When Kendrick Lamar walked onstage for his performance at this year’s Grammy Awards, hands cuffed and clinking as part of a chain gang, saxophone player Terrace Martin stood to his left, blowing doleful notes from inside a jail cell. Lamar won five awards that night, including Best Rap Album for To Pimp a Butterfly, a record that heavily features Martin. The prison imagery gave way to pyrotechnics and ended with Lamar’s frame silhouetted against a map of Africa, with his Compton hometown labeled where the Sahara desert would be. Joined by all African-American dancers in front of a largely white Staples Center crowd, the blazing medley of TPAB’s “The Blacker the Berry” and “Alright” carried a sense of history in the making.

This momentousness was embodied in the music, a heady update of pointillistic astral jazz and hypnotic G-funk. It’s fitting that Martin, who’s producing records for Compton rapper YG and jazz legend Herbie Hancock, later told a reporter the first face he saw from stage that night was the veteran pianist’s. At the 1984 Grammys, Hancock’s keytar-wielding rendition of crossover hit “Rockit” marked another milestone for hip-hop, jazz, and pop culture overall.

From the awards-show stage to fellow TPAB collaborator Kamasi Washington’s 2015 saxophone opus The Epic, jazz and hip-hop are colliding in beautiful ways lately. But jazz and rap have long been close relatives. Jazz, in spirit, is actually something of hip-hop’s ancestor, not only because of rap’s frequent use of direct jazz samples, but also in the shared traditions of African-American free expression, avant-garde experimentation, and even solo parts that build upon each other. First the ensemble jam, then the posse cut.

A master of the nexus between these two crucial art forms was the late Detroit producer J Dilla. Indeed, on “The Introduction,” from his long-lost vocal album The Diary, he raps about listening to Q-Tip, “My pops used to say it reminded him of jazz cats/ See, he told me that this game go in cycles.” If Dilla is correct, the cycle has come full circle again.

The Pitchfork Review reached out to a who’s who of rappers, producers, and jazz musicians working on the borders between the two genres to ask them two questions: What jazz record should every rap lover own? And what rap record should every jazz lover own? Let the cross-pollination of jazz and hip-hop continue.