#1 James Dudley
Who? You would be forgiven if you do not recognise the name of James Dudley. No one knew who he was back in 1994 either when he was announced as an inductee in that year's Hall of Fame class.
Dudley was Vince McMahon Sr's limo driver. That was almost the only service he provided to the McMahon family. Unless the company plan to add a "Limo Driver Wing" to it's Hall of Fame, then his induction will remain the most ridiculous in WWE history.
WWE's revisionist history has attempted to bulk up Dudley's credentials by claiming he was the first African-American to run a major arena in the United States as a promoter but in reality he performed largely menial tasks backstage such as counting ticket sales and acting as a glorified gopher for the McMahon family.
By all accounts he was a pleasant man, was loyal, worked hard and never complained and thus the McMahon's way of thanking him was to award him a Hall of Fame berth.
For those people who believe in the Hall of Fame as a pinnacle of one's profession, Dudley's induction is one that sits well with virtually nobody.