Thank you!
Was looking for any Sci-Fi connections for Howard Stern and found him in Men in Black 3, where he appears as one of the detainees in the 1969 MIB headquarters. He can be spotted at the bottom right, just after Agent J (Will Smith) wakes from travelling back in time to 1969.
Official Trailer link with timestamp:
Screenshot:
YeS! Lets talk about this more. Whats going on? It completely breaks a well established pattern.