I sent like a minute clip of the build to this and the jump to a friend of mine who hasn’t watched wrestling since the Attitude Era. He asked what the trash can accomplished and I let him know it was to give representation to Grouch Culture.
The weirdest is Bradley Cooper appearing post Hangover in the guest host era. He wasn't as big as he ended up, but he was still fairly well known by then. Kristin Wiig is another wtf celeb appearance on Raw promoting MacGruber the year before Bridesmaids came out. She was already pretty big by 2010 though with her overrated SNL skits playing 13 versions of the same character capturing the public's eye.
I feel like Sam Jackson's sole WWE appearance should be a bigger deal.