#2 Kane

Glenn Jacobs has had an illustrious Royal Rumble career. He has entered the match 19 times, with his best efforts obviously coming as Kane. The Big Red Machine has done everything in a Rumble match, except winning it. This is an unfortunate shame, even more so than the Big Show.
Kane has constantly entered the Royal Rumble and cleaned house, being an ever-present threat to the favorites of the match. He even has a record total of 44 eliminations to his name in these matches.
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A quarter of those came in Kane's greatest ever Royal Rumble performance in 2001, where he entered at number 6, eliminated 11 Superstars and was the runner-up to 'Stone Cold' Steve Austin. It might just be the greatest individual showing in Rumble history.
Kane has come close on another few occassions but was never able to pull it off. He should have had at least one Royal Rumble to his name, after his contributions to the match. The quote, "Always the bridesmaid, never the bride" has never been so apt.