Perhaps one of Vince's biggest challenges was the creation of the People's Champ The Rock. I mean here he have a third generation star with all the charisma and athletic ability in the world but he is still getting booed.
So Vince decided to drop the whole warrior gimmick and blue trunks, and re package him into a cocky Anti-Hero similar to that of Randy Orton. The Rock finally had the breathing space to showcase his talents to the world without the pressure of been known as Rocky Johnson's son. he immediately made an impact by becoming the youngest and first Samoan wrestler to win the IC Championship.
The crowd never no how to react by this I mean although the Rock was an A** they loved him. Vince fed on the electricity that the Rock was garnering from every arena he went to and used it to his advantage. He made the Rock into a superstar by having him dethrone the legendary Ron Simmons from the Nation of Domination.
Feuds with Foley, HHH and Austin would help him develop his in ring chemistry with wrestlers as well as the audience. his unique ability to capture the audiences attention just by using his words made him into a cultural icon, with rappers and actors world wide using his various catch phrases in moves, songs and commercials.
Rock owes Vince hugely, by becoming a great wrestler it allowed him to branch into Hollywood, after his first solo movie the Scorpion King, the rock became one of the most wanted stars in Hollywood and is currently filming his new move the Fast and Furious 5.