Z, whose real name is Shawn Carter, was accused in a lawsuit Sunday of raping a teenage girl after an awards show more than two decades ago along with Sean “Diddy” Combs, the hip-hop mogul facing federal sex trafficking charges and a wave of lawsuits alleging sexual assault.

Jay-Z denied the “heinous” allegations, calling the lawsuit a “blackmail attempt.” Here’s a look back at Diddy and Jay-Z’s decades-long friendship. The pair collaborated on each other’s 1997 albums following the death of their mutual friend Notorious B.