#2 Booker T and Sharmell vs. The Boogeyman (WrestleMania 22)

Booker T’s story in WWE is an odd one. He came in as the WCW Champion and was quickly reduced to cannon fodder for the “real” stars of the WWF. He fought a match over shampoo in his first WrestleMania.
He actually made it up to the status of wrestling for one of the World Titles in his second WrestleMania but was embarrassed in defeat after losing a match that followed over a month of being harassed by racially insensitive remarks from the Champion (Triple H).
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He went on to have some success as a tag wrestler and won the tag titles with RVD, even successfully defending them on his third WrestleMania. He had a ridiculously stupid feud against The Undertaker that saw him try to use voodoo to beat the Deadman, only to be squashed and made to look like a fool.
His fourth WrestleMania appearance was in a battle royal that was untelevised, but at least he won! That was WrestleMania 21. Oh, and let’s not forget that storyline where Kurt Angle wanted to have “beastiality sex” with Booker’s wife!
Then, we come to WrestleMania 22. Booker T and his wife had been taunted and chased around by the worm-eating Boogeyman for a few weeks and ended up in a handicap match against him at the Show of Shows, which they lost. Good lord. It was an embarrassing time to be a Booker T fan.
He would eventually get a World Title run, as he won the King of the Ring later that year and shortly after would win the World Heavyweight Title. That was a good time to be a fan of Booker T, but sadly he would be gone from WWE about one year later.
His biggest WrestleMania moments were being defeated to end a feud that saw him repeatedly get put down for being black, and losing a 3-minute match that ended with him being covered in live worms. Oy.