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Last week on Monday Night Raw, Wiz Khalifa—apparently blazed out of his mind—showed up as the musical guest for the evening. It’s not entirely unprecedented—after all, Khalifa collaborated with John Cena on the soundtrack to WWE 2K15but it was certainly an odd, awkward sight. There was that dodgy musical performance to the tragically white crowd. There was that Mizdow freestyle sketch backstage. And, of course, there was that really awkward handshake between Khalifa and Vince McMahon. Vince seemed nervous, like a freed animal that’s looking to bolt at the first window of opportunity.

The WWE rarely collaborates with rappers, unless you count the numerous rapper gimmicks over the years. But, really, they ought to collaborate more, because the few rapper guest spots have been reliable crowd pleasers. Here, for your viewing and listening pleasure, is a History of Rappers Performing on WWE. Let’s break it down.