Believe it or not, the Notorious B.I.G. and The Roots had beef back in the days. Unfortunately, the Philadelphia group couldn't patch things up with the late rapper before his untimely death in March 1997. Drummer Questlove detailed his Biggie story during an episode of the Juan Epstein podcast.
Ever since Dave Chappelle released the doc 'Block Party' in 2005, he's been heavily associated with hip-hop, so it makes total sense that he would recruit some of the game's biggest rappers and singers to join him onstage once more.