#1 The Boogeyman - WWE Brand Ambassador
While The Boogeyman wasn't the most successful wrestler in WWE championships-wise, he is without question one of the most memorable performers of the 2000s -- most fans still vividly remember The Boogeyman's creepy antics and infamous worm eating.
Despite getting a late start to his professional wrestling career at the age of 40, The Boogeyman still managed to carve a great niche out for himself in the WWE as the company's creepiest Superstar -- The Boogeyman had many awesome moments throughout his short career.
Boogeyman would remain a WWE Superstar up until his release from the company in 2009, and he would go onto perform occasionally on the Indies. As of 2015, The Boogeyman has been signed to a "Legends Contract" where he appears on television infrequently, and he also serves as a brand ambassador.