Chappelle knew Sean's pops.
Big Sean was able to grab Dave Chappelle for his latest album Detroit 2 on a skit called, “Story by Dave Chappelle.” Chappelle isn't one to just hop on rap albums out of nowhere, so it was interesting to see his name on the tracklist. According to Big Sean, in an interview on Apple Music 1, Chappelle was a fan of his father before he even knew the rapper. “He was like, ‘I love your dad, man. I love your dad,'" Sean stated. “And I was like, ‘What?’ He was like, ‘Bro, I love your dad.' Actually that was the first thing he said to me. I’m like, ‘Yo, what’s up.’ He’s like, ‘Yo, I love your dad, man.’ And then he said, ‘Yo, I’m a big fan.'"
From that moment forward, it was mutual respect and love. "But that’s when I was like, ‘Oh, shit.,'" continued Sean. "So when I told Dave I was working on the album for Detroit, he was like, ‘Bro, not only will I do the skit, I’ll come out and do a show with you. You know, I’ll come out and support you just ’cause I believe in you.’ So I appreciate him for being on that level of humility still when he is who he is."