#2 Jim Ross
Jim Ross is the most colourful commentator in the WWE, and in the pro wrestling business. During his time in the WWE, he was loved for his work, while outside WWE, he has created a niche for himself through his entrepreneurship.
He started the BBQ sauce and its related products business, after being released from WWE as part of a storyline. During his spare time, he thought of ways to venture into something in line with his own taste and the state of Oklahoma.
The state is known for its barbecue habits, and Jim decided to use the same to his advantage. His products are loved by fans, and you can see their response by visiting his Twitter handle.
There is still speculation he would return to commentate a match at WrestleMania, and if he does, as he did for The Undertaker versus Roman Reigns match at WrestleMania 33, we would be in for a treat.