#2 Vito

When Vito made his big splash in the WWE, he did so with help, appearing as one member of the Full Blooded Italians.
Together, the FBI were a solid mid-card stable on SmackDown, often helping more established superstars, from the Big Show to the chairman himself - Vince McMahon.
But when the group reunited, though just Nunzio and Vito this time, the big man started wrestling in a dress, much to the horror of his partner.
The story was not handled well, with the commentators in fits of laughter over the idea of a man in a dress.
To his credit, Vito would really make the gimmick work, often appearing outside of the company in a dress to make it seem legit.
Despite his efforts, no-one took him seriously, and he quickly left the company not long after.