#6 Jesse Ventura
Jesse Ventura was first a wrestler who later transitioned to the commentary booth in WWE, commentating alongside current WWE Chairman Vince McMahon. But, it was not always hunky-dory between the two.
Jesse Ventura and Vince McMahon were at loggerheads in WWE in the late 80s as Ventura was unhappy at not being paid royalties. Ventura famously sued WWE and won the case, with the federal court awarding him $801,333 in that case.
He had also tried to unionize the WWE locker room, which didn't go down well with Vince, who threatened to fire Ventura. Here's what Ventura said about why he sued McMahon:
Vince wasn't truthful, because I would ask and Barry Bloom would always ask about videotape royalties, because I got paid for them in Hollywood. Vince kept saying he didn't pay royalties. Had that been true, he'd have won. Nobody requires him to pay them. During discovery, we found out that Hogan, Cyndi Lauper, Mr T. got royalties. Certain people were getting them, then they would lie to everyone else.
The duo have now mended their relationship, with Ventura appearing a few times on WWE television over the last 20 years and was even inducted into the WWE Hall of Fame.