#1 Chris Jericho

Despite Kane's accomplishments in Royal Rumble matches, Chris Jericho is the one wrestler who should have won a Royal Rumble. For starters, he is the ultimate iron man in Royal Rumble history after lasting around 5 hours across all of his Rumble stints combined, which is more than anybody.
Jericho has lasted the longest in multiple Royal Rumble matches, including his last one in 2017. He probably should have won that year as well, as his program against Kevin Owens was worthy of a world championship feud at WrestleMania.
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However, Jericho's name shouldn't even be on this list, as he was penciled to win the 2012 Royal Rumble match. But probably because they wanted to go with a shocking conclusion, WWE ended up booking Sheamus to win, leaving Jericho without that elusive Rumble win.
His surprise return at number 2, followed by a 50-minute stay, in 2013 was another memorable Royal Rumble moment for Le Champion. But Chris Jericho remains without a victory in this match. For the amount of time he spent on aggregate, WWE should have stuck with Jericho to win the 2012 edition despite it being predictable.
When has that ever stopped WWE in booking recent Rumble winners?