20. Bo Dallas
Sometimes, things work in NXT because they develop there organically. Bo Dallas was originally a scrappy babyface (remember his microfeud with Wade Barrett?) but he slowly got smarmier as the crowd turned on him.
Eventually, he was this bizarre, terrified narcissist who thought that hand-written letters from fans could be redeemed for title shots and that the best way to go incognito was to walk around in a mask shouting “I AM NOT BO DALLAS”. Full Sail wanted to see him get his comeuppance SO BAD.
And they did, and sent him packing to Raw, where he debuted as “The Inspirational” Bo Dallas. Now, the average 2013 Raw viewer was barely aware that NXT existed, so they had zero priming for Bo Dallas. Without being privy to all his development, all they saw was a weirdo who wrestled in tighty-whities, talked like a little girl and spoke in puns.
If that's all you knew about him - and it was, provided you weren't watching NXT - he sounds like he should be fighting Adam West instead of Ron Killings.
WWE had no idea what to do with him, either, which is why his two career highlights (knocking over El Torito doing a victory lap and morphing into Bo Rida) are like two years apart.