#1. Took years to win over Vince McMahon: The Miz

The Miz's relationship with Vince McMahon has grown over the years. His entry into WWE and eventual rise to the top is arguably one of the most underrated stories of the past decade. He came into WWE at the age of 24 via Tough Enough - a competition that he didn't win.
Even then, he was offered a developmental contract, and two years later, he made his debut on the main roster. The Miz recalled a story where he botched a promo and thought he was going to be fired, only for Vince McMahon to assure him he wouldn't:
“I remember going backstage thinking, ‘I’m going to get fired,’” he said. “And I walk back, I went over to Vince, I go, ‘I’m so sorry, I apologize, this will never happen again. I will make sure it will not happen again.’ He goes, ‘I know it won’t happen again.’ He took me aside and he said, ‘Bullet points, kid. You need to learn bullet points, and I know you will do better next time because you will have to do it next Friday.’ So it was like, ‘Oh, I’m not fired.’”
The Miz has had to go through a lot in WWE, including getting kicked out of the locker room by Chris Benoit. Eventually, Vince McMahon recognized him enough to make him a Money in the Bank winner, a WWE champion, and subsequently, a WrestleMania main eventer.
While WrestleMania 27 might have been the pinnacle of The Miz's career, he has gone on to enjoy great success and is a WWE Grand Slam Champion. Vince McMahon's trust in The Miz has been repaid and more with an incredible 15-year tenure on the main roster.