#4 Jesse Ventura
He's been a governor, a movie star, and a TV host, but many wrestling fans remember Jesse Ventura for his long stint as an announcer for WWE.
Jesse was the first announcer to really put down the babyfaces while outright rooting for the heels. For example, when face Ken Patera seemed on the verge of beating Dino Bravo in a tug-o-war, Jesse stated that Patera must have greased the rope on Bravo's end, because 'that's the kind of thing you learn in prison.'
A top AEW star just called one of his colleagues 'spoiled' and 'narcissistic' HERE.
Ventura also did not care in the least that Vince was his boss. He still laid into McMahon heavily, and their back and forth was one of the most entertaining aspects of watching the WWE in the 1980s. Jesse loved to tease Vince about how his opinion didn't matter since he'd never been a wrestler. He also called Vince's arms 'pipe cleaners' and alluded to his nerd status.
Ventura eventually moved on to Hollywood roles--such as his widely regarded turn in Predator--and even became Governor of Minnesota. These days he does his fighting on social media as a Social Justice Warrior, but fans will always remember the way he lit up the announce booth with his conniving ways.