20. King Booker
Here Yee, Here Yee it is I, King BOOKA!!!
The five-time, five-time, FIVE-time (get the picture) WCW World Champion Booker T had somewhat of an underwhelming early WWE career. Particularly, he is best remembered during this period for losing that WrestleMania 19 match with Triple H, amidst the controversial feud where The Game tyrannically proclaimed that people like Booker were only employed to dance for people like him.
Yikes, that’s enough of that.
It was only after years in midcard purgatory that Booker finally
received his crowning achievement by winning the 2006 King Of The Ring
Tournament, and soon after the World Heavyweight Championship. With
this, he ascended on the run of his career as King Booker, a pompous
English king with his Queen Sharmell in tow. It was a brilliant gimmick, which completely revitalized The Book Man. Not to mention, his character was one of the few times WWE successfully integrated comedy into a main event act during the Ruthless Aggression Era.
Most recently, King Booker donned his royal robe on a 2018 SmackDown episode in a segment with The New Day who had just won their fifth Tag Team Championship, because five time.
WWE loves busting out Booker for a Spinaroonie now and then, and a royal roonie on the Grandest Stage of Them All wouldn't go astray.