” early in their Next Guest talk, but it isn’t until their conversation near its end that the My Next Guest Needs No Introduction host brings up their overlapping transgression.

The host said without providing specifics of the incident, “I did something that I had no business doing, and I regret it, and since then I have tried to acknowledge that mistake and be a better person.” He continued, “You can only stop behavior that was hurting people and apologize for it and try to continue to be a better person.”

The Mark Twain prize recipient went on to say, “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 for so many people.” He said, “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 would see my son every two weeks, 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 and they would tell me various things to just get me out of the office, but I never talked to a person who had had been in that situation,” the host added. “I’m wondering if this rings a bell with you, the pain of ‘Have I done something now to blow up my family?’ ”

JAY-Z replied: “Yeah.” He said, “For a lot of us we don’t have — especially where I grew up and men in general — we don’t have emotional queues from when we’re young. Our emotional queue is ‘Be a man, stand-up, don’t cry.'”

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