Tonight marks the end of David Letterman's 30-plus-year career as a late-night host, during which he effectively changed the humor and intellectual discourse of the nighttime talk show format. Letterman's time as a broadcaster happened concurrently with the rise of hip-hop, and because of this, their moments of intersection have resulted in memorable television. From the Beastie Boys performing on the streets of New York City to Letterman's interview with Rosie Perez inadvertently coining the "Funkmaster Flex Night" drop, it’s always been interesting to see Dave and hip-hop culture collide, but the most compelling of Dave’s interactions with hip-hop has to be his interesting relationship with Jay Z.

Jay’s first appearance on Letterman dates back to Nov. 10, 1998. With the couch occupied by Luke Perry and Tom Wolfe, we didn’t get any interview time with Jay. He would return five years later to promote his supposed final release, The Black Album, on Nov. 26, 2003. With the only other guest being Mike Myers, it was another example of the levels Jay was reaching in terms of pop culture ubiquity.

Being the multimedia megastar that he is, Jay’s appeared on pretty much every major television talk show program. After all, when you’re friends with the President of the United States, people tend to want to talk to you. But, for some reason, it’s Jay’s Letterman appearances that have always stuck out as the most memorable. Maybe it’s because the always New York-minded Jay sees Letterman’s broadcast career as one of the city’s most consistent representations on television. Maybe it’s the hustler's spirit Jay sees in Dave; someone who also risked it all to create his unique empire and stayed true to himself. Maybe Jay just thinks he’s funny. Whatever the reason is, the Shawn Carter you see next to Letterman is a different Jay than you get in any other interview scenario. Here's a look back at the conversations between Jay and Dave over the years, and the final one that never came to be.

Chaz Kangas is a writer living in New York. Follow him @Chazraps.