Jay-Z & David Letterman frankly discuss past infidelities on Netflix talk show

David Letterman's conceit for his new Netflix show, to find common ground with his guests, yielded some dramatic material in his latest episode, which saw the comedian and JAY-Z discussing infidelity in their marriages.

At the end of the latest episode of My Next Guest Needs No Introduction, which released on Netflix on Friday morning (Aug. 6), Letterman addressed cheating on his wife and asked if his own experience "[rang] a bell" with the rapper and businessman.

"A few years ago, I got myself into some trouble, and the situation was my responsibility and my fault. 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," Letterman said, never saying the words "cheating" or "infidelity." "At the time the pain that I caused myself was the fear that I had blown up my family … I never talked to a person who had been in that situation. And I'm wondering if this rings a bell with you."

Jay-Z, whose real name is Shawn Carter, responded, "Yeah, of course. 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. Our emotional cues are 'Be a man, stand up, don't cry!'" The rapper went on to say that his 2002 single "Song Cry" attempted to address that he wished he had the "emotional tools" to keep his family together.

"Much like you I have a beautiful wife who was understanding and who knew that I'm not the worst of what I'm done and who did the hard work of going to therapy and really, we love each other. We really put in the work," Jay-Z said, referencing his wife Beyonce. "For years, this music that I'm making now is a result of things that happened already. Like you, I like to believe that we're in a better place today but still working and communicating and growing. I'm proud of the father and the husband that I am today because of all the work that was done."

The late-night host also said that he's changed since he put in work on his marriage: "I now know I'm a different person and my worst fear is not coming to pass." Jay-Z then stood up and shook his hand.

Letterman famously admitted to having affairs with coworkers and cheating on wife Regina Lasko on a 2009 episode of The Late Show, after a blackmailer attempted to extort him for $2 million to withhold the information. Jay-Z has spoken openly about past infidelity against wife Beyoncé since she released her 2016 album Lemonade, which dealt explicitly her husband's relationship with a woman she gave the alias "Becky with the good hair." Jay-Z, in turn, addressed his infidelity in his 2017 album 4:44.

The frank conversation capped an episode that also touched on Jay-Z's opinions on music, his beef with Kanye West and feelings on Trump and current political climate.

Jay-Z, who previously slammed Trump for his immigration comments on The Van Jones Show in January, said that he thought the Trump administration actually was "a great thing." In explanation, the rapper said, "I think what he's forcing people to do is have a conversation and for people to band together and work together. You can't really address something that's not revealed. He's bringing out an ugly side of America that we wanted to believe was gone. And it's still here and we've got to deal with it." He added that he thought that the current administration will bring more young people out to the polls, and that he believed the 2020 presidential election would break voting records.

Letterman and Jay-Z discussed the rapper's continued advocacy for fellow performer Meek Mill, who is engaged in a protracted legal conflict with a Philadelphia judge over his sentencing for breaking parole. In November, Jay-Z wrote a New York Times op-ed in Mills' defense. They also touched on the "99 Problems" performer's HBO documentary series Time: The Kalief Browder Story, about a 16-year-old who was accused of theft and held at Rikers Island for three years without a trial, with time in solitary confinement. "He's not this outlier that everyone would like you to believe," Jay-Z said.

The episode also spent a significant time on Jay-Z's opinions on music, with field segments to the Malibu, Ca.- based Shangri La studio owned by music producer Rick Rubin, where Jay-Z, Kanye West, the Beastie Boys, LL Cool J and Johnny Cash all recorded. Of Kanye West, with whom Jay-Z reportedly has a difficult relationship, the rapper explained, "That's my brother. We're beyond friends. Really, like literally, my little brother is Kanye, and like your little brother, things happen sometimes."

West infamously called out Jay-Z during a long rant at a Sacramento, Calif. concert in 2016 before The College Dropout performer was admitted to a hospital for a psychological breakdown. West also cut ties with Jay-Z's streaming platform, Tidal, last year.

Seemingly for comedic effect, Letterman asked Jay-Z to explain rap conventions to him several times. When he asked if rap songs were all biographical, the rapper laughed, saying rap "pretends to be" from personal experience. Of his use of the "n-word" in songs, he said, "Someone has used a word to down your entire culture and tradition. And what hip-hop did was take that word and flip it and use it as a word of empowerment." And when asked about his definition of excellence in music, he complimented Snoop Dogg's voice and Eminem's cadence, saying that there are multiple ways to be great in the music world.

In a scene that was widely shared before the episode aired, Jay-Z also discussed his mother Gloria Carter's sexuality: While he was recording 4:44, his mother came out to him and later became the subject and co-writer of his song on the album, "Smile." He said that he knew his mother was gay before she told him, and that when she did, "I cried because I was so happy for her that she was free."

Jay-Z's latest tour with Beyonce, On the Run II, will run June 6 through Oct. 2.