Eminem has an affinity for name-dropping pop culture figures in his raps and one person who has been mentioned multiple times over the years is embattled music mogul Diddy.

Shady first mentioned Puff on wax when Em was still a little-known independent artist on the unreleased 1996 song “F**king Crazy.”

“Original bad boy on the case/Cover your face/Came in the place blowed and sprayed Puffy with mace,” Em raps on the track, making a funny double entendre.

Over the years, Eminem has continued to mention Diddy in raps. Most recently, Em’s tone has changed toward Puff in the wake of the Bad Boy founder being sued multiple times for sexual assault. On the song “Fuel” from Slim’s latest album, The Death of Slim Shady (Coup de Grâce), Em makes references the rape allegations against Diddy and his speculated involvement in the death Tupac’s death.

“Do not test like an essay (Why?)/’Cause like where my homies out West, aye (Yeah),” Em raps. “We can just say (What?)/I’m like an R-A-P-E-R/I got so many S-As/S-As/Wait, he didn’t just spell the word rapper and leave out a ‘P’, did he?/Yup/R-I-P, rest in peace, Biggie/And ’Pac, both of y’all should be living/Yup, but I ain’t tryna beef with him ’cause he might put a hit on me like Keefe D, get him/And that’s the only way you’re gonna be killing me (Nah)/Ain’t gonna be on no beat, silly (Yeah).”

Check out Eminem’s witty and crass lyrics about Diddy over the years below.

See All the Witty and Crass Times Eminem Dissed Diddy in His Lyrics