I dunno, him and Coolio had some beef in the 90s. When Weird Al parodied Coolio’s Gangsters Paradise with his Amish Paradise Weird Al didn’t do so with the consent of Coolio. Gangsters paradise was a deeply personal song to Coolio so he was understandably upset. As a direct parody it was protected under fair use but Weird Al didn’t feel right about it. So he reached out to Coolio, apologized and ever since then Weird Al has gotten the artist approval to parody their work despite the fact he doesn’t need to. Coolio did eventually come around and agree it was a pretty funny parody. Plot twist, (not really) that’s how humble Weird Al is, he didn’t do anything legally wrong and yet he still recognized he could do better.