#2 Jillian Hall's bad singing career
Despite being a solid hand in the ring, Jillian Hall's time on the main roster wasn't much, with her biggest accolade being winning the Diva's title for minutes in 2010.
Outside of her brief title flutter, Hall is perhaps best remembered for her pop-diva character, who believed she could sing, much to the horror of the fans who could hear her.
Whilst many thought this was a parody of Britney Spears, Hall's character was reportedly a rib on Brooke Hogan, the daughter of Hulk Hogan who had failed to make it as a singer despite multiple opportunities.
The WWE still had beef with the Hulkster after his abrupt departure in 2006, and found making fun of the former World Champion's daughter as vengeance, though some would argue, very petty.