In preview clips released online, Em is seen participating in Letterman's famous "Top 10" segment and Jay sits down on the couch to chat with Letterman.
Letterman and the Brooklyn MC discussed Cleveland Cavaliers star (and Jay-Z pal) LeBron James' impending free agency and the arrival of Mikhail Prokhorov, the New Jersey Nets' new Russian billionaire majority owner.
"The tall guy," Hov joked, referring to Prokhorov.
"You're a guy," Letterman then told the rapper. "I'm a guy. Now, if LeBron James wants to be a guy, he will stay where he is and not cut the heart out of that city by leaving Cleveland. You wouldn't do that, would you? Cleveland is in desperate decline. And one of the glimmering hopes they have —"
"How's your ratings in Cleveland?," Jay interrupted to laughs.
Jay, who holds a minority stake in the Nets, admitted if he found himself in a similar situation, he could concede to Letterman's point.
Only three of Eminem's Top 10 items about advice for kids had been previewed at press time, including jokes about "Toy Story 3," illegal downloading, and a dig at BP in the wake of the Gulf leak.
"Don't get mixed up with drugs, gangs or oil executives," the Detroit MC deadpanned.
The two rappers taped their appearance earlier in the week in New York. Initially, they requested to perform on top of the famed Ed Sullivan Theater marquee, but officials for New York Mayor Michael Bloomberg declined to grant a permit.
The pair were able to skirt the issue, however, by taking the show to the rooftop of the building and away from the streets where officials had concerns over public safety.
Eminem and Jay-Z's joint appearance was a part of promotion for their stadium concert series this September in New York and Detroit; two additional shows were announced on Thursday.
What do you think of Jay-Z and Eminem's "Letterman" appearances? Are you excited for the Home and Home Tour? Sound off in the comments below!