#1 Curt Hawkins refused to end his losing streak in WWE
The final entry on this list is a man who made losing a match so popular that the WWE Universe came to enjoy watching him lose. Yes, we are talking about Curt Hawkins, whose losing streak in WWE might never be broken by anyone in the future.
Curt Hawkins returned to WWE in 2016 and while it looked like WWE might push him as a top Superstar, it was the opposite that happened as he kept on losing matches continuously. Speaking to the Sam Roberts Podcast, Hawkins revealed an occasion when he begged WWE to let him lose a match on Main Event.
“My main priority has always to do the best that I can, in whatever situation that I have been placed in. I have always tried to do my best, whatever match I am in I try to steal the show in regards to what I am allowed to be doing...What really sparked it all was that there was some online article that said that Curt Hawkins just lost his 100th match in a row. I think that, I’m not taking shots at anyone else, but most of my colleagues would be upset at that sort of thing.
“There’s been times since that article where I was having matches; in particular I had a match on Main Event against Heath Slater that I was supposed to win, but I thought, wait, hold it, no, please, no. This could be something. There’s no sense in ending this story on Main Event. Who begs to lose matches? I literally did that, though, where I said that I can’t win matches, and they were cool about it. In the first place, they were telling me that I did a good job and that I am going to win a match. But I was like, no, you don’t understand.”
Hawkins' 269-match losing streak finally ended at WrestleMania 35 when he won the RAW Tag Team Championship with Zack Ryder - which was certainly a bigger stage than a random episode of Main Event!