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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.
On the Nets and American Gangster
It’s with post-retirement Jay that the Letterman appearances begin to get really interesting. Nov. 7, 2007, saw Jay drop by for both an interview and performance of “Roc Boys” off of American Gangster. Letterman immediately engaged him in a basketball conversation, which quickly gave way to Jay’s largely unseen dry wit. The way Jay laughed with Dave, and Dave’s reaction to the “not so much” line disarmed both men, and their television bromance began. Jay also gave Dave the most straight answer about his retirement we’d ever received, setting the tone for their revealing future conversations together.
On R. Kelly and the Heart of the City Tour
Jay returned the following April with Mary J. Blige to promote their Heart of the City tour. Letterman’s trademark fearlessness to “razz” his guests and Jay’s ability to roll with the punches resulted in the definitive explanation as to the fallout between Jay Z and R. Kelly from the previous year’s Unfinished Business tour. This appearance also gave us an excellent performance of Jay and Mary's collaboration “Can’t Knock the Hustle,” which was almost as great as Jay’s recounting of the moment that made him realize that touring with R. Kelly wouldn’t work.
On Marriage and The Blueprint 3
The next time we saw Jay on Letterman was the day The Blueprint 3 dropped. Probably Jay’s most discussed appearance on the show, fans of just Jay or just Letterman who were unfamiliar with the other led to some online speculation that Jay was “high” and that Letterman was being “a dick.” What this appearance really did was show two guys with similar senses of humor perfectly playing to each others’ strengths. This appearance was also notable as both Jay and Dave had gotten secretly married to their longtime significant others in the previous year, and their discussion on married life was as straight-forward as either had ever been on the topic. This was Jay’s first time as the headlining guest, ahead of Martha Stewart and George Jones.
On Eminem and the Home & Home Tour
The following June, Jay appeared to discuss his upcoming back-to-back concerts with Eminem. Em later joined Jay for a rooftop performance atop the same Ed Sullivan Theater awning that hosted Paul McCartney a few months earlier. It was also great to hear Jay and Dave have a casual conversation about basketball that neither really publicly had with many others. Seeing Jay crack up after Dave’s Boy Scouts/Girl Scouts analogy was an unguarded and genuine moment that the highly polished and produced MC seldom let out.
On Life Before the Fame and Decoded
Jay’s final appearance on Letterman came in November 2010 to promote his book Decoded. In the most extensive of all of Jay’s interviews, Dave and Jay went deep into Jay’s early pre-fame years. While the other interviews were fairly light, funny conversations, this appearance with Letterman had Jay bringing the graphic realities of life in the projects to every living room in middle America. While it was also notable for Jay’s shout-out to Jaz, the rapper who put him on tracks like “Hawaiian Sophie” in his early years, this interview was as candid as Jay’s ever gotten about his origins and his craft.
On the Last Letterman Appearance That Never Was
Sadly, Jay’s scheduled appearance on Letterman in July 2013 to coincide with the release of his Magna Carta Holy Grail album never materialized. Rumors persisted that he was supposed to once again perform atop the marquee at the Ed Sullivan Theater on July 8, but the New York Post speculated the last-minute cancelation was due to possible police concerns over fireworks and terrorism. Jay has not returned since.
With Letterman exiting television tonight, it also means we’ll never get to see the dry-witted, disarmed Jay Z alongside him again. Revisiting each of these moments, from Paul Shaffer and the CBS Orchestra’s arrangement of Jay’s singles to the types of conversations Jay doesn’t typically have with traditional rap media, it’s the end of a really special partnership. While seeing “Dave-Z” surface on a Jigga track is probably the most wishful of wishful thinking, their relationship on television is unlike anything else the hip-hop media has seen, or will likely ever see again.